XII Copernican International Young Scientists...

1

2

XII Copernican International Young Scientists Conference organized by

Faculty of Chemistry, Nicolaus Copernicus University in Toru, Poland

Toru 2018

The study includes: Abstracts of materials presented in the form of oral presentations and posters during the XII Copernican International Young Scientists Conference. Publication is based on the abstracts provided by the authors. Authors of individual abstracts are responsible for the content and substantive value.

Typesetting and proofreading:

PhD A. FilipiakSzok MSc J. Gromowska MSc S. Kowalska MSc M. PlaskaczDziuba

Graphic design of the cover: Msc M. wikliska

Publication of the conference materials is funded by the President of the City of Toru.

3

Conference organizer: Faculty of Chemistry NCU in Toru, Poland Local Organizing Committee: Prof. DSc E. Szyk Dean of the Faculty of Chemistry Prof. DSc H. Kaczmarek, DSc I. akomska, prof. NCU, DSc J. cianowski, prof. NCU DSc U. Kiekowska PhD M. Kurzawa PhD A. FilipiakSzok MSc J. Gromowska MSc S. Kowalska MSc M. PlaskaczDziuba

Scientific Committee: Prof. DSc E. Szyk Dean, Faculty of Chemistry NCU Prof. DSc S. Koter DSc R. GadzaaKopciuch, prof. NCU DSc B. Omiaowski, prof. NCU DSc J. cianowski, prof. NCU DSc A. Bajek DSc Sz. Bocian DSc A. Katafias DSc U. Kiekowska DSc M. Ligor DScA. Nowaczyk DSc J. Nowaczyk DScK. Roszek DSc S.K. Studziska DSc M. Szumski DSc I. Szymaska DSc G. Wrzeszcz PhD M. Barwioek PhD M. Cichosz PhD J. Czarnecka PhD. A. Jastrzbska PhD A. Kmieciak PhD J. Kozowska PhD M. Kurzawa PhD P. Pciennik PhD Z. Rafiski PhD J. SkopiskaWiniewska PhD P. Szczepaski PhD M. SzultkaMyska PhD A. Topolski PhD A. Zawadzka

Special Guest: Prof. DSc Jolanta B. Zawilska, Head, Department ofPharmacodynamics Medical University of d, d, Poland Honorary Patronage:

Marshal of the KuyavianPomeranian Voivodeship

Piotr Cabecki

President of the City of Toru

Micha Zaleski

Rector Magnificus NCU in Toru

Prof. DSc Andrzej Tretyn

Dean of Faculty of Chemistry

Prof. DSc Edward Szyk

Scientific publishing, Nicolaus Copernicus University

Polish Chemical Society

Association of Engineers and Technicians

of Chemical Industry

Polish Physical Society

MEDIA PATRONAGE

SPONSORS

4

S

PONSORS

SCHEDULE

5

SCHEDULE

6

THURSDAY 28.06.2018

8.00 10.00 Conference Registration

10.00 10.10 Opening Ceremony - E. Szyk - Dean, Faculty of Chemistry, NCU (Auditorium I)

10.10 11.10 Keynote Lecture DSc Jolanta B. Zawilska, Medical University in d, "Novel psychoactive substances: from chemical structure to biological actions"

11.10 11.25 Grzegorz Trykowski - Faculty of Chemistry, NCU, Central Laboratory (Instrumental Analysis Laboratory), Alchem, Linegal Chemicals, Merck

11.25 11.40 Coffee break

Analytical Chemistry Panel

Chemical Technology & Organic Chemistry Panel

Environmental Science Panel

Inorganic & Coordination Chemistry Panel

Molecular Biology & Medical Science Panel

Thermodynamics, Simulations, Quantum Mechanics & Optoelectronics Panel

Oral presentations (Lecture room 80) 11.45 12.45 Chairmen: Prof. dr hab. E. Szyk Dr M. Kurzawa

1. Katarzyna Willkosz 2. Kamila Kdziora-Koch 3. Jakub Matusiak 4. Katarzyna Domaska 5. ukasz Nuckowski

Oral presentations (Lecture room 61A) 11.40 13.00 Chairmen: Dr hab. J. cianowski, prof. UMK Dr Z. Rafiski

1. Andrzej Nowok 2. Monika Skibiska 3. Grzegorz Wilkowski 4. Karolina Kowalska 5. Aleksandra Piontek 6. Aneta Kaczor 7. Aneta Kurpanik

Oral presentations (Auditorium II) 11.40 13.10 Chairmen: Dr hab. J. Nowaczyk Dr M. Cichosz

1. Kinga lsarczyk 2. Monika Zajkaa 3. Karina Kocot 4. Adrianna Grobelna 5. Aleksandra Wasiluk 6. Anna Adamska 7. Ewelina Janicka 8. Barbara Ksicka

Oral presentations (Lecture room 57) 11.45 12.55 Chairmen: Dr hab. A. Katafias Dr M. Barwioek

1. Natalia Tereba 2. Maja Zakrzyk 3. Jan Lorkowski 4. Marta Chrzanowska 5. Kinga Stefanowska 6. Agnieszka Gilewska

Oral presentations (Auditorium I) 11.40 13.10 Chairmen: Dr hab. K. Roszek Dr Joanna Czarnecka

1. Magorzata Witkowska 2. Pamela Krug 3. Pawe Jonczyk 4. Katarzyna Kwiatkowska 5. Natalia Stachowiak 6. Agata Krzak 7. Sylwia Matysiak 8. Barbara asut

Oral presentations ( Lecture room 81) 11.45 12.55 Chairmen: Prof. dr hab. S. Koter Dr A. Zawadzka Dr P. Pciennik

1. Aleksander Khreptak 2. Olimpia Rybacka 3. Sylwia Kutya 4. Marcin R. Zema 5. Ewelina Kwiatkowska 6. Witold Waecki

13:00 14.00 Lunch break (Faculty of Law and Administration Authorities)

SCHEDULE

7







Oral presentations (Lecture room 80) 14.15 15.05 Chairmen: Dr hab. M. Ligor Dr hab. S.K Studziska

1. Agnieszka Szwagierek 2. Elbieta Szczepaska 3. Anna Kaczmarkiewicz 4. Jakub P. Sk

Oral presentations (classroom 61A) 14.15 15.35 Chairmen: Dr hab. U. Kiekowska Dr A. Wolan

1. Justyna Gromowska 2. Ewelina Bystrzycka 3. Paulina Biedka 4. Andrzej Dzienia 5. Donata Kuczyska 6. Magdalena Konefa 7. Edyta Rynkowska

Oral presentations (Auditorium II) 14.15 15.45 Chairmen: Dr hab. J. Nowaczyk Dr M. Kurzawa

1. Urszula Kwasigroch 2. Agata Kostrzewa 3. Weronika Masowska 4. Agata Nowak 5. Agnieszka Bracawska 6. Klara Nestorowicz 7. Iga Jankowska 8. Agnieszka Jdruch

Oral presentations (Lecture room 57) 14.15 15.15 Chairmen: Dr hab. A. Katafias Dr A. Topolski

1. Ksenia Szmigiel 2. Jagoda Ryba 3. Sylwia Cukrowicz 4. Mateusz Kowalik 5. Patrycja Rogala

Poster sesion (lobby near AuditoriumI) 14.15 15.15 Chairmen: Dr hab. A. Nowaczyk Dr J. Kozowska

1. Ewelina Pankanin 2. Ewelina Pankanin 3. Anna Kleczka 4. Anna Kleczka 5. Magorzata Witkowska 6. Pamela Krug 7. Justyna Brodowicz 8. Boena Kukla 9. Szymon Tott 10. Anna Koodziej 11. Katarzyna Lorek 12. Agata Krzak 13. Katarzyna Tomczyk 14. Eliza Romaczuk 15. Sylwia Wojda 16. Paulina Mitkowska 17. Robert Dec 18. Agnieszka Talik 19. Filip A. Fedak 20. Ieva Gudzinskaite 21. Katarzyna Nowak 22. Sylwia Berbe 23. Jagoda Barczyk 24. Paulina Mazur 25. Katarzyna

Wgrzynowska - Drzymalska

Poster sesion (lobby near AuditoriumI) 14.15 15.15 Chairmen: Dr A. Zawadzka Dr P. Pciennik 1. Aleksander Khreptak 2. Sylwia Ziba 3. Marcin Roland Zema 4. ukasz Marek 5. Kamil Korzeniowski 6. Witold Waecki 7. Hubert Jwiak 8. Dawid Heczko 9. Marcin Czapla 10. Micha Chodkowski 11. Magdalena Szaniawska 12. Anna Taraba 13. Maria Marczak 14. Olimpia Rybacka 15. Adam Mizera 16. Adam Mizera 17. Magorzata Widelicka 18. Magorzata Widelicka 19. Karol Rytel 20. Karol Rytel 21. Klaudia Osiska-Basaaj 22. Klaudia Osiska-Basaaj

Coffee break

SCHEDULE

8







Poster sesion (lobby near AuditoriumI) 15.10 16.10 Chairmen: Dr A. Jastrzbska Dr M. Kurzawa

1. Justyna Jonik 2. Justyna Jonik 3. Katarzyna Willkosz 4. Kamila Kdziora-Koch 5. Jakub Matusiak 6. Sylwia Kowalska 7. Katarzyna Domaska 8. Agnieszka Szwagierek 9. Elbieta Szczepaska 10. Piotr Ziobrowski 11. Dobrochna Rabiej 12. Anna Filipiak-Szok 13. Anna Filipiak-Szok 14. Marta Staczyk 15. ukasz Magda*

Poster sesion (lobby near AuditoriumI) 15.40 16.40 Chairmen: Dr hab. U. Kiekowska Dr Z. Rafiski Dr A. Wolan

1. Andrzej Nowok 2. Monika Skibiska 3. Karolina Kowalska 4. Aleksandra Piontek 5. Edita Zubryt 6. Anna Wgrzyk 7. Alicja Walcka-Kurczyk 8. Paulina Chaupnik 9. Izabela Zabocka 10. Donata Kuczyska 11. Monika Machnik 12. Ewa Kisiel 13. Ewelina Salamon 14. Ewelina Salamon

Poster sesion (lobby near AuditoriumI) 16.00 17.00 Chairmen: Dr M. Szultka-Myska Dr P. Szczepaski

1. Magdalena Czemierska 2. Magdalena Czemierska 3. Kinga lsarczyk 4. Lidia Szymkowiak 5. Joanna Sokoowska 6. Mikoaj Rogula 7. Anna Adamska 8. Barbara Ksicka 9. Marta Gellert 10. Weronika Masowska 11. Agnieszka Bracawska 12. Marta Plaskacz-Dziuba 13. Klara Nestorowicz 14. Sandra Saunorit 15. Kamila Brylewska 16. Anna Litwin 17. Karolina Poe 18. Marta Nowak 19. Marta Nowak 20. Ewelina Janicka 21. Monika Bal

