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Preliminary in vitro Cytotoxic Assay on HepG2 and Antibacterial Screening Activity: Synthesis and Characterization of Organotin(IV) Complexes Derivatives of 2-Methyl-3-nitrobenzoic Acid
Corresponding Author(s) : Yip-Foo Win
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
Three organotin(IV) carboxylate complexes derivatives of 2-methyl-3-nitrobenzoic acid (HL) have been successfully synthesized and characterized quantitatively and qualitatively. The complexes obtained are screened for their preliminary in vitro cytotoxic assay on human liver hepatocellular carcinoma cells (HepG2) and antibacterial screening activity. Results of the infrared and NMR spectroscopy on the acid and complexes showed that the coordination took place via oxygen atoms from the carboxylate anions. With the exceptional case, based on the spectroscopy studies indicated that one methanol molecule also take part in the coordination to tin(IV) atom moiety in complex 3 resulting the tin(IV) atom exhibited five coordination in solid state. From the preliminary in vitro cytotoxic assay on HepG2 and antibacterial screening activity, triphenyltin(IV) (complex 3) showed slightly better activity compared to diorganotin(IV) complexes (1 and 2).
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- R. Zhang, J. Sun and C. Ma, J. Organomet. Chem., 690, 4366 (2005).
- Y.F. Win, S.G. Teoh, J.B.-J. Teh, H.K. Fun and L. Zakaria, Acta Cryst., E63, m323 (2007).
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- Y.-F. Win, C.-S. Choong, S.-T. Ha, S.-G. Teoh and N.E. Eltayeb, Asian J. Chem., 25, 972 (2013).
- Y.-F. Win, S.G. Teoh, B.M. Yamin and S.W. Ng, Acta Cryst., E66, m1164 (2010).
- K.C. Molloy, T.G. Purcell, K. Quill and I.W. Nowell, J. Organomet. Chem., 267, 237 (1984).
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- S.G. Teoh, S.H. Ang, S.B. Teo, H.K. Fun, K.L. Khew and C.W. Ong, J. Chem. Soc., Dalton Trans., 4, 465 (1997).
- F. Novelli, M. Recine, F. Sparatore and C. Juliano, IL Farmaco, 54, 237 (1999).
- M. Gielen, M. Biesemans, D.D. Vos and R. Willem, J. Inorg. Biochem., 79, 139 (2000).
- K.A. Crouse, K.-B. Chew, M.T.H. Tarafder, A. Kasbollah, A.M. Ali, B.M. Yamin and H.K. Fun, Polyhedron, 23, 161 (2004).
- Y.-F. Win, S.-G. Teoh, M.R. Vikneswaran, S.-T. Ha and I. Pazilah, Int. J. Phys. Sci., 5, 1263 (2010).
- Y.-F. Win, S.-G. Teoh, S.-T. Ha, L.G.-A. Ong and T.-S. TengkuMuhammad, Int. J. Phys. Sci., 6, 1463 (2011).
- T. Mosmann, J. Immunol. Methods., 65, 55 (1983).
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- G.K. Sandhu and S.P. Verma, Polyhedron, 6, 587 (1987).
- L.L. Yeap and S.G. Teoh, J. Coord. Chem., 56, 701 (2003).
- A. Sau and R.R. Holmes, J. Organomet. Chem., 217, 157 (1981).
- M. Danish, H.G. Alt, A. Badshah, S. Ali, M. Mazhar and N. Islam, J. Organomet. Chem., 486, 51 (1995).
- J. Holecek, K. Handlír, M. Nádvornik and A. Lycka, J. Organomet. Chem., 258, 147 (1983).
- J. Holecek, M. Nadvorník, K. Handlír and A. Lycka, J. Organomet. Chem., 241, 177 (1983).
- T.S.B. Baul, S. Dhar, S.M. Pyke, E.R.T. Tiekink, E. Rivarola, R. Butcher and F.E. Smith, J. Organomet. Chem., 633, 7 (2001).
- J. Holecek, M. Nádvornik, K. Handlír and A. Lycka, J. Organomet. Chem., 315, 299 (1986).
- W. Rehman, M.K. Baloch and A. Badshah, J. Braz. Chem, Soc., 4, 827 (2005).
- K. Shahid, S. Shahzadi, S. Ali and M. Mazhar, Bull. Korean Chem. Soc., 27, 44 (2006).
- M.S. Ahmad, M. Hussain, M. Hanif, S. Ali and B. Mirza, Molecules, 12, 2348 (2007).
- Z.H. Chohan, M. Arif, M.M. Akhtar and C.T. Supuran, Bioinorg. Chem. Appl., 2006, 83131 (2006)
References
R. Zhang, J. Sun and C. Ma, J. Organomet. Chem., 690, 4366 (2005).
Y.F. Win, S.G. Teoh, J.B.-J. Teh, H.K. Fun and L. Zakaria, