Synthesis and Characterization of Organotin(IV) Complexes Derived of 3-(Dimethylamino)benzoic Acid: Cytotoxic Assay on Human Liver Carcinoma Cells (HepG2)

Win Win

doi:10.3844/ajassp.2010.301.308

Abstract

Problem statement: Many studies have been carried out on organotin(IV) complexes derivative of carboxylate anions. However, the synthesis and characterization as well as the cytotoxic assay of organotin(IV) carboxylate derived of 3-(dimethylamino)benzoic acid have not been studied. Approach: Organotin(IV) carboxylate complexes derivative of 3-(dimethylamino)benzoic acid, 3-[N(CH3)2]C6H4COOH have been successfully synthesized. Two types of diorganotin(IV) complexes, [{3-[N(CH3)2]C6H4COO(R)2Sn}2O]2 dimer (R = methyl 1, butyl 3) and {3-[N(CH3)2]C6H4COO}2(C4H9)2Sn, 2 (monomer) as well as 3-[N(CH3)2]C6H4COO(C6H5)3Sn, 4 were successfully synthesized and obtained in solid state. The acid and complexes 1-4 obtained were characterized quantitatively using C, H, N and Sn elemental analysis as well as spectroscopic methods such as infrared (FTIR) and nuclear magnetic resonance (1H, 13C, 1H-13C HMQC and 119Sn NMR). In addition, complexes 1-4 obtained were screened for their cytotoxicity activity against HepG2 cells line. Results: Infrared spectroscopy showed that the coordination took place via oxygen atoms from the carboxylate anions. This indicated that the carboxylate anion acts as monodentate ligand in complexes 2 and 4. However, for distannoxane dimer (complexes 1 and 3), the carboxylate anions are found to exhibit monodentate and bidentate manner. In 119Sn NMR solution study, the tin atoms of complexes 1-3 were five-coordinated and four-coordinated in complex 4. From the 119Sn NMR, the tin atom of complex 2 was five-coordinated, this might be upon dilution, the crystal lattice were broken up resulting the carboxylate anions assembly self-arrangement. Hence, one of the carboxylate anions was located close to the tin atoms and exhibited bidentate chelation while the other carboxylate anion exhibited monodentate chelation in complex 2. Conclusion: Pure complexes 1-4 have been successfully obtained and complex 4 possessed promising biological screening activity compared to the parent acid and complexes 1-3.

Highlights

Organotin(IV) complexes are extensively studied due to the applications in industrial as well as biocidal properties (Molloy et al, 1984; Willem et al, 1997; Gielen et al, 2000)
From the 119Sn NMR, the tin atom of complex 2 was five-coordinated, this might be upon dilution, the crystal lattice were broken up resulting the carboxylate anions assembly self-arrangement
Pure complexes 1-4 have been successfully obtained and complex 4 possessed promising biological screening activity compared to the parent acid and complexes 1-3

Summary

Introduction

Organotin(IV) complexes are extensively studied due to the applications in industrial as well as biocidal properties (Molloy et al, 1984; Willem et al, 1997; Gielen et al, 2000). Numerous studies on organotin(IV) complexes have been carried out in order to study its biological properties against bacterial, fungus and cancer cells line (Teoh et al, 1997; Novelli et al, 1999; Gielen et al, 2000; Crouse et al, 2004). Applied Sci., 7 (3): 301-308, 2010 organometallic compounds as a new alternative drug bicarbonate, 100 IU mL−1 penicillin and 100 μg mL−1 in combating human cancers has been initiated due to certain side-effects of cis-platin and carboplatin as antitumour drugs (Khan et al, 2000).

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Conclusion