Poster sesion (lobby near AuditoriumI) 15.20 15.50 Chairmen: Dr M. Barwioek Dr A. Topolski 1. Maja Zakrzyk 2. Karina Kocot 3. Jan Lorkowski 4. Marta Chrzanowska 5. Mateusz Jakubowski 6. Kinga Stefanowska 7. Grzegorz Wilkowski

Oral presentations ( Auditorium I) 15.30 16.50 Chairmen: Dr hab. K. Roszek Dr J. Skopiska - Winiewska

1. Katarzyna Wgrzynowska - Drzymalska

2. Katarzyna Tomczyk 3. Dorota Konarzewska 4. Paulina Mitkowska 5. Agata Kaczyska 6. Wesam Ali 7. Aldona Minecka

Oral presentatons ( Lecture room 81) 15.30 16.50 Chairmen: Dr A. Zawadzka Dr P. Pciennik

1. Marcin Czapla 2. Micha Chodkowski 3. Magdalena Szaniawska 4. Anna Taraba 5. Maria Marczak 6. Sylwia Ziba 7. Hubert Jwiak

18:30 19.30 Guide tours in the Old Town of Toru

20.00 23.00 BBQ Party (Faculty of Chemistry)

21.30 -22.00 Chemical Demonstrations

SCHEDULE

9

FRIDAY 29.06.2018

7.30 9.00 Conference Registration







Oral presentations (Lecture room 80) 9.00 9.50 Chairmen: Dr hab. R. Gadzaa-Kopciuch, prof. UMK Dr M. Kurzawa

1. Justyna Ubysz 2. Sylwia Kowalska 3. Justyna Zuziak 4. Katarzyna Jedliska

Oral presentations (classroom 61A) 9.00 10.10 Chairmen: Dr hab. B. Omiaowski, prof. UMK Dr A. Kmieciak 1. Piotr Lewiski 2. Monika Szymaniak 3. Micha Wicaw 4. Dominika Zaubiniak 5. Micha Wrzecionek 6. Krzysztof Dzieszkowski

Oral presentations (Auditorium II) 8.00 9.45 Chairmen: Dr hab. S.K. Studziska Dr hab. M. Szumski

1. Dariusz Kulus 2. Karolina Czarny 3. Anastazja Krzyanowska 4. Przemysaw Tomczyk 5. Dominika Gajewska 6. Anna Pudeko 7. Emilia Stakowska 8. Anna Abramowicz 9. Kamila Brylewska

Oral presentations (Lecture room 57) 8.00 9.10 Chairmen: Dr hab. I. Szymaska Dr hab. G. Wrzeszcz

1. Agata Olszewska 2. Edyta Pko 3. Weronika Strzempek 4. Maciej Strzempek 5. Ewelina Mackiewicz 6. Marcin Saski

Oral presentations (Auditorium I) 8.00 10.00 Chairmen: Dr hab. A. Bajek Dr J. Czarnecka

1. Justyna Czarna 2. Mikoaj mudziski 3. Sylwia Modrzycka 4. Agnieszka Szemraj 5. Dominika Rymarz 6. Karolina Stachurska 7. Aleksandra Dawidziak 8. Ewa Czechowska 9. Beata Kaczmarek 10. Gabriela Bernatowicz

Coffee break

SCHEDULE

10







Poster sesion (lobby near AuditoriumI) 10.00 11.00 Chairmen: Dr A. Jastrzbska Dr M. Kurzawa

1. Justyna Ubysz 2. Justyna Zuziak 3. Katarzyna Jedliska 4. Paulina Bierzuska 5. ukasz K. Kaczyski 6. Jarosaw Wojciechowski 7. Anna Rzuchowska 8. Arkadiusz Nowicki 9. Ludwika Kolec - Janiak 10. Martyna Baranowska 11. Wiktoria Zgagacz 12. Mindaugas Liaudanskas 13. Mindaugas Liaudanskas

Poster sesion (lobby near AuditoriumI) 10.20 11.20 Chairmen: Dr hab. Omiaowski, prof. UMK Dr A. Kmieciak 1. Monika Szymaniak 2. Micha Wicaw 3. Micha Wrzecionek 4. Paulina Baziska 5. Andrzej Dzienia 6. Magorzata Dziubaniuk 7. Justyna ucka 8. Aneta Kurpanik 9. Dominika Zaubiniak 10. Justyna Gromowska 11. Takuma Hosaka 12. Ewelina Bystrzycka 13. Daria Kosmalska 14. Daria Kosmalska

Oral presentations (Auditorium II) 10.00 10.40 Chairmen: Dr hab. J. Nowaczyk Dr M. Szultka-Myska

1. Anna Litwin 2. Piotr Kowal 3. Barbara Flasz

Poster sesion (lobby near AuditoriumI) 9.15 10.15 Chairmen: Dr hab. I. Szymaska Dr hab. G. Wrzeszcz

1. Agata Olszewska 2. Weronika Strzempek 3. Maciej Strzempek 4. Ewelina Mackiewicz 5. Kohei Kobayashi 6. Marcin Saski 7. Karolina Dysz 8. Ksenia Szmigiel 9. Jagoda Ryba 10. Sylwia Cukrowicz

Oral presentations (Auditorium I) 10.15 11.40 Chairmen: Dr A. Bajek Dr J. Skopiska - Winiewska 1. Kinga Nadolna 2. Robert Dec 3. Magdalena Surman 4. Joanna Duda-Goawska 5. Sylwia Berbe 6. Katarzyna Chamera 7. Jagoda Barczyk







Poster sesion (lobby near AuditoriumI) 11.00 12.00 Chairmen: Dr hab. Sz. Bocian Dr hab. M. Szumski

1. Karolina Mynarczyk

2. Karolina Mynarczyk

3. Dariusz Kulus

4. Karolina Czarny

5. Anastazja Krzyanowska

6. Przemysaw Tomczyk

7. Dominika Gajewska

8. Emilia Stakowska

9. Anna Abramowicz

10. Robert Baron

11. Pawe Rogala

12. Piotr Kowal

Poster sesion (lobby near AuditoriumI) 11.45 12.45 Chairmen: Dr hab. A. Nowaczyk Dr J. Kozowska

1. Joanna Hoowko 2. Joanna Hoowko 3. Daniel Styburski 4. Daniel Styburski 5. Magdalena Gbicka 6. Magdalena Gbicka 7. Gabriela Gajek 8. Gabriela Gajek 9. Dorota Cheminiak -

Dudkiewicz 10. Barbara Wysocka 11. Ewa Kot 12. Agata Kaczyska

SCHEDULE

11

* in absentia participant

13. Nina Rdzia

14. Barbara Flasz

15. Monika Nowak

16. Monika Nowak

17. Aneta Wjcik

18. Aneta Wjcik

19. Katarzyna Mode * 20. Micha Kropkowski *

13. Micha Szewczuk 14. Iwona Atyn 15. Miosz Zajczkowski 16. Barbara Kocielniak

- Merak 17. Olga Madejczyk 18. Karolina Stachurska 19. Joanna Strumillo 20. Aleksandra Dawidziak 21. Katarzyna Ratajczak 22. Ewa Czechowska 23. Kinga Nadolna

12.45 13.45 Coffee break

14.00 14.30 Closing Ceremony of the Conference along with prize giving (Auditorium I, Faculty of Chemistry)

14.45 16.00 Lunch break (Faculty of Law and Administration Authorities)

XII COPERNICAN INTERNATIONAL YOUNG SCIENTISTS CONFERENCE - INAUGURAL LECTURE

12

NOVEL PSYCHOACTIVE SUBSTANCES: FROM CHEMICAL STRUCTURE TO BIOLOGICAL ACTIONS

Prof. DSc Jolanta B. Zawilska

Department of Pharmacodynamics, Medical University of d, d, Poland

Over the last decade a rapidly increasing number of novel psychoactive substances (NPSs), often marketed as legal/herbal highs, synthetic/designer drugs, smoking blends, bath salts, plant food, insect repellents, research chemicals, air fresheners, jewelry cleaner, pond water cleaner and collectible products, has appeared on the drug market in an effort to bypass controlled substance legislation. An NPS is defined as a new narcotic or psychotropic drug, in pure form or in preparation, that is not controlled by the 1961 United Nations Single Convention on Narcotic Drugs or the 1971 United Nations Convention on Psychotropic Substance, but which may pose a public health threat comparable to that posed by substances listed in these conventions. These substances are psychoactive in that they stimulate or inhibit the function of the central nervous system. The European Union Early Warning System notified the appearance of more than 620 new psychoactive substances during the period of May 2005 October 2017. NPSs are often sold with the disclaimer: not for human consumption, not tested for hazard and toxicity, protect from children or for research purposes only. Based on the spectrum of their actions on cognitive processes, mood, and behavior, NPSs can be classified into six basis categories: amphetamine- and ecstasy-like stimulants, synthetic cannabinoids, hallucinogenic/dissociative, opioid-like compounds, sedative/anxiolytics, and others. NPSs may, however, exhibit a combination of these actions due to their designed chemical structure. The great majority of NPSs are synthetic compounds, and some of these were initially designed as potential medicines or pharmacological tools.

NPSs can produce a wide spectrum of life-endangering side-effects. Some of these actions are specific to a certain compound or group of compounds, while others can be produced by drugs from different classes of NPSs. In addition to psychiatric (irritability, anxiety, agitation, aggression, panic attacks, lack of motivation, anhedonia, depression, dysphoria, paranoid delusion, visual and auditory hallucination, self-stabbings depersonalization/derealization, suicidal thoughts/actions, and cognitive disorders) and neurological (disturbed sleep patterns and nightmares, insomnia, tremors, seizures, hyperthermia, mydriasis, blurred vision, paresthesias, bruxism, motor automatisms, headache and dizziness) symptoms, these compounds could evoke sinus tachycardia, heart palpitations, chest pain, hypertension, S-T segmental changes, myocarditis, cardiac arrest, disseminated intravascular coagulation, disturbances in the acid-base balance and electrolyte balance, rabdomyolysis, acute kidney and liver failure, and fatal multiorgan failure. Potent agitation and aggressive behavior often pose a serious treat not only for a person being under the drugs influence but also to other people.

PROF. DSC JOLANTA B. ZAWILSKA PRESENT POSITION

Head, Department of Pharmacodynamics Medical University of d, d, Poland.

SCIENTIFIC INTERNSHIPS Biological Research Center Hungarian Academy of Sciences, Szeged, Hungary; Department of Pharmacology, Emory University School of Medicine, Atlanta, USA; Centre for Chronobiology, School of Biomedical and Molecular Sciences, University of Surrey, Guildford, United Kingdom; Institut des Neurosciences Cellulaires et Intgratives, Dpartment de Neurobiologie des Rythmes, Unit Mixte de Recherche 7168/LC2 Universit Louis PasteurCentre National de la Recherche Scientifique, Strasbourg, France. Expert in neuropsychopharmacology, neurochemistry and chronobiology.

