DOI 10.1515/mgmc-2013-0005 Main Group Met. Chem. 2013; 36(1-2): 49–55
Harminder Kaur* , Jugal Kishore Puri , Jaspreet Kaur and Kanav Dhir
Synthesis, spectroscopic and biological studies of diorganotin(IV) and triorganotin(IV) derivatives of albendazole, ofloxacin and 3-carboxypropyldisulfide Abstract: Diorganotin(IV) and triorganotin(IV) deriva-
tives of the types R 2 SnA (R = n -Bu and n -octyl) and
(R 3 Sn)
2 A (R = n -Bu), where A is the anion of albenda-
zole { methyl[(5-propylsulfanyl-3 H -benzoimidazol-2-yl)
amino]formate } , ofloxacin { ( RS )-7-fluoro-2-methyl-6-(4-
methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0 5,13 ]
trideca-5(13),6,8,11-tetraene-11-carboxylicacid } and 3-car-
boxypropyldisulfide, have been synthesized. The com-
plexes 1 – 9 obtained were characterized by elemental
analysis as well as infrared (Fourier transform infrared),
nuclear magnetic resonance ( 1 H, 13 C and 119 Sn NMR) and
ultraviolet spectroscopy. On the basis of these spectro-
scopic studies it was proposed that diorganotin complexes
of 3-carboxypropyldisulfide having 1:1 stoichiometry and
complexes of albendazole and ofloxacin having 1:2 stoi-
chiometry show tetrahedral geometry around the tin atom
with monodentate behavior of the carboxylate group in
ofloxacin and 3-carboxypropyldisulfide. Triorganotin
complexes of 3-carboxypropyldisulfide having 1:1 stoi-
chiometry and complexes of ofloxacin and albendazole
having 1:2 stoichiometry show trigonal bipyramidal geom-
etry. The ligand molecule is bound to the Sn atom through
carboxyl oxygen atoms in ofloxacin and 3-carboxypro-
pyldisulfide, and to the nitrogen atom in albendazole. The
biological activity of the synthesized complexes 4 , 5 and 6
has been screened against Candida albicans .
Keywords: albendazole; 3-carboxypropyldisulfide;
Candida albicans ; ofloxacin; organotin.
*Corresponding author: Harminder Kaur, Department of Applied Sciences, PEC University of Technology, Chandigarh 160012, India, e-mail: [email protected] Jugal Kishore Puri: Department of Chemistry, Panjab University, Chandigarh 160014, India Jaspreet Kaur: Department of Biotechnology, University Institute of Engineering and Technology, Panjab University, Chandigarh 160014, India Kanav Dhir: Department of Applied Sciences, PEC University of Technology, Chandigarh 160012, India
Introduction
Extensive use of organotin compounds in various fields
of life results in a quantum leap in organotin chemistry.
The stability and structural diversity of organotin com-
pounds make their coordination chemistry very interest-
ing (Shahzadi and Ali, 2008). One of the most rapidly
developing areas of pharmaceutical research is the dis-
covery of robust drugs for treating cancers. Cisplatin [ cis- diamminedichloroplatinum(II)] (Rosenberg et al., 1965,
1969) is an archetypical metal-based drug widely used for
treating cancer. However, it possesses serious limitations
because of inherent or acquired resistance in tumor cells
and severe side effects (Bonire and Fricker, 2001). There-
fore, there is an exigency to identify effective metal-based
therapeutics, particularly those that overcome inher-
ent and acquired resistance to drug therapy and show
improved therapeutic properties, stimulating the ongoing
investigations of alternative molecule-targeted metal-
based drugs (Storr et al., 2006). Organometallic complexes
of group 14 elements, especially tin(IV) and silicon(IV)
derivatives, have been the subject of considerable interest
(Dakternieks et al., 1997; Casas et al., 2000) owing to their
unique physical, chemical and structural properties (Jain,
1996) favorable to the environment (Ukita et al., 1999).
Recently, we have published a few papers on the chem-
istry of silicon compounds, silatranes and organolead
complexes with amino acids and dipeptides (Sandhu and
Kaur, 1990a,b; Sandhu and Hundal, 1991; Narula et al.,
2000a,b, 2002a,b, 2007; Malhotra et al., 2007; Puri et al.,
2007, 2008a,b, 2009a,b, 2011a,b; Singh et al., 2010a,b).
