Complexes in Context: Attempting to Control the Cellular Uptake … · 2011. 8. 25. · Fig. 9...

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Complexes in Context: Attempting to Control the Cellular Uptake and Localisation of Rhenium fac-Tricarbonyl Polypyridyl Complexes. Rebeca G. Balasingham, Michael P. Coogan and Flora L. Thorp-Greenwood* Electronic Supplementary Information + 2 1 Ir N N N F F N N = N N N N N N N N N N N a b c d e + Ir N N N N N = N N N 2 2 Structures of complexes 1a-e and 2. 1a b c d e 2 Confocal luminescence and bright-field images of HeLa cells: (a) cells without staining with 1a-e and 2; (b) cells incubated solely with 20 μM 1a (or 1b-e and 2) in DMSO/PBS (pH 7, 1:49, v/v) for 10 min at 25 °C; (c) DIC images of cells shown in (b); (d) overlay image of (b) and (c). The excitation wavelengths are 405 and 488 nm for complexes 1a-e and complex 2, respectively. Images and caption reproduced with permission from ref. 10. Electronic Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2011

Transcript of Complexes in Context: Attempting to Control the Cellular Uptake … · 2011. 8. 25. · Fig. 9...

Page 1: Complexes in Context: Attempting to Control the Cellular Uptake … · 2011. 8. 25. · Fig. 9 Images of cells co-stained with complex 31-33 (red) FM 4-64 (purple) and “SytoRNA

Complexes in Context: Attempting to Control the Cellular Uptake and Localisation of Rhenium fac-Tricarbonyl Polypyridyl

Complexes.

Rebeca G. Balasingham, Michael P. Coogan and Flora L. Thorp-Greenwood*

Electronic Supplementary Information

+

2

1

IrN

NN

F

F

N

N

=

N

N

N

N

N

N

N

N

N

N

N

a b c

d e+

IrN

NN N

N

=

N

N

N

2

2

Structures of complexes 1a-e and 2.

1a b c d e 2

Confocal luminescence and bright-field images of HeLa cells: (a) cells without staining with 1a-e and 2; (b) cells incubated solely with 20 μM 1a (or 1b-e and 2) in DMSO/PBS (pH 7, 1:49, v/v) for 10 min

at 25 °C; (c) DIC images of cells shown in (b); (d) overlay image of (b) and (c). The excitation wavelengths are 405 and 488 nm for complexes 1a-e and complex 2, respectively. Images and caption

reproduced with permission from ref. 10.

Electronic Supplementary Material (ESI) for Dalton TransactionsThis journal is © The Royal Society of Chemistry 2011

Page 2: Complexes in Context: Attempting to Control the Cellular Uptake … · 2011. 8. 25. · Fig. 9 Images of cells co-stained with complex 31-33 (red) FM 4-64 (purple) and “SytoRNA

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R1=R2= C6-Biotin R3=R4= H 5

R1=R2= H R3=R4= C2-Biotin 6

R1=R2= H R3=R4= C2-CONH-C6-Biotin 7

R1=R2=R3= C6-Biotin R4= Me 8

R1-R2= H R3=R4= C4 9

R1=R2= C6-Biotin R3=R4= H 5

R1=R2= H R3=R4= C2-Biotin 6

R1=R2= H R3=R4= C2-CONH-C6-Biotin 7

R1=R2=R3= C6-Biotin R4= Me 8

R1-R2= H R3=R4= C4 Structure of complexes 5-9.

2 818

2 818

Structure of complex 18

Ru

N

N

N

N

NN N

N

N

OOH

O 8

HNNH2

HN

A

2+

Structure of complexes 19 (A), 20 (B) and 21 (C).

Electronic Supplementary Material (ESI) for Dalton TransactionsThis journal is © The Royal Society of Chemistry 2011

Page 3: Complexes in Context: Attempting to Control the Cellular Uptake … · 2011. 8. 25. · Fig. 9 Images of cells co-stained with complex 31-33 (red) FM 4-64 (purple) and “SytoRNA

A B

Crystal structure of complex 58, A looking down the ‘cup’ B from outside.

1

2

3

4

R1=R2= H

R1=R2= CH3

R1= H R2= C6H5

a

b

c62

NRe

N

O

O

O

N

NH

NH

N

N

N

OH

S

R

R

R

R +1

2

3

4

R1=R2= H

R1=R2= CH3

R1= H R2= C6H5

a

b

c62

NRe

N

O

O

O

N

NH

NH

N

N

N

OH

S

R

R

R

R +

Structure of complex 62.

Electronic Supplementary Material (ESI) for Dalton TransactionsThis journal is © The Royal Society of Chemistry 2011

Page 4: Complexes in Context: Attempting to Control the Cellular Uptake … · 2011. 8. 25. · Fig. 9 Images of cells co-stained with complex 31-33 (red) FM 4-64 (purple) and “SytoRNA

Fig. 9 Images of cells co-stained with complex 31-33 (red) FM 4-64 (purple) and

“SytoRNA select” (green), with intensity profiles (same colour scheme). Reproduced with permission from ref. 36.

N

N N

N

NH2

O

OHOH

CoNN N O

NH2

NO

NH2

ONH2

ONH2

O

NH2

NH

OP O

O

OH N

N

OH

O–OOO

NH2

Structure of complex 64 reproduced with permission from ref. 68, with B12 in cartoon

form. Full molecular structure of cobalamine B12 alongside.

Electronic Supplementary Material (ESI) for Dalton TransactionsThis journal is © The Royal Society of Chemistry 2011