RESEARCH FIELDS: (1) psychoactive substances with addictive potential, (2) molecular mechanisms of drugs actions, (3) receptors and signal transduction pathways, (4) biological rhythms and their role in physiology and pathology.

Author of 195 peer-reviewed publications. Member of Federation of the European Neuroscience Societies Schools Committee (2002-2004, 2008-2010), Committee of Neurobiology Polish Academy of Sciences (2007-2018), Committee of Physiology and Pharmacology Polish Academy of Sciences (2015-2018), Pharmacological Reports Editorial Board (2017-2021).

XII COPERNICAN INTERNATIONAL YOUNG SCIENTISTS CONFERENCE

13

aNaLyTICaL ChEMISTRy SECTIoN

oRaL pRESENTaTIoNS

ORAL PRESENTATION ANALYTICAL CHEMISTRY SECTION ORAL PRESENTATION

14

THE APPLICATION OF MODIFIED INTEGRATED SCREEN-PRINTED SENSOR FOR THE VOLTAMMETRIC DETERMINATION OF U(VI)

Katarzyna Domaska, Katarzyna Tyszczuk-Rotko, Agnieszka Szwagierek

Faculty of Chemistry, Department of Analytical Chemistry and Instrumental Analysis,

Maria Curie-Sklodowska University Keywords:voltammetry, screen-printed electrode, uranium, water analysis

Increasing environmental pollutionis a serious threat to human health. The development of industry, transport or agriculture contributes to release organic and inorganic pollutants to air and water. Especially, increasing contamination of heavy metals, which are hardly biodegradable and can get to the human body with food and water, may lead to serious human diseases. This phenomenon causes requirement for new analytical methods, which enable carrying out rapid, precise and cheap routine determination of heavy metal ions in environmental samples.One of the most desirable methods are those, which can be performed at the place where the sample is collected (field analysis). Then it is possible to control the concentration of pollutants and prevent long-scale environmental contamination.

Concentration of the uranium in environmental samples is generally low, but its usage for the production of nuclear energy and performanceof acquisition stages: uranium mining, milling, conversion and enrichment, lead to significant increasing its contamination. Exposure to uranium is harmful to health. It can accumulate in the kidneys and the skeleton andis toxic to the lungs, the liver and the brain. Therefore, it is desirable to control its contamination in environmental samples [1].

Voltammetry is an electrochemical method, which allow carrying out sensitive, precise and fast analysis of both organic substances and inorganic ions [2]. Integrated screen-printed electrodes (SPEs) used in voltammetry may be an alternative to the toxic hanging mercury drop electrode or commonly applied glassy carbon electrode. The integrated sensors based on screen-printed technology are promising tools for the trace determination of heavy metal ions due to their commercial availability, small size, good reproducibility and repeatability [3]. The screen-printed carbon electrode modified with lead was successfully involved for U(VI) determination.

The application of the integrated screen-printed carbon electrode plated in situ during differential pulse voltammetric measurements with lead film allowed to determine U(VI) in the presence of cupferron as a complexing agent at very low concentration level. Under optimized conditions a linear range of the calibration graph was from 1 10-10 to 1 10-8 mol L-1 for the accumulation time of U(VI)-cupferron complexes of 60 s. Very low limit of detection (LOD) 1.92 10-11 mol L-1and limit of quantification (LOQ) 6.40 10-11mol L-1was reached. The influence of the presence of surfactants in natural water samples was minimized by 30 s of sample shaking with 0.5 g of Amberlite XAD-7 resin. Bibliography: [1] E.S. Craft, A.W. Abu-Qare, M.M. Flaherty, M.C. Garofolo, H.L. Rincavage, M.B. Abou-Donia, Journal of

Toxicology and Environmental Health, Part B, 2004, 7, 297317. [2] A.N. Golikand, M. Asgari, M.G. Maragheh, E. Lohrasbi, Journal of Applied Electrochemistry, 2009, 39, 65-70. [3] O. Domnguez Renedo, M.A. Alonso-Lomillo, M.J. Arcos Martnez, Talanta, 2007, 73, 202-219.

COMPARISON OF MENAQUINONE DETERMINATION ON REFRESHABLE AMALGAM FILM MULTI-DISC ELECTRODE AND GLASSY CARBON BI-DISC ELECTRODE

Katarzyna Jedliska, Justyna Ubysz, Bogusaw Ba

Faculty of Materials Science and Ceramics, Department of Analytical Chemistry, AGH University of

Science and Technology, Krakw Keywords: menaquinone, stripping voltammety, voltammetric determination, renewable amalgam film electrode, glassy carbon electrode.

Menaquinone (MK, vitamin K2) is naturally occurring vitamer of liposoluble vitamin K, which

plays a crucial role in human health, especially in blood clotting process, cardiovascular health, cancer risk and bone health. MK is predominantly bacterially-synthesized form of vitamin K, which is mainly found in fermented foods as cheese, curd, and natto. In the present study a highly sensitive method for quantitative determination of menaquinone on two different types of home-made voltammetric working electrodes is presented.

An electrochemical sensor with the glassy carbon bi-disc electrode consist of two glassy carbon discs which are symmetrically arranged on the lateral surface of the guidewire, formed with chemically resistant resin. A core of the amalgam film multi-disc electrode [1] is based on similar construction [2], however herein the surface of the working electrode constitute six silver electrodes. Moreover an additional sensor body, filled with the 1 wt. % silver liquid amalgam drop, which enables simple and fast mechanical amalgam film refreshment before each measurement was used.

Both electrodes were successfully used in trace analysis of menaquinone under the optimized conditions with a conventional three-electrode system. The electrochemical behavior of MK electro-oxidation and reduction on glassy carbon as well as on amalgam film layer was investigated using cyclic voltammetry. The optimization of experimental conditions included selection of the appropriate supporting electrolyte solution, DP mode parameters and potential and time of preconcentration. The limit of detection, linear range, sensitivity, precision and accuracy for MK quantitative analysis on both electrodes were determined. Bibliography: [1] K. Jedliska, M. Strus, B. Ba, Electrochim. Acta, 2018, 265, 355-363. [2] B. Ba, S. Ba, Electrochem. Commun., 2010, 12, 816-819.

This work was supported by the Polish National Science Centre (Project No. 2015/19/B/ST5/01380).


15

APPLICATION OF LC-MS FOR THE ANALYSIS OF ANTISENSE OLIGONUCLEOTIDES OF THE FIRST AND SECOND GENERATION

Anna Kaczmarkiewicz, ukasz Nuckowski, Sylwia Studziska, Bogusaw Buszewski

Chair of Environmental Chemistry and Bioanalytics, Faculty of Chemistry, Nicolaus Copernicus

University in Toru Keywords: antisense oligonucleotides, mass spectrometry, liquid chromatography, ion pair reagents, alkylamines

Antisense oligonucleotides are components of nucleic acids, characterized by a modified structure. Structural modifications improve their stability in biological systems and affinity to bind with the sense strand of DNA or RNA. The most popular modifications are phosphorothioates. Currently, six antisense drugs are available on the market and are used in the treatment of several diseases, e.g. cancer or spinal muscular distrophy. However, many of these compounds are in various stages of clinical trials.

The use of oligonucleotides as therapeutic agents has enforced the need for identification and determination of these biomolecules as well as their metabolites in various types of matrices, e.g. serum, blood, tissues or urine samples. One of the most commonly used method in oligonucleotides analysis is ion pair reversed-phase liquid chromatography. Therefore, the principal aim of our experiment was to investigate the influence of the six different types of ion pair reagents and five various columns on the seven antisense oligonucleotides separation. The oligonucleotides with the same sequence, but the different modifications and length were selected. An important aspect was also to investigate the impact of the type of ion pair reagent on the mass spectrometry signal intensity of oligonucleotides. The alkylamine ensuring the highest mass spectrometry signal intensity was applied in the determination and separation of the mixture of seven oligonucleotides in serum samples. The use of gradient elution allowed to shorten the analysis time to 8 minutes. The limit of quantification of serum samples enriched with oligonucleotides was 0.23-0.56 M. The method was linear in the range of concentration from 0.23 M to 1.84 M.

Acknowledgements The authors are grateful to National Science Centre (Cracow, Poland) for financial support under Sonata Bis project (2016/22/E/ST4/00478).

DYNAMIC EXTRACTION OF AQUEOUS SAMPLES WITH NEEDLE TRAP DEVICE

Kamila Kdziora-Koch, Iwona Rykowska, Wiesaw Wasiak

Faculty of Chemistry, Department of Analytical Chemistry, Adam Mickiewicz University in Pozna Keywords: sample preparation, extraction, needle trap device, gas chromatography

The needle trap device (NTD) is one of the needle-based extraction techniques introduced in early 2000s for sample pretreatment before chromatographic analysis [1]. In this technique, a specially designed stainless steel needle is filled with an appropriate sorbent used as extraction phase. For extraction, the sample is drawn inside the needle through the sorbent layer. Afterwards, the adsorbed analytes are desorbed from extraction phase and subjected to chromatographic analysis [2].

According to sample state, different sampling methodologies have been applied. In the case of liquid samples, NTD has been rarely applied for dynamic extraction. This sampling methodology is relied on direct passing the liquid sample through the extraction system, consisted of a syringe and an extraction needle. The reason for this may be a flow restrictions produced by extraction phase [3]. Therefore, the choice of a sorbent material as well as proper preparation of extraction system is very important.

In this work, we took into consideration the possibility of using graphene in NTD as extraction phase for the dynamic extraction of aqueous samples. The extraction device was prepared in such a way that the extraction performance was high and no flow resistance was observed. The extraction procedure was as follows: conditioning of extraction phase, sampling, air passing, desorption, GC-MS analysis. After needle device preparation, the extraction efficiency of prepared device was evaluated via analysis of obtained eluates as well as aqueous fraction obtained after sample passage. The recoveries of analytes in eluates were in the range of 89 101 % and no analytes were detected in the aqueous fraction. Then, the NTD was subjected to optimization process. The performances of different sorbent materials packed in the needle trap device were also compared. Bibliography: [1] J. A. Koziel, M. Odziemkowski, and J. Pawliszyn, Anal. Chem., 2001, vol. 73, no. 1, pp. 4754. [2] K. Kdziora and W. Wasiak, J. Chromatogr. A, 2017, vol. 1505, pp. 117. [3] M. Pietrzyska and A. Voelkel, Talanta, 2014, vol. 129, pp. 392397.