As all the organotin(IV) derivatives degrade by chemical
action to produce nontoxic inorganic compounds, we are
attempting to explore the chemistry of tin(IV) complexes.
Because fast and effective relief of pain and inflamma-
tion in humans with minimum side effects continues to
be a major challenge for medicinal chemistry research-
ers, many diorganotin(IV) derivatives have been found to
have the potential to be placed in the class of nonsteroidal
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50 H. Kaur et al.: Organotin derivatives of albendazole, ofloxacin and 3-carboxypropyldisulfide
anti-inflammatory drugs (Nath et al., 1999, 2003, 2004a,b,
2006; Shahzadi et al., 2005). Another important applica-
tion of organotin(IV) compounds is their use as activating
agents and templates that combine two functional groups
of the substrate (Puri and Kaur, 2005; Puri et al., 2008a,b).
Ofloxacin is a fluorinated carboxyquinolone and it is a
racemic mixture, which consists of 50% levofloxacin and
50% of its “ mirror image ” or enantiomer dextrofloxacin. It
is used as an antimicrobial agent for oral administration.
Complexes of ofloxacin have been synthesized and char-
acterized with Mg(II), Ca(II), Ba(II), Co(II), Ni(II) and Zn(II)
metal ions (Sagdinc and Bayari, 2004; Affan et al., 2009).
Albendazole is an antihelminthic drug derived from ben-
zimidazole that has a broad spectrum of activity, good tol-
erance and low cost. It has been used against human and
animal helminth parasites. The synthesis and characteriza-
tion of albendazole have been studied with Cu(II), Mn(II),
Ni(II), Co(II) and Cr(III) metal ions (El-Metwaly and Refat,
2011). In the present work, we report the synthesis, spectro-
scopic characterization and biological activities of a series
of di- and triorganotin(IV) complexes of albendazole (L 1 H),
ofloxacin (L 2 H) and 3-carboxypropyldisulfide (L 3 H).
R2SnO+2LnH R2Sn(Ln)2 +H2O
R2SnO+L3H2 R2Sn(L3)+H2O
+2LnH 2R3Sn(Ln)+H2O(R3Sn)2O
+L3H2 (n-Bu)3Sn(L3)+H2O
1; R=n-Bu, n=12; R=n-Octyl, n=14; R=n-Bu, n=2;5; R=n-Octyl, n=2
7; R=n-Bu8; R=n-Octyl
3; R=n-Bu, n=16; R=n-Bu, n=2
9[(n-Bu)3Sn]2O
A
B
C
D
Scheme 1 Azeotropic removal of water for the reaction of di/triorgano-tin oxide with albendazole, ofloxacin and 3-carboxypropyldisulfide. The abbreviation L n refers to the anion of albendazole (n = 1), ofloxacin (n = 2) and 3-carboxypropyldisulfide (n = 3), respectively. All compounds were obtained as crystalline solids. Compounds 4 , 5 and 6 are soluble in chloroform and dichloromethane, whereas compounds 1 , 2 , 3 , 7 , 8 and 9 are soluble in chloroform with one drop of dimethyl sulfoxide.
range 250 – 400 nm. Ofloxacin exhibited one main band at
299 nm, which is attributed to the carbonyl chromophore
group. The slightly longer wavelength bands in the range
NH
NH O
CH3O
SH3CN
NN
H3C
ON COOH
O
F
CH3HO
SS
O
OHO
(L1H) (L2H) (L3H2)
Results and discussion The interaction of R
2 SnO [R = n -Bu and n -octyl] and
(R 3 Sn)
2 O [R = n -Bu] with albendazole, ofloxacin and 3-car-
boxypropyldisulfide in 1:1 and 1:2 (metal/ligand) molar
ratio leads to the formation of complexes ( 1 – 9 ) with an
azeotropic removal of water (Scheme 1). All the synthe-
sized organotin(IV) complexes were obtained in good
yield (67 – 71%) and were stable toward air and moisture.
All the complexes ( 1 – 9 ) were identified by elemental anal-
ysis ( Table 1 ).