16

DETERMINATION OF SELECTED AMINO ACIDS BY RP-HPLC AFTER DERIVATIZATION WITH 4-CHLORO-3,5-DINITROBENZOTRIFLUORIDE

Sylwia Kowalska, Aneta Jastrzbska, Emilia Maranowska, Marta Iskra, Edward Szyk

Faculty of Chemistry, Chair of Analytical Chemistry and Applied Spectroscopy, Nicolaus Copernicus

University in Toru

Keywords: amino acids, CNBF, derivatisation, high-performance liquid chromatography

Tryptophan, tyrosine, phenylalanine, glycine and glutamic acid are compounds which are responsible for producing of the neurotransmitters (serotonin, dopamine, noradrenaline, adrenaline and -aminobutyric acid) in the central nervous system. For this reason these amino acids must be supplied with food to maintain normal homeostasis of the organism.

High-performance liquid chromatography (HPLC) witch UV-Vis detection is most used for determination the discussed amino acids.However, their similar chemical structure and lack of strong chromophore groups force their derivatization before analysis. The analysis of amino acids in the food samples by HPLC after a preliminary derivatization with diethyl ethoxymethylenemalonate (DEEMM) [1], phenyl isothiocyanate (PITC) [2], ophthalaldehyde (OPA) [3] was described. Unfortunately, the derivatization reaction reveals some inconveniences: unstable derivatives (OPA), a time of derivatisation reaction, removal of an excess of the reagent after the derivatisation (PITC) and a low level of sensitivity (DEEMM).

The main objective of the study was developing a procedure of tryptophan, tyrosine, phenylalanine, glycine and glutamic acid derivativessynthesis. We proposed chromatographic determination of amino acids after precolumn derivatisation with 4-chloro-3,5-dinitrobenzotrifluoride (CNBF). The CNBF derivatization are rapid at moderate temperature, along with the resultant derivatives being very stable and of high ultraviolet and fluorescent absorption [4]. Shi, et.al. [5] applied this reagent for determination of free amino acids (aspartic acid, glutamic acid, asparagine, histidine, glutamine, arginine, serine, threonine, proline, glycine, alanine, valine, methionine, cysteine, tryptophan, leucine, isoleucine, phenylalanine, tyrosine, lysine) in Asparagus Tin.

In the present work we optimized conditions of derivatives synthesis and chromatographic analysis. The precolumn derivatisation conditions, including the CNBF concentration, reaction pH, temperature and reaction time were tested. Moreover, chromatographic separation parameters (type and concentration of eluent, conditions of chromatographic separations) were selected.

The proposed method was applied to the determination of amino acids in different food samples. The liquid samples were degassed in the ultrasonic bath, whereas the solid products were extracted. The obtained results were subjected to statistical analysis.

Bibliography: [1] B. Redruello, V. Ladero, B. del Rio, M. Fernndez, M.C. Martin, M.A. Alvarez, Food Chemistry, 217 (2017), 117

124. [2] R. Domnguez-Perlesa, N. Machadoa, A.S. Abraoa, V. Carnidea, L. Ferreirab, M. Rodrigues, E. A.D.S. Rosaa,

A.I.R.N.A. Barrosa, Journal of Food Composition and Analysis, 53 (2016), 6976. [3] Y. Zhu, Y. Luo, P. Wang, M. Zhao, L. Li, X. Hua, F. Chen, Food Chemistry, 194 (2016), 643649. [4] A.M. Piasta, A. Jastrzbska, M.P. Krzemiski, T.M. Muzio, E. Szyk, Analytica Chimica Acta, 834 (2014), 5866. [5] T. Shi, T. Tang, K. Qian, F. Wang, J. Li, Y. Cao, Analytica Chimica Acta, 654 (2009), 154161.

INFLUENCE OF SURFACTANTS ON THE ADSORPTION AND STABILITY OF THE CARRAGEENAN/ALUMINA SYSTEM

Jakub Matusiak, Elbieta Grzdka

Faculty of Chemistry, Department of Radiochemistry and Colloid Chemistry, Maria Curie-

Skodowska University in Lublin Keywords: adsorption, polysaccharide, stability, metal oxide

Adsorption of different molecules onto metal oxides has been in the interest of many scientists for years. A lot of the already existing formulations contain polymers and surfactants, which make the description of the adsorption process much harder. Current trend in the science and industry is to use novel and eco-friendly materials. This is why, the use of different natural polymers such as polysaccharides and polyamino acids is getting a lot of attention these years [1, 2]. Full description of the adsorption process is particularly important to characterize stability of metal oxide suspensions. The addition of polysaccharides and surfactants influences the stability of such systems [3]. Different scenarios can be distinguished in case of stability of the metal oxide suspensions. These are steric, electrosteric and depletion stabilization. If the polymer or surfactant does not adsorb on the solid surface, depletion stabilization may occur. This type of stabilization is connected with the presence of non-adsorbed molecules between solid particles. Such situation may cause the repulsion between them. However, if the polymer adsorbs on the solid surface, steric or electrosteric stabilization occurs [4].

The aim of this study was to investigate the adsorption and stability in the carrageenan/alumina system. To determine the adsorption of carrageenan on the Al2O3 surface, colorimetric method proposed by Albalasmeh et. al. was used [5]. Influence of different ionic surfactants (silicon surfactant Silube J2, fluorinated surfactant S-106a and hydrocarbon surfactant MTAB) on the adsorption of carrageenan was also investigated. Moreover, the influence of pH on the adsorption process was also studied. In case of stability, the influence of the polymer concentration, as well as the presence of mentioned surfactants were investigated. Obtained results shows that carrageenan adsorbs on the alumina surface, and the addition of surfactants increases the adsorption of the used polysaccharide. This is probably due to the formation of the multilayer polymer-surfactant complexes, which have higher affinity towards the solid surface than pure polymer. The stability measurements indicate, that the concentration of carrageenan as well as the addition of surfactants both increase stability of the alumina suspension. In this case, the possible stabilization mechanism is electrosteric and depletion stabilization. Bibliography: [1] E. Grzdka, J. Matusiak, Carbohydrate Polymers, 2017, 175, 192-198. [2] I. Ostolska, M. Winiewska, RSC Advances, 2015, 5(36), 28505-28514. [3] P. Somasundaran et al., Colloids and Surfaces A: Physicochemical and Engineering Aspects, 1998, 133, 125-133. [4] J. Matusiak, E. Grzdka, Annales Universitatis Mariae Curie-Skodowska Sectio AA, 2017, 72, 33-45. [5] AA. Albalasmeh, AA. Berhe, TA. Ghezzehei, Carbohydrate Polymers, 2013, 97(2), 253-261.


17

DEVELOPMENT OF ANTISENSE OLIGONUCLEOTIDES SOLID PHASE EXTRACTION METHOD

ukasz Nuckowski, Anna Kaczmarkiewicz, Sylwia Studziska, Bogusaw Buszewski

Chair of Environmental Chemistry and Bioanalytics, Faculty of Chemistry Nicolaus Copernicus

University in Toru Keywords: antisense oligonucleotides, sample preparation, solid-phase extraction, liquid chromatography

Short, usually build of 10-25 nucleotides, sections of DNA or RNA, called antisense oligonucleotides (AS-OGNs), can bind with sense RNA strand by Watson-Crick base pairing. It effect in inhibition of transcription and translation and allows, among others, for control of pathogens proteins synthesis. However, classical phosphodiester OGNs prove to be ineffective due to fast degradation by the intracellular endonucleases and exonucleases. Their chemical modification allow for their successful use as medicines. Increasing number of OGNs is in various stage of clinical trials in many fields, such a cardiovascular disease, respiratory problems (e.g., asthma), inflammatory problems (e.g., Crohns Disease), infectious diseases (e.g., HIV)and almost half of it in as anticancer therapies.

Medical application of OGNs in antisense therapy stay in connection with necessity of their determination but also identification of their metabolites in complex biological matrices. Before high-performance liquid chromatography analysis, the most important technique in OGNs analysis nowadays, exceptional techniques are required to remove interfering compounds, especially proteins strongly biding to OGN. For this purpose commonly used are: protein precipitation, enzyme digestion and liquid-liquid extraction. Solid phase extraction is also popular technique, but there are weak data describes the impact different SPE parameters on extraction efficiency.

In this study, the impact of various parameters on extraction efficiency of phosphorothioate ONGs before analysis by ultra-high performance liquid chromatography with UV detection was investigated. Two SPE columns were tested for this purpose: polymeric Oasis HLB and silica based octadecyl InerSep C18. The ion-pair mode was used in the extraction and as an ion-pair reagent (IPR) mixture of amine and 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) was used. Three amines were studied: hexylamine (HA), N,N-dimethylbutylamine (DMBA) and N,N-diisopropylethylamine (DIPEA). The effect of amine type, its concentration in IPR in elution solvent and during whole procedure, ion-pair formation time and methanol percentage in elution solution for extraction recovery was studied. Such a complex study was performed for the first time for the extraction of AS OGNs by SPE. The best recovery for 20-mer phosphorothioate oligonucleotide (PS) was obtained by using 5 mM DMBA/150 mM HFIP as an IPR and 10/90% v/v IPR/methanol mixture as a elution solvent and was equal 101.41.8%. The same method applied for mixture of PS and its two synthetic metabolites (19-mer M1 and 18-mer M2) gives recoveries equal 79.80.4%, 80.11.7%, 79.00.3% respectively. The developed SPE method preceded by LLE with phenol/chloroform/isoamyl alcohol reagent for protein removing was used to extract phosphorothioate OGN and its metabolites from enriched human plasma. The recoveries for each of studied compounds were as follows: PS 79.24.7%, M1 80.36.2%, M2 81.23.4%.

Financial support was provided by the National Science Centre (Cracow, Poland) under Sonata Bis project (2016/22/E/ST4/00478).

INFLUENCE OF THE WAY OF GLUCOSE OXIDASE IMMOBILIZATION ON ITS ACTIVITY TOWARDS GLUCOSE

Jakub P. Sk1, Edyta Matysiak-Brynda1, Artur Kasprzak2, Magdalena Poplawska2,

Mikolaj Donten1, Anna M. Nowicka1

1Faculty of Chemistry, Department of Inorganic and Analytical Chemistry, University of Warsaw 2Faculty of Chemistry, Department of Organic Chemistry, Warsaw University of Technology

Keywords: reduced graphene oxide doped with ferrocene, glucose oxidase, oxidation, morphological properties

Performing of the metabolic function by the humans body cells require an energy. Glucose is a

small, simple sugar that serves as a primary fuel for energy production, especially for the brain, muscles and several other body organs and tissues. Glucose also serves an a building block for structural molecules glycoproteins or glycolipids. The normal level of glucose in blood is at the level from 4.4 to 6.6 mM. Abnormally high or low levels result in a serious, potentially life-threatening complications. It is especially important for diabetic patients because in this case it can end with death. Nowadays, there are a lot of various analytical method, which can be used for determination of glucose concentration in the real samples eg. electrophoresis, HPLC, colorimetric measurements, ICP-MS and voltammetric methods [1-3]. Among them, the electrochemical methods have more attention because of their fast response time, high sensitivity and simple equipment.Due to high sensitivity and selectivity, enzymatic methods for this sugar detection are the most popular. Generally, such sensors devices rely on the catalytic activity of enzymes such as glucose oxidase (GOx) or glucose dehydrogenase (GDH) to oxidase glucose.

The way of enzyme immobilization on the electrode surface has a significant effect on the amount of the immobilized enzyme and in consequence on its activity. Herein, we present the amperometric glucose biosensor based on two sensing platforms for glucose oxidase immobilization: GC/RGO-Fc and GC/RGO-Fc(COOH)2. The morphology of obtained sensing platforms were characterized by scanning electron microscopy, Raman spectroscopy and quartz crystal microbalance with dissipation. GOx was immobilized onto the modified electrode surfaces by two different ways in case of RGO-Fc using glutaraldehyde as a crosslinking agent. For RGO-Fc-(COOH)2 platform the enzyme was anchored by formation of amide bonds between carboxylic groups of platform and amino groups presented in enzymes structure. Amperometric response was measured as a function of concentration of glucose in the solution at a potential +0.35V (vs. Ag/AgCl) in PBS buffer at pH 7.0. The catalytic current response was highly sensitive and revealed a linear increasing with increasing concentration up to 10mM. The detection limit was ca. 5M and 0.3M for RGO-Fc and RGO-Fc-(COOH)2, respectively. Obtained results clearly showed that the ferrocene moieties present in the immobilization matrix of GOx play the role of mediator in the electron transfer between the redox center of glucose oxidase and the electrode surface. The constructed sensors can be used in the determination of glucose in the real samples. Bibliography: [1] A.L. Galant, R.C. Kaufman, J.D. Wilson, Food Chemistry, 2015, 188, 149-160. [2] Z. Huang, J. Yang, L. Zhang, X.Geng, J. Ge, Y. Hu, Z. Li, Anal. Methods, 2017, 9, 4275-4281.

[3] X. Zhang , Q. Liao, M. Chu, S. Liu, Y. Zhang, Biosnes. Bioelectron,2016, 52, 281-287.

This work was supported by the National Science Centre Poland, Grant No. 2014/15/D/ST4/02989.


18

THE LIPID NANOPARTICLES (NLC AND SLN) AS NATURAL PENETRATION PROMOTERS OF TRANS-EPIDERMAL PENETRATION

Elbieta Szczepaska, Beata Grobelna

Faculty of Chemistry, Department of Analytical Chemistry,

Laboratory of Chemistry and Analytics of Cosmetics, University of Gdask Keywords: lipid nanoparticles, promoters, trans-epidermal penetration

Currently, one of the most interesting issues for cosmetologists is the penetration of active substances through the skin. Especially epidermal part, due to the high lipophilicity part corneum is a barrier for many substances. Most cosmetic products act on the surface layers of the skin, not reaching its living layers. As a result of many years of research, we have managed to develop a method that allows transport of valuable ingredients to the deeper layers of the skin. Nanotechnology provides such possibilities.

SLNs are spherical particles made of solid lipids at room temperature, dissolved in the aqueous phase with the addition of an emulsifier. The SLN forming lipids are triglycerides (tristearate, tripalmitate), some glycerides, e.g. glyceryl monostearate, saturated fatty acids (stearic, palmitic, steroids (cholesterol) and waxes (cetyl palmitate).

In contrast, NLC is an alternative to SLN, solving problems related to it. They are composed of a mixture of solid lipids and oils. This composition brings many benefits, among others: lowering the melting point and increasing the amount of active substance dissolved in the lipid mixture.

It should be emphasized that lipid nanoparticles (both SLN and NLC) provide a high percentage of encapsulation, better protection of active substances incorporated and allow control of the release of these substances. Their additional advantage is the use of natural, safe components for the synthesis, which is an alternative in the use of nanoparticles obtained by chemical means [1,2].

Therefore, the aim of the research was the synthesis of lipid nanoparticles, both NLC and SLN. This nanoparticles thus obtained will be a potential capsule for encapsulating various active substances in them.

As a method of obtaining lipid nanoparticles, a microemulsion technique was selected, during which lipids are melted and mixed with a hot solution of surfactant. The second step was to disperse the formed microemulsion in a large amount of water. The size and shape of the obtained nanoparticles was characterized by transmission electron microscopy (TEM). Bibliography: [1] Poovi Ganesan, Damodharan Narayanasamy, Sustainable Chemistry and Pharmacy, 2017, 6, 37-56. [2] Magorzata Geszke-Moritz, Micha Moritz, Materials Science and Engineering: C, 2016, 68, 982-994.

This study was financed by the University of Gdansk within the project supporting young scientists and PhD students (grant No. BMN 538-8210-B797-17).

APPLICATION OF NEW ELECTROCHEMICAL SENSORS COATED WITH CARBON NANOFIBERS IN THE DETERMINATION OF PARACETAMOL

Agnieszka Szwagierek, Katarzyna Tyszczuk-Rotko, Katarzyna Domaska

Faculty of Chemistry, Department of Analytical Chemistry and Instrumental Analysis,

Maria Curie-Skodowska University Keywords:voltammetry, carbon nanofibers, paracetamol

Remains of pharmaceutical preparations get into the environment as a result of their production in manufacturing factories. An additional source of contamination are expired preparations thrown directly into the environment without proper disposal. These substances come from wastewater and hospital wastes and from every household. The presence of pharmaceutical preparations in the environment is a serious problem and a major challenge for water and wastewater treatment technologies. Many substances are not decomposed and eliminated in the wastewater treatment process in the treatment plant. One of the most-bought pharmaceutical preparations without a prescription is paracetamol.

Paracetamol is an analgesic and antipyretic drug used worldwide. It has a weak anti-inflammatory effect and does not interfere with the blood coagulation process. It is used in children and adults during colds and fevers and in relieving muscle pains, joints, bones, back pain, headache, menstrual pain, cancer and post-operative pain. Paracetamol can be used alone or in combination with non-steroidal anti-inflammatory drugs (eg acetylsalicylic acid, ketoprofen, ibuprofen, diclofenac, naproxen) or with opioid analgesics for the treatment of severe pain. In addition, paracetamol is characterized by low risk of side effects and does not damage the gastric and intestinal mucosa. However, when used in high doses over a long period of time, it can lead to kidney failure and toxic damage to hepatocytes and, as a consequence, liver damage.

The paper presents a new voltammetric method for the determination of paracetamol in natural water samples using a composite screen printed electrode. On the surface of the miniature sensor there are three electrodes: working (screen printed carbon electrode covered with carbon nanofibers), auxiliary electrode (platinum) and reference electrode (carbon). The basic electrolyte is 0.1 mol L-1 H2SO4. The presented procedure is simple and fast, because the commercially available sensor does not require additional modifications. There was no influence of metal ions and organic substances found in natural waters on the analytical signal of paracetamol. The proposed method allows to obtain a linear paracetamol calibration curve in the concentration range from 2 10-9 to 2 10-7 mol L-1 and the limit of detection at 4.76 10-10 mol L-1. The method has been successfully used for the determination of paracetamol in aquatic ecosystems.

ORAL PRESENTATION ANALYTICAL CHEMISTRY SECTIONORAL PRESENTATION

19

VOLTAMMETRIC METHOD FOR THE DETERMINATION OF B VITAMINS

Justyna Ubysz, Katarzyna Jedliska, Radosaw Porada, Bogusaw Ba

Faculty of Materials Science and Ceramics, Department of Analytical Chemistry, AGH University of Science and Technology

Keywords: stripping voltammetry, riboflavin, cobalamin, thiamine

Vitamins are organic compounds and an essential nutrients that human body needs in small amounts to work properly. Due to their solubility, they are divided into fat-soluble vitamins (vitamins A, D, E and K) and soluble in water (vitamins B and C). Vitamin B1 (Thiamine) is a heterocyclic chemical compound composed of thiazole and pyrimidine rings connected by a methine bridge. It performs important biochemical functions as a coenzyme thiamin pyrophosphate (TPP) which is involved in energy metabolism [1].

Vitamin B2 (Riboflavin) is the composition of coenzyme and involved in carbohydrate, protein and fat metabolism. It has a beneficial effect on the condition of the skin, nails and hair [2].

Vitamin B12 (Cobalamin) is a water-soluble vitamin that participates in production of red and white cells. It also supports the functioning of nerve cells and replication of DNA and RNA [3].

Due to the electroactivity of vitamins B1, B2, B12 stripping voltammetry can be used for them highly sensitive determination in the presence of an organic matrix, after deoxidizing the solution.

This work discusses the results of research on the possibility of vitamins B determination in dietary supplements using a mercury electrode with controlled drop growth (CGMDE) by differential impulse voltammetry (DPV). Preliminary research included optimization of the composition, concentration and pH of the basic electrolyte and instrumental parameters of stripping cyclic voltamograms (DP ASV and DP CSV). Bibliography: [1] Pradeep Kumar Brahman,Sensors and Actuators B, 177 (2013), 807 812. [2] Tao Nie, Synthetic Metals, 189 (2014), 161172. [3] Mamas I. Prodromidis, Electroanalysis, 27 (2015), 1876 1882.

HUMIC ACIDS SORPTION FROM WATER USING ZIRCONIUM DIOXIDE NANOPARTICLES

Katarzyna Willkosz, Ewa Niewiara, ukasz Magda

AGH University of Science and Technology, Faculty of Material Science and Ceramics, Department

of Analytical Chemistry, Cracow, Poland

Keywords: humic acids, zirconium dioxide, nanomaterials Humic acids are a common component of natural waters. Humic compounds can affect

unprofitably in organoleptic properties of groundwater intended for humans consumption, so their presence is not desirable. Futhermore humic acids may adsorb some toxic compounds e.g. heavy metals. This fact indicates the need to purify water from humic compounds. The aim of this work was to show sorption efficiency of humic acids using nanopowders based on zirconium dioxide as a sorbent.

For this purpose nanopowders based on zirconium dioxide were used as a sorbent for testing sorption effeciency of humic acids. Tested sorbents were synthesized by ammonia method and modified by elements of the lanthanide group. Neodymium were used as a modifier for zirconium dioxide nanoparticles in an amount of 0.5 and 1.0%. Sorption processes were carried out in acidic, alkaline enviroment and in pH corresponding to the isoelectric point of nanopowder suspension. The effect of time sorption on sorption efficiency was also examined.

For all tested nanopowders sorption efficiency of humic acids has the greatest value at pH 5.0. Addition of modifier - neodymium cause the improvement of adsorption efficiency in alkaline environment and atpH value corresponding to the isoelectric point of nanopowder suspension. The optimal time of sorption for all tested nanopowders is about 30 minutes. Sorption process of humic acids for unmodified nanopowder based on zirconium dioxide is more stable in time than for modified nanopowders.