Spectroscopic data
Ultraviolet spectra
Ultraviolet (UV) spectra of organotin complexes ( 4 – 6 )
were measured at room temperature in chloroform in the
300 – 310 nm in the organotin(IV) complexes ( 4 – 6 ) are
attributed to a charge transfer transition.
Infrared spectra
Characteristic infrared (IR) frequencies (in cm -1 ) for
organotin(IV) derivatives are presented in Table 2 . The
absence of a broad band due to OH in the 2900 – 3500 cm -1
region of the carboxylic group in complexes 4 – 9 indicates
the deprotonation of this group and confirms its subse-
quent coordination through the oxygen atom and hence the
complex formation (Shahzadi et al., 2007). A strong absorp-
tion appears in the range 414 – 456 cm -1 in the spectra of com-
plexes 4 – 9 (Shahzadi et al., 2008; Shah et al., 2009) but is
absent in the spectra of the free ligand. It is assigned to the
Sn-O stretching vibration, which confirms the coordination
of carboxylate oxygen atoms to tin(IV) (Choudhary et al.,
2002). The presence of a broad band due to the imidazole
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H. Kaur et al.: Organotin derivatives of albendazole, ofloxacin and 3-carboxypropyldisulfide 51
-NH group in the spectra of complexes 1 – 3 in the range
3327 – 3337 cm -1 shows the noncoordination of the imidazole
nitrogen around the organotin moiety. The appearance of a
band in the range 423 – 456 cm -1 is assigned to ν (Sn-N) in the
spectra of complexes 1 – 3 . It shows the coordination of nitro-
gen with the organotin moiety. This band is consistent with
that detected in a number of organotin(IV)-oxygen deriva-
tives (Holmes et al., 1987; Sandhu and Hundal, 1991). In com-
plexes 4 – 9 , Δ ν between ν asy
(COO) and ν sym
(COO) is important
because these frequencies can be used to determine the type
of bonding between the metal and the carboxyl groups. The
values of Δ ѵ [ Δ ѵ = ѵ asym
(COO)-ѵ sym
(COO)] can be divided into
three groups: a) in compounds where Δ ѵ (COO) > 350; hence
the compounds contain the high probability of the presence
of monodentate carboxylate group; b) in compounds where
Δ ѵ (COO) < 200; hence the carboxylate groups of the com-
pounds can be considered as bidentate; c) in compounds
where Δ ѵ (COO) < 350 and > 200 are considered as interme-
diate between monodentate and bidentate, which is called
anisobidentate (Lebl et al., 1996). In complexes 4 – 9 , peaks
at 1708 – 1760 and 1330 – 1465 cm -1 have been assigned to the
ν asy
(COO) and ν sym
(COO) groups, respectively. In complexes
4 , 5 , 6 and 9 , the Δ ѵ value corresponds to the monodentate
Table 1 Elemental analysis and some physical properties of organotin(IV) complexes.
Sr. no.
Compound Physical state Melting point ( ° C)
Yield (%)
Molecular formula
Molecular weight
Contents (calcd/found) (%)
C H N
(1) n -Bu 2 Sn(L 1 ) 2 White solid 202 70 C 32 H 46 O 4 N 6 S 2 Sn 761.59 50.47/50.42 6.09/6.11 11.0/11.5 (2) n -Oc 2 Sn(L 1 ) 2 White solid 208 71 C 40 H 62 N 6 O 4 S 2 Sn 873.8 54.98/54.96 7.15/7.13 9.62/9.87 (3) n -Bu 3 Sn(L 1 ) 2 White solid 220 67 C 36 H 55 N 6 O 4 S 2 Sn 818.7 52.81/52.89 6.77/6.70 10.2/10.6 (4) n -Bu 2 Sn(L 2 ) 2 White solid 205 68 C 53 H 87 F 2 N 6 O 8 Sn 532.95 54.04/54.13 6.43/6.45 5.25/5.27 (5) n -Oc 2 Sn(L 2 ) 2 White solid 207 70 C 61 H 103 F 2 N 6 O 8 Sn 645.03 59.53/59.55 7.81/7.86 4.34/4.39 (6) n -Bu 3 Sn(L 2 ) 2 White solid 223 68 C 57 H 96 F 2 N 6 O 8 Sn 590.03 56.95/56.90 7.34/7.30 4.75/4.77 ( 7 ) n -Bu 2 Sn(L 3 ) White solid 210 69 C 16 H 30 O 4 S 2 Sn 469.25 40.95/41.2 6.44/6.42 13.64/13.2 (8) n -Oc 2 Sn(L 3 ) Light Yellow solid 222 70 C 24 H 46 O 4 S 2 Sn 581.46 49.57/49.50 7.97/7.95 11.01/11.14 (9) n -Bu 3 Sn(L 3 ) White solid 225 69 C 20 H 39 O 4 S 2 Sn 526.36 45.64/45.66 7.47/7.55 12.16/12.17
Table 2 Characteristic IR frequencies (in cm -1 ) of di- and triorganotin(IV) derivatives of albendazole, ofloxacin and 3-carboxypropyldisulfide.