Summarizingthe obtained results there is a possibility to apply nanopowders based on zirconium dioxide as sorbent for natural components of water such as humic acids.

This study was carried out within the AGH University of Science and Technology (Cracow) - grant number 15.11.160.017.

ORAL PRESENTATION ANALYTICAL CHEMISTRY SECTIONORAL PRESENTATION

20

NEW METHODS OF INTERPRETATION AND VISUALIZATION OF MULTI DIMENSIONAL DATA

Justyna Zuziak, Magorzata Jakubowska

AGH University of Science and Technology, Faculty of Materials Science and Ceramics, Department

of Analytical Chemistry, Cracow Keywords: chemometry, voltammetry, multivariate data visualization and analysis, Chernoff faces, star plots, Kohonens network

The huge amount of obtained results may provide many difficulties with their interpretation and presentation in interesting way.Chemometric methods are helpful tools for an objective and comprehensive interpretation of results obtained by various measuring techniques.Chemometry as an interdisciplinary field from the borderline of computer science, mathematics, chemistry and other technical fields deals with extracting useful information from multidimensional measurement data.These tools are particularly useful in assessing a large amount of data that would take many hours to interpret in a standard way. The use of modern chemometric techniques significantly shortens this time, visualizes the presented phenomena and quickly provides relevant information.The range of applications and the number of chemometric methods is increasing from year to year, and reports in the world literature indicate that many problems can be effectively solved using only chemometric analysis techniques from the moment of planning the experiment to the final stage of experimental data development.

Electrochemical experiments were carried out in a three electrode quartz cell with a multipurpose electrochemical analyzer 8KCA. Voltammetric signals were registered from black, green, red and white tea infusions of China and Vietnam origin. The composition of the supporting electrolyte was 0.03 M sodium hydroxide. All experiments were carried out using 3 independentsamples (without special preparation) of 8 tea species and for each sample recording was done in triplicate. 72 voltamperometric curves were obtained, which were interpreted using the latest chemometric techniques.Insight to the experimental data and extraction of the useful information were done applying Chernoff faces, star plots, radar plot, matrix scatterplot, polar dendrogram, Kohonens network and Principal Component Analysis.

The tools used provided a lot of interesting information. We managed to divide the received samples depending on the type and country from which they came.It proves that graphical presentation by diagrams and charts has a number of advantages in comparison to analysis of the measured signals or numerical datasheets. The same data presented and modeled by different methods may deliver various, complementary conclusions and also the strategy verifies the quality of the experiments. Bibliography: [1] J. Zuziak, G.Moskal, M.Jakubowska,, Journal of Electroanalytical Chemistry, 2017, 806, 97-106.

Acknowledgments This work was supported by AGH University of Science and Technology, Poland (Project No. 18.18.160.766).

XII COPERNICAN INTERNATIONAL YOUNG SCIENTISTS CONFERENCE

21

ChEMICaL TEChNoLogy &

oRgaNIC ChEMISTRySECTIoN

oRaL pRESENTaTIoNS

ORAL PRESENTATION CHEMICAL TECHNOLOGY & ORGANIC CHEMISTRY SECTIONORAL PRESENTATION

22

REVERSIBLE DEACTIVATION RADICAL POLYMERIZATION IN MINIEMULSION

Paulina Biedka, Pawe Chmielarz

Department of Physical Chemistry, Rzeszow University of Technology, Poland Keywords: RDRP, ARGET ATRP, miniemulsion, butyl acrylate

In reversible-deactivation radical polymerization (RDRP) methods radicals are reversibly regenerated, what enables well control over reaction kinetics and receiving polymers with determined architecture [1]. The most important RDRP technique is atom transfer radical polymerization (ATRP), particularly approach with low catalyst concentration, such as activator regenerated by electron transfer (ARGET) ATRP [2]. This method provides well-defined polymers with predetermined molecular weights (MWs), narrow molecular weight distributions (MWDs).

Reactions carried in heterogeneous media are facile way to reduce organic waste, simplify heat transport and decrease cost of solvents. Miniemulsion is configuration in which two immiscible phases coexist and one is suspended in other one [3].

These study focuses on poly(butyl acrylate) synthesis in miniemulsion, with the use of ARGET ATRP. During these research a few optimizations has been done, including decrease of surfactant and reducing agent (RA) content, costabilizer elimination and reduction of reaction time.

Materials: Butyl acrylate, sodium dodecyl sulfate, ethyl -bromoisobutyrate, NaBr, CuIIBr2 and -D-glucose were purchased from Sigma Aldrich. 2-Hydroxyethyl-2-methyl-2-bromopropionate (HO-EBiB) and tripicolylamine (TPMA) were synthesized according to ref. [4,5], respectively.

Synthesis: Poly(butyl acrylate) was synthesized via ARGET ATRP, with the use of glucose as RA and two different initiators.

The first-order kinetic relationship of analyzed synthesis, confirmed controlled character of polymerization. Application of HO-EBiB as initiator decreased reaction rate, comparing to reactions with EBiB as initiator. Optimizations enabled decreasing of RA, surfactant and catalyst amount, and reducing time of reaction. Reaction conditions, MWsand MWDs are presented in tab. 1.

Table 1.Chosen reaction polymerization of poly(butyl acrylate) with the use of ARGET ATRP technique.

No.

Time [h]

Initiator [M]/[I]/[CuIIBr2]/(TPMA)]

DP* Mn,th ** kpapp***

[h-1] Mw/Mn

**** 1 2 HO-

EBiB 200/1/0.18/0.36 30.0 4060 0.31 1.74

2 2 EBiB 200/1/0.18/0.36 38.6 5140 0.26 1.82

* DP = [M]/[I], ** Mn, th = DP conversion Mmonomer + Minitiator, ***kpapp the slope of the ln([M]0/[M]) vs time plot, **** MWDs from GPC analysis.

In each ARGET ATRP processes, reactions with relatively high polymerization rates (kp

app in the range of 0.26 0.31) were observed. However received in this way polymers had broad MWDs (1.74 1.82). Therefore, further research will focus on optimization of ARGET ATRP process in miniemulsion conditions, mainly on narrow MWDs of received polymers.

Bibliography: [1] Matyjaszewski K., Macromolecules, 2012. 45: 4015. [2] Wang Y., et. al., Macromolecules, 2017. 50: 8417. [3] Zetterlund P.B., et al., Chemical Reviews, 2015. 115: 9745. [4] Krol P., et. al., Express Polym Lett, 2013. 7: 249. [5] Canary J.W., et al., Inorg. Synth., 1998. 32, 70.

THE APPLICATION ASPECT OF SILANES MONOLAYERS DEPOSITED ON DLC AND SI-DLC COATINGS

Ewelina Bystrzycka, Milena Prowizor, Micha Cichomski

Faculty of Chemistry, Department of Materials Technology and Chemistry, University of Lodz

Keywords: diamond-like carbon coatings, modification, wettability, tribology

Surface modification is an effective way to improve the properties of materials used in technology, industry and medicine. It influences on the efficiency of work of machines and devices. One of the more attractive materials used in these fields are diamond-like coatings (DLC). These coatings have unique properties and are a excellent material for chemical modification. They are characterized by an amorphous structure due to the presence of sp3 and sp2 carbon hybridization and have unique mechanical and tribological properties. Therefore, DLC are mainly used as coverings of e.g. mechanical elements and implants.

In order to demonstrate that it is possible to improve the properties of diamond-like coatings, the effect of incorporation of silicon into DLC matrix is presented in this paper [1]. The DLC coatings and silicon-incorporated coatings (Si-DLC) obtained using by mixture of methane and tetramethylsilane flows (CH4 and Si(CH3)4 ) in RF PACVD method were analyzed by contact angle measurements and tribological tests [2]. Then DLC and Si-DLC coatings were subjected to chemical modification using two silane compounds with different length of alkyl chain (1H, 1H, 2H, 2H- perfluorodecyltrichlorosilane - FDTS and 3,3,3-trifluropropyltrichlorosilane FPTS). It was presented that the modification by fluorosilanes leads to obtain the hydrophobic surfaces. It was also performed that obtained structures give the DLC and Si-DLC coatings greater possibilities due to improved tribological properties. Moreover, high durability of the produced layers in acids, alkalis and saline salts solutions, as well as on ultraviolet radiation was confirmed. The conducted research proved that silicon incorporation in DLC surface and formation of stable structures obtained by modification improve their properties and increase application possibilities.

Bibliography: [1] A. Jedrzejczak, D. Batory, M. Dominik, M. Smietana, M. Cichomski, W. Szymanski, E. Bystrzycka, M. Prowizor, W.

Kozlowski, M. Dudek, Surface & Coatings Technology, 2017, 329, 212-217. [2] E. Bystrzycka, M. Prowizor, I. Piwoski, A. Kisielewska, D. Batory, A. Jedrzejczak, M. Dudek, W. Kozlowski, M.

Cichomski, Materials Research Express, 2018, 036411.

Research financed from the National Science Center as part of the project No. 2014/13 / B / ST8 / 03114.

ORAL PRESENTATION

HIGH PRESSURE OR CONNOVEL, GREEN METHODS

Andrzej Dzienia1,2, Magdalena Tarnacka

1 Institute of Chemistry, University of Silesia, Katowice, Poland2 Silesian Center for Education and Interdisciplinary Research, University of Silesia, Chorzow, Poland

3

Keywords:high-pressure, confinement

Aliphatic polyesters i.e. poly

choice to reduce environmental pollution, moreover from renewable resourcesthe highly toxic catalysts based on a polyesters in medicine, mention that finding of an polymerizationof -caprolactone, resulting in products characterized by high molecular weight narrow distributions,

However, it should be stressed that was well demonstrated that to control polymerization of liquids [2]. Herein we show that conditions (temperature and pressure) and moderate molecular weights (Mnecessity of using complex and toxthe application of constrainingpressure [3]. The alumina membranes used as nanoreactors are an effective catalyst, which operate accordingly to the coordinationcharacterized by pretty high MInterestingly in nanotemplatespressureconditions.

Bibliography: [1] A. Dzienia, P. Maksym, M. Tarnacka, I. Grudzka

2017, 1823, 214. [2] P. Maksym, M. Tarnacka, A. Dzienia, K. Erfurt, A. Brzczek

Paluch, Polymer, 2017, 1823, 2[3] M. Tarnacka, A. Dzienia, P. Maksym, A. Talik, A. Ziba, R. Bielas, K. Kaminski, M. Pal

Macromolecules).

Authors are thankful for the financial support from the Polish National Science Centre within SONATA BIS 5 project (Dec 2015/18/E/ST4/00320).

High pressure polymerization of

PRESENTATION

HIGH PRESSURE OR CONFINEMENT IN NANOPOROUS ALUMINA MEMBRANESNOVEL, GREEN METHODS FOR PRODUCTION OF WE

VIA RING OPENING POLYMERIZATION

, Magdalena Tarnacka2,3, Agnieszka, Talik2,3, Kamil Kamiski

Institute of Chemistry, University of Silesia, Katowice, PolandSilesian Center for Education and Interdisciplinary Research, University of Silesia, Chorzow, Poland

3 Institute of Physics, University of Silesia, Chorzow, Poland

pressure, confinement, nanoporous, ring opening polymerization

Aliphatic polyesters i.e. polycaprolactone due to short biodegradation time seems to be choice to reduce environmental pollution, moreover many of monomers used to ROP

resources. Unfortunately, the main method of polyesters synthesis relies on the use of the highly toxic catalysts based on a heavy-metalscomplexes, therefore the polyesters in medicine, pharmacy and electronic industry seems to be strongly limited. It is worth to

finding of an efficient, inexpensive and ecologicalcaprolactone, resulting in products characterized by high molecular weight , is still a challenging task.

However, it should be stressed that recently significant progress in this matter has been reached. It well demonstrated that the application of high pressure can be a very efficient and promising way

to control polymerization of -caprolactone [1] as well as other monomers e.g. polymerizable ionic Herein we show that the proper combination of

conditions (temperature and pressure) and ii) concentration of water allows moderate molecular weights (Mn=1.6-19.0 kg/mol) and dispersitiesnecessity of using complex and toxic catalytic systems[1]. Even better

constraining geometries generated for example by alumina templates]. The alumina membranes used as nanoreactors are an effective catalyst, which

operate accordingly to the coordination-insertion mechanism resulting in nanowires of PCL characterized by pretty high Mn up to 53.5 kg/mol and moderate dispersions (=1.27

nanotemplates polymerization is significantly faster

A. Dzienia, P. Maksym, M. Tarnacka, I. Grudzka-Flak, S. Golba, A. Ziba, K. Kaminski, M. Paluch,

P. Maksym, M. Tarnacka, A. Dzienia, K. Erfurt, A. Brzczek-Szafran, A. Chrobok, A. Ziba, K. Kaminski, M. Paluch, Polymer, 2017, 1823, 214. Polymer, 2018, 140, 158-166. M. Tarnacka, A. Dzienia, P. Maksym, A. Talik, A. Ziba, R. Bielas, K. Kaminski, M. Pal

are thankful for the financial support from the Polish National Science Centre within SONATA BIS 5 project (Dec

High pressure polymerization of -caprolactone

CHEMICAL

23

US ALUMINA MEMBRANES AS A FOR PRODUCTION OF WELL-DEFINED POLYESTERS

YMERIZATION

, Kamil Kamiski2,3,Marian Paluch2,3

Institute of Chemistry, University of Silesia, Katowice, Poland Silesian Center for Education and Interdisciplinary Research, University of Silesia, Chorzow, Poland

Institute of Physics, University of Silesia, Chorzow, Poland

nanoporous, ring opening polymerization, polycaprolactone

due to short biodegradation time seems to be the perfect monomers used to ROP can be produced

method of polyesters synthesis relies on the use of , therefore the application of so produced

industry seems to be strongly limited. It is worth to , inexpensive and ecological-friendlymethod for ROP

caprolactone, resulting in products characterized by high molecular weight and

significant progress in this matter has been reached. It high pressure can be a very efficient and promising way

caprolactone [1] as well as other monomers e.g. polymerizable ionic combination of two parameters: i) thermodynamic

concentration of water allows to obtain polymers of dispersities (=1.07-1.50) without the

Even better effects can be also achieved by geometries generated for example by alumina templates at ambient

]. The alumina membranes used as nanoreactors are an effective catalyst, which might insertion mechanism resulting in nanowires of PCL

up to 53.5 kg/mol and moderate dispersions (=1.27-1.41). polymerization is significantly faster with respect to the high-

Flak, S. Golba, A. Ziba, K. Kaminski, M. Paluch, Green Chem.,

Szafran, A. Chrobok, A. Ziba, K. Kaminski, M.

M. Tarnacka, A. Dzienia, P. Maksym, A. Talik, A. Ziba, R. Bielas, K. Kaminski, M. Paluch, (Submitted to

are thankful for the financial support from the Polish National Science Centre within SONATA BIS 5 project (Dec

Keywords:

Generated from appropriate salt NHC effect on the polarity reverse of carbonyl compound. This umpolungcarbon atom is transformed into synthetNHCRonald Breslow in 1958 for thiamine in vivodecarboxylation of pyruvic acid. Named in his honor reaction intermediate is common acyl anion synthon which partimolecorganocatalysed reactions. It can be oxidized to acylesterification reactions and annulation reactions of ,

addition of enamine to acylannulation6reagents to obtain bicyclic lactams with unprotected NHthe applicability of widely kour team.[4

ring for many different Moreover, products were obtained with very high yields and purities. Bibliography[1][2][3][4][5][6]

This work was financially supported by National Science Centre grant SONATA BIS (UMO

SEM images of PCL nanowires produced at alumina membranes

CHEMICAL TECHNOLOGY & ORGANIC

NOVEL CARBENE-CATALYSED ANNULATIONREARRANGEMENT

Krzysztof Dzieszkowski

Faculty of Chemistry, Chair of Organic Keywords: N-heterocyclic carbenes, organocatalysis, aza

N-heterocyclic carbenes (NHC) are widely used in synthesis of various complex substances. Generated from appropriate salt NHC effect on the polarity reverse of carbonyl compound. This umpolung process effects in change of carbonyl carbon atom properties. Cocarbon atom is transformed into synthetically appropriable nucleophileNHC-catalyzed benzoin condensation between simple benzaldehyde molecules was proposed by Ronald Breslow in 1958 for thiamine well-knoin vivo conversion of pyruvic acid to acetoine which is very important step in oxidative decarboxylation of pyruvic acid. Named in his honor reaction intermediate is common acyl anion synthon which participates usually in process of condensation with other carbonyl compound molecule present in reaction mixture [2]. Moreover, it exists other way to use Breslow intermediate in organocatalysed reactions. It can be oxidized to acylesterification reactions and annulation reactions of ,

Aza-Claisen rearrangement is example of [3,3]addition of enamine to acyl-azolium generated from ,annulation6-aminouracils derivatives and cinnamyl aldehyde derivatives appears to be an attractive reagents to obtain bicyclic lactams with unprotected NHthe applicability of widely known thiazolium and triazolium salts and NHC precatalysts obtained in our team.[4-6]

The developed synthetic methodology leads to expected dihydropyridiones condensed with uracil ring for many different N,N-disubstituted 6Moreover, products were obtained with very high yields and purities. Bibliography: [1] D. M. Flanigan, F. Romanov-Michailidis, A. Nicholas. N. A. White, T. Rovis, [2] R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719-3726[3] C. Zhang, J. F. Hooper, D. W. Lupton, ACS Catal.[4] Z. Rafiski, A. Kozakiewicz, K. Rafiska, ACS Catal.[5] Z. Rafiski, A. Kozakiewicz, J. Org. Chem. 2015, [6] Z. Rafiski, ChemCatChem, 2016, 8, 2599-2604.

This work was financially supported by National Science Centre grant SONATA BIS (UMO

ORGANIC CHEMISTRY SECTIONORAL PRESENTATION

CATALYSED ANNULATION REACTION VIA AZA-CLAISEN REARRANGEMENT

Dzieszkowski, Zbigniew Rafiski

Chair of Organic Chemistry, Nicolaus Copernicus University

heterocyclic carbenes, organocatalysis, aza-Claisen rearrangement

heterocyclic carbenes (NHC) are widely used in synthesis of various complex substances. Generated from appropriate salt NHC effect on the polarity reverse of carbonyl compound. This

process effects in change of carbonyl carbon atom properties. Consequently, electrophilic ically appropriable nucleophile[1]. First mechanism of

catalyzed benzoin condensation between simple benzaldehyde molecules was proposed by known vitamin B1. This discovery gave an explanation of

conversion of pyruvic acid to acetoine which is very important step in oxidative decarboxylation of pyruvic acid. Named in his honor reaction intermediate is common acyl anion

cipates usually in process of condensation with other carbonyl compound Moreover, it exists other way to use Breslow intermediate in

organocatalysed reactions. It can be oxidized to acyl-azolium very useful interesterification reactions and annulation reactions of ,-unsaturated carbonyl compounds [3]

Claisen rearrangement is example of [3,3]-sigmatropic reaction which can occur after azolium generated from ,-unsaturated aldehyde. In that kind of

cinnamyl aldehyde derivatives appears to be an attractive reagents to obtain bicyclic lactams with unprotected NH-amide group. This reaction model broadens

nown thiazolium and triazolium salts and NHC precatalysts obtained in

The developed synthetic methodology leads to expected dihydropyridiones condensed with uracil disubstituted 6-aminouracils and cinnamyl aldehyde derivatives.

Moreover, products were obtained with very high yields and purities.

Michailidis, A. Nicholas. N. A. White, T. Rovis, J. Chem. Rev., 2015, 115, 93073726.

ACS Catal. 2017, 7, 2583-2596. ACS Catal. 2014, 4, 1404-1408.

2015, 80, 7468-7476.

This work was financially supported by National Science Centre grant SONATA BIS (UMO-2016/22/E/ST5/00469

PRESENTATION

CLAISEN

Nicolaus Copernicus University

heterocyclic carbenes (NHC) are widely used in synthesis of various complex substances. Generated from appropriate salt NHC effect on the polarity reverse of carbonyl compound. This

nsequently, electrophilic First mechanism of

catalyzed benzoin condensation between simple benzaldehyde molecules was proposed by . This discovery gave an explanation of

conversion of pyruvic acid to acetoine which is very important step in oxidative decarboxylation of pyruvic acid. Named in his honor reaction intermediate is common acyl anion

cipates usually in process of condensation with other carbonyl compound Moreover, it exists other way to use Breslow intermediate in

very useful intermediate in [3].

sigmatropic reaction which can occur after ted aldehyde. In that kind of

cinnamyl aldehyde derivatives appears to be an attractive amide group. This reaction model broadens

nown thiazolium and triazolium salts and NHC precatalysts obtained in

The developed synthetic methodology leads to expected dihydropyridiones condensed with uracil yde derivatives.

, 9307-9387.

2016/22/E/ST5/00469.)


24

BARRIER TESTS OF POLYLACTIDE FOILS

Justyna Gromowska, Ewa Olewnik-Kruszkowska, Iwona Tarach

Faculty of Chemistry, Physicochemistry of Polymers Research Group, Nicolaus Copernicus University in Toru, Poland

Keywords: polylactide, foils, polymers, barrier tests, storage tests

The current trends in food packaging involve the production of materials, which are not only suitable because of their processing parameters, but also because of their biocidal, biostatic and barrier properties.

The aim of this research was to obtain a biodegradable composite foil, which exhibits suitable structural, thermal and mechanical characteristics in combination with biodegradability and biocidal properties.