Sr. no.
ν (C = O) ν asy (COO) ν sym (COO) ν (Sn-O) ν (Sn-C) ν (C-O)
(1) 1602 563, 596 1268 (2) 1769 562, 597 1270 (3) 1700 565 1278 (4) 1654 1714 1350 456 566, 596 1399 (5) 1657 1711 1345 414 567, 570 1375 (6) 1660 1708 1330 417 568 1370 ( 7 ) 1725 1410 418 562, 575 (8) 1760 1465 419 563, 573 (9) 1735 1380 421 558
behavior of the carboxylate group, whereas in complexes 7
and 8 , the Δ ѵ value shows the anisobidentate nature of the
carboxylic group around the organotin moiety.
Multinuclear ( 1 H and 13 C) NMR spectra
1 H NMR spectra
1 H NMR spectral data of organotin(IV) complexes are pre-
sented in Table 3 . The signal at δ 11.2 ppm due to the car-
boxylic proton in ofloxacin and 3-carboxypropyldisulfide
is absent in the spectra of complexes 4 – 9 . It indicates the
formation of the Sn-O bond and is consistent with the IR
data. The signal in the range δ 5.6 – 5.72 ppm for the imi-
dazole -NH proton in free albendazole does not undergo
any downfield shift on complex formation in 1 – 3 . It shows
the nonparticipation of imidazole nitrogen in bonding to
the central metal ion. The aromatic ring protons in the
range 7.02 – 8.9 ppm in complexes 1 – 6 suffer downfield
shift because of the deshielding of these protons due to
Table 3 1 H NMR chemical shifts ( δ , ppm) of di- and triorganotin(IV) complexes.
Sr. no.
Phenyl protons
-CH 3 -NH Sn-H- α /H- β /H- γ /H- δ up to H- ω
(1) 7.02 – 7.59 3.69 (s, 3H) 5.64 2.58 – 0.93 (2) 7.34 – 7.80 2.78 (s, 3H) 5.72 2.54 – 0.71 (3) 6.00 – 7.06 2.81 (s, 3H) 4.92 2.01 – 0.10 (4) 7.35 – 7.58 3.01 (s, 6H) 1.65 – 0.94 (5) 7.22 – 7.63 3.23 (s, 6H) 1.67 – 1.22 (6) 7.24 – 7.55 2.95 (s, 6H) 1.54 – 0.69 ( 7 ) 2.43 (s, 6H) 2.39 – 0.85 (8) 2.66 (s, 6H) 2.62 – 0.79 (9) 2.41 (s, 6H) 2.81 – 0.94
Sn-CH 2 -CH 2 -CH 2 -CH 3 ; Sn-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 3 .
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52 H. Kaur et al.: Organotin derivatives of albendazole, ofloxacin and 3-carboxypropyldisulfide
the drainage of electron density from ring to metal atom
(Sagdinc and Bayari, 2004; Affan et al., 2009). All the
protons in the complexes 1 – 9 have been identified, and
the total numbers of protons calculated from the integra-
tion curves are in agreement with those calculated by
incremental method (Danish et al., 1995).