In the current work, four different foils were prepared. As a polymer matrix, a biodegradable polymer, polylactide (PLA) was used. Three different forms of PHMG (polyhexamethylene guanidine hydrochloride) were added to the polymer matrix in 1% concentrations as biocidal additives. Each foil, denoted as: L (pure PLA), LA (PLA + 1% PHMG salt of sulfanilic acid), LS (PLA + 1% PHMG stearate), LW (PLA + 1% PHMG granular polyethylene wax), had its structural and thermal properties tested.

Storage tests are obligatory in food industry. The producers need to know how long their products are fresh and safe under certain conditions. In the current research, barrier tests of prepared foils were carried out. As a tested product, unrefined hemp oil was chosen. The peroxide number was chosen as the comparison parameter of the barrier properties of tested foils. At first, the peroxide number of fresh hemp oil was determined. Subsequently, samples of oil were prepared. One sample was left open, four samples were closed with prepared foils and the last one was closed with glass cut. All samples were closed in a dark and dry place. After two and four weeks the peroxide numbers of oil samples were determined again and compared. The results showed the barrier properties of polylactide foils in comparison with the open sample and the sample closed with glass cut. Bibliography: [1] I. Cerkex, H.B. Kocer, S.D. Worley, R.M. Broughton, T.S. Huang, React Funct Polymer, 2012, 72, 673-679. [2] D. Wei, Q. Ma, Y. Guan, F. Hu, A. Zheng, X. Zhang, Z. Teng, H. Jiang, Mater Sci Eng C, 2009, 29, 1776-1780. [3] O. Kukharenko, J.F. Bardeau, I. Zaets, L. Ovcharenko, O. Tarasyuk, S. Porhyn, I. Mischenko, A. Vovk, S. Rogalsky,

N. Kozyrovska, Eur Polym J, 2014, 60, 247-254.

SEARCHING FOR COMPOUNDS EFFICIENT TO DEFEAT BACTERIAL MDR, IN THE GROUP OF ARYLIDENOIMIDAZOLONES

Aneta Kaczor, Katarzyna Kie-Kononowicz, Jadwiga Handzlik

Faculty of Pharmacy, Department of Technology and Biotechnology of Drugs,

Jagiellonian University Medical College

Keywords: arylidenoimidazolone, Dimroth rearrangement, bacterial MDR, in silico studies

The increasing bacterial multidrug resistance (MDR) to antibiotics is the significant health problem. One of the strategies to combat MDR is search for new compounds, also called adjuvants, which inhibit efflux pump, consequently increase antibiotic concentration inside the bacteria, without antibacterial activity themself. Previously, a series of active arylidenoimidazolone derivatives displayed significant efflux pump inhibitors (EPIs) action[1]. However, their usage is limited due to the toxicity.

Taking this into consideration, we extended the search for EPIs in this interesting chemical group, involving compounds with imidazolone and thiazolidinone core substituted with alkyl-amine fragments at position 2 (A) or 3 (B) and various aromatic arylidene moieties at position 5 (Fig.1).

X N

OAr

Amine

NH2

X NH

OAr

Amine

A B

Ar = 1-nafthyl, fluoreno

Amine

NH

N N

N

O

NZ

Z = O or NCH3

1-8 9-16X = N or S

Fig.1

Compounds were tested for their ADMET propertiesin silico using various bioinformatics tools, i.e. SwissADME, pkCSM, Pred Skin, Pred-hERG and Lazar toxicity predictions. The new compounds were synthesized in the 3-4 step synthesis pathways, including: (i) Knoevenagel condensation, (ii) S-methylation, (iii) condensation with proper amine, (iv) Dimroth rearrangement or N-deprotection reaction.

According to thesimulationof physicochemical properties, compounds with imidazolone core are easier soluble than thiazolidinones. In the case of ADMET properties, intestinal absorption simulated with different bioinformatics services were high for all synthesized compounds.Distribution through BBB was tested in Swiss ADME software. A few of tested compounds were able to penetrate through BBB. Theused software gave information about various toxicity aspects.

Compoundswith morpholinopiperidine moieties (5-8), were synthesized in 3-step synthesis (i-iii), while compounds with free piperazine (1-4), in 4-step synthesis with N-deprotectiongoing as deacetylation. The rest of compounds were synthesized in 4-step synthesis with Dimroth rearrangement.

In conclusion, both the study in silico and synthesis let us to obtain a series of potential EPIs with characterized druglikeness properties. The compounds will be investigated as possible antibiotics adjuvants in the microbiological studies using different bacterial strains.

Bibliography: [1] Bohnert, J., Schuster, S.; Kern, W.; Karcz T,; Olejarz, A.; Kaczor, A.; Handzlik, J.; Kie-Kononowicz, K.:

Antimicrob. Agents Chemother. 2016, 60:1974-83.

Partly supported by grant of Polish Ministry of Science no 0169/DIA/2017/46.


25

EVOLUTION OF MORPHOLOGY IN DIP-COATED PS-B-P4VP THIN FILMS

MagdalenaKonefa, AlexanderZhigunov

Department of X-ray and Neutron Structural Analysis, Institute of Macromolecular Chemistry, AS CR v.v.i., Prague, Czech Republic

Keywords: block co-polymers, self-assembly, polymer thin films, dip-coating, PS-b-P4VP

During the last decades, block copolymer (BCP) thin films have gained great interest because of their self-assembly into a nanometer-scale patterns. That ability makes them versatile substrates for applications in lithography, electronics, photonics, biomedicine, photovoltaic devices, catalysis, energy conversion or data storage [1, 2].For most applications, it is crucial to control not only the desired BCP morphology, but also the thickness and roughness of obtained thin films. These parameters depend highly on the film preparation technique as well as solvent properties. Previous investigations have shown that block copolymer thin films obtained by the dip-coating technique can exhibit different morphologies depending on dip-coating speed [2]. That leads to a powerful method for producing various nanopatterns from a single BCP solution.

In this work thin films of polystyrene-b-poly(4-vinyl piridine) (PS-b-P4VP)obtained via dip-coating methodfrom 0.5 wt%1-chloropentane solutions were investigated. PS-b-P4VP with Mn(PS) = 124 kg/mol, Mn(P4VP) = 12 kg/mol, and Mw/Mn = 1.15was used, with micellar structure and hydrodynamic radius Rh= 46.55 nm in 1-chloropentane solution (a selective solvent for PS block) , as measured by Dynamic Light Scattering and Small Angle X-Ray Scattering.

Polymer films were deposited onto silicon wafers from with withdrawal speed in the range 0.2-100 mm/min. The obtained thin films were characterized by the means of X-Ray Reflectivity, Atomic Force Microscopy and Grazing Incidence Small Angle Scattering. We report the influence of dip-coating rate on the obtained filmsmorphology, thickness and surface roughness. A V-shape dependence of film thickness vs withdrawalspeed was obtained, which indicate that the chosen dip-coating rate range allowed to cover both the capillarity and draining regimes. The data were fitted using semi-empirical model, which allows to calculate the minimum film thickness h0= 4.71nm obtained with critical dip-coating rate uC = 8.17 mm/min [3]. It was found that when one regime of film formation (capillarity or draining) is dominant, the polymer films exhibit dot morphology of P4VP blocks in a matrix of PS, with different sizes and center-to-center distances depending on the withdrawal speed. For intermediate speeds, where both mechanisms contribute in film formation, the morphology of closely packed spherical micelles with diameters about 45 nm was observed. These films also exhibited the highest RMS roughness (about 2.5 nm). Bibliography: [1] Posselt D., Zhang J., Smilgies D. M., Berezkin A. V., Potemkin I. I., Papadakis C. M., Progress in Polymer Science,

2017, 66, 80-115. [2] Roland S., Gamys C. G., Grosrenaud J., Boiss S., Pellerin C., Prudhomme R. E., Bazuin C. G., Macromolecules,

2015, 48(14), 4823-4834. [3] Faustini M., Louis B., Albouy P. A., Kuemmel M., Grosso D., The Journal of Physical Chemistry C, 2010, 114(17),

7637-7645.

This work was supported by Internal Grant no 8604 of IMC AS CR v.v.i., Prague, Czech Republic.

CATALYTIC GLYCOSYLATION: A NEW APPROACH FOR THE ACTIVATION OF TRICHLOROACETIMIDATES DONORS

Karolina Kowalska1,2,3, Christian Marcus Pedersen2

1Faculty of Chemistry, Department of Synthesis and Structure of Organic Compounds, Adam

Mickiewicz University in Pozna 2Faculty of Science, Department of Chemistry, University of Copenhagen

3Institute for Organic Chemistry, Karlsruhe Institute of Technology Keywords: carbohydrates, catalysis, stereoselectivity

Glycosylation using trichloroacetimidate donor has been one of the most commonly used methods for oligosaccharides synthesis since it was developed by Schmidt in the early eighties [1]. The reaction has been studied in detail over the years and many modifications have been made, but the classic conditions remain the most frequently used. These conditions involve catalysis by either the Lewis acid BF3OEt2 or a Brnsted acid such as a sulfonic acid most often TMSOTf, which forms TfOH in situ. Recently we have reinvestigated the activation of trichloroacetimidates.

In this communication we shall disclose the catalytic activation of trichloroacetimidate donors by TMSTNf2 or Tf2NH. Changing to Lewis or Brnsted acids with less nucleophilic counter-ions, such as TMSTNf2 or Tf2NH gave a stable intermediate bearing the activated trichloroacetimidate [2]. Preparative glycosylations [3] study revealed that this new mode of activation gave glycosides with high stereospecificity. The straightforwardly obtained -TCA donors were easily and in high yields converted to -glycosides with the inversion of anomeric stereochemistry. (Scheme 1).

Scheme 1. Stereospecific catalytic O-glycosylations of trichloroacetamidate donors

Bibliography: [1] R. R. Schmidt, J. Michel Angew. Chem. Int. Ed., 1980, 19, 731-732. [2] Y. Qiao, W. Ge, L. Jia, X. Hou, Y. Wang, C. M. Pedersen, Chem. Commun., 2016, 52, 11418-11421. [3] K. Kowalska, C.M. Pedersen, Chem. Commun., 2017, 53, 2040-2043.

O

OAc

AcOAcO

OBn O

NH

CCl3

NTfTf

TMS

O

OAc

AcOAcO

OBn O

N+

CCl3

TMSHN-

TfTf

ROHO

OPg

PgOPgO

OPg

OR

no neigbouring group participation

43 examples

easy access to - glycosides


26

THE INFLUENCE OF LASER MICRO-PATTERN ON APATITE FORMATION

Donata Kuczyska1, Marcin Pisarek2, Piotr Kwaniak1, Pawe Borowicz2, Halina Garbacz1

1 Faculty of Materials Science and Engine

XII Copernican International Young Scientists...

Documents

Transcript of XII Copernican International Young Scientists...