13 C NMR spectra
13 C NMR spectral data along with the assignment of
characteristic peaks of all the synthesized organotin(IV)
complexes are presented in Table 4 . The peak at 161.6 –
171.2 ppm has been assigned to the -C = O, which does not
undergo any shift on complexation. It illustrates the non-
participation of this group in complexes 1 – 6 . The signals
in the range 115 – 134 ppm, which have been assigned to
the aromatic carbons of free albendazole and ofloxacin,
suffer significant downfield shift on complexation in
1 – 6 . The appearance of peaks in the range 23.7 – 41.5 ppm,
which has been assigned to the Sn-C peaks of the butyl
and octyl groups, confirms the complex formation in the
complexes 1 – 9 (Sandhu and Kaur, 1990a,b, 1991). All
magnetically nonequivalent carbons of alkyl or phenyl
groups attached to the tin have been identified, and their
chemical shifts are in close agreement with the reported
values.
119 Sn NMR
The possibility of detecting the presence of coordinative
different organotin(IV) moieties was explored by acqui-
sition of 119 Sn NMR spectra. The 119 Sn chemical shifts
usually cover a range, quoted relative to tetramethyltin,
with increasing coordination number of tin producing a
Table 4 13 C NMR spectral data of di- and triorganotin(IV) complexes.
Sr. no.
C == O -COO Ph-C Sn-(C- α to C- ω )
(1) 168.8 121.7 – 109.9 40.1 – 37.3 (2) 171.2 124.9 – 111.0 40.2 – 39.1 (3) 169.7 120.9 – 112.8 40.5 – 38.3 (4) 160.5 172.1 115.7 – 131.0 40.1 – 38.8 (5) 161.6 173.4 117.9 – 132.8 40.3 – 38.6 (6) 165.8 171.7 117.2 – 134.8 40.0 – 38.4 ( 7 ) 172.3, 182.7 – 27.2 – 24.0 (8) – 171.6, 183.8 – 28.4 – 25.6 (9) – 176.6, 185.5 – 29.7 – 23.7
Sn-CH 2 -CH 2 -CH 2 -CH 3 ; Sn-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 3 .
large upfield shift for δ ( 119 Sn). 119 Sn NMR spectral data of
complex 7 depicted a single resonance signal at δ value
-143. As indicated by the single value, trigonal bipyrami-
dal geometry around the tin atom is proposed in this poly-
meric structure (Holecek et al., 1986).
Antifungal activity
The synthesized complexes ( 1 – 9 ) are checked in dimethyl
sulfoxide, chloroform, methanol, ethanol and dichlo-
romethane for their solubility, but the complexes ( 4 – 6 )
are soluble in CHCl 3 . The complexes ( 4 – 6 ) are screened
against Candida albicans for their antifungal activity.
Percentage inhibition of complexes ( 4 – 6 ) is presented in
Table 5 . Triorganotin(IV) complex ( 6 ) is found to be more
active than diorganotin(IV) derivatives ( 4 – 5 ).
Conclusion Organotin(IV) complexes of albendazole, ofloxacin and
3-carboxypropyldisulfide have been synthesized in 1:1
and 1:2 (metal: ligand) molar ratio through azeotropic
removal of water. The spectroscopic studies of all the
synthesized complexes suggest a tetrahedral geometry
in diorganotin complexes of albendazole and ofloxacin,
whereas trigonal bipyramidal in 3-carboxypropyldi-
sulfide (Holecek et al., 1986; Lebl et al., 1996). In trior-
ganotin complexes of albendazole, ofloxacin and 3-car-
boxypropyldisulfide, trigonal bipyramidal geometry is
observed (Lebl et al., 1996). The antifungal activity of all
the studied complexes revealed that the activity increases
on complexation, and the triorganotin complexes are
found to be more active than diorganotin complexes. UV
spectroscopic studies for the complexes 4 – 6 further show
the nonparticipation of the hetero atoms (other than the
coordinating atoms) present in the ligands in bonding to
the central tin metal ion.
Table 5 Antifungal activity for organotin(IV) complexes of ofloxacin.
Sr. no.
Solvent/complex
Average % inhibition after 24 h
C. albicans
Conc. (0.80 mg/ml)
Conc. (0.40 mg/ml)
I CHCl 3 / n -Bu 2 Sn(L 2 ) 2 7.5 43.9 II CHCl 3 / n -octyl 2 Sn(L 2 ) 2 7.4 41.2 III CHCl 3 / n -Bu 3 Sn(L 2 ) 2 12.5 62.4
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H. Kaur et al.: Organotin derivatives of albendazole, ofloxacin and 3-carboxypropyldisulfide 53
Experimental
Materials All the di- and triorganotin(IV) compounds were purchased from
Alpha products (Sigma-Aldrich, New Delhi, India) and were used as
such. All the reactions were carried out under anhydrous conditions.
The solvents used were dried before use according to the literature
method (Armarego and Chai, 2003).
Instruments and measurements Melting points were determined in a capillary tube on an electro-
thermal melting point apparatus. UV spectra for the complexes were
recorded at 250 – 500 nm with a Systronics Double beam spectropho-
tometer 2203. IR spectra for the complexes ( 1 – 9 ) were recorded on a
PerkinElmer FTIR spectrophotometer at 4000 – 200 cm -1 . The 1 H NMR,
13 C and 119 Sn NMR were recorded on a Bruker Avance II 400 NMR
spectrometer. All chemical shift values were reported with respect to
tetramethylsilane as internal solvent. Carbon, hydrogen and nitrogen
(CHN) analysis of the samples was performed on the PerkinElmer
model 2400 CHN Analyzer.
Synthesis of dibutyltin, dioctyltin and bis(tributyltinoxide) complexes of albendazole, ofloxacin and 3-carboxypropyldisulfide Dialkyl/trialkyltin(IV) oxide (1 mmol) and the ligands (L 1 H, L 2 H) (2
mmol) and (L 3 H 2 ) (1 mmol) were dissolved in a mixture of dry ben-
zene (30 ml) and methanol (L 1 H, L 2 H, L 3 H 2 ) (10 ml). The reaction mix-
ture was then heated at refl ux and the water was removed by azeo-
tropic distillation. The dialkyl/trialkyltin(IV) oxide dissolved within
10 – 15 min to give a clear solution. Refl uxing was further continued
for 3 – 4 h and the contents were fi ltered and then cooled. Excess sol-
vent was removed by distillation, leaving behind a solid complex.
All the solids were recrystallized from the mixture of methanol and
hexane (5:1) and dried in vacuo at 40 – 50 ° C for 2 – 3 h. Purity of the
complexes was checked by thin-layer chromatography using silica
gel-G as adsorbent.
Antifungal activity The biological activity for the synthesized complexes was studied on
C. albicans , a representative model organism used to screen the anti-
fungal activity. The organism was procured from the Microbial Type
Culture Collection Centre, Institute of Microbial Technology, Chan-
digarh, India. To study the eff ects of newly synthesized complexes,
these were dissolved in dimethyl sulfoxide/chloroform/methanol/
ethanol and dichloromethane and kept at 4 ° C until further use.
The organism was cultured in Sabouraud dextrose broth medium at
30 ° C and then subcultured aft er every 36 h so as to maintain it in log
phase. For all the experiments, actively proliferating log phase cells
were taken, and the antifungal activities of various complexes were
studied by growing the cells at the fi nal concentrations of 0.80 and
0.40 mg/ml in a total of 2 ml of culture medium. Cells of C. albicans
were counted with a hemocytometer, and 1 × 10 5 cells per milliliter of
the medium were used as inoculum. Growth of cells was measured by
optical density measurement at 600 nm. Experiments were conducted
with the yeast form of C. albicans grown at 30 ° C in the presence of the
above complexes at the fi nal concentrations of 0.80 and 0.40 mg/ml.
Cell turbidity was measured aft er 24 h at 600 nm.
Acknowledgments: We are thankful to the Department of
Applied Sciences, PEC University of Technology, Chandi-
garh, India, for financial support. We are also grateful to
the head of the chemistry department, Panjab University,
and the University Institute of Engineering and Technol-
ogy, Chandigarh, for providing instrumental facilities for
product analysis. Dr. J. K. Puri, former professor and head
of inorganic chemistry, Punjab University, is thankful to
the University Grant Commission for the award of Emeritus
Professor Fellow 2010 in order to continue his research.
Received November 15, 2011; accepted January 22, 2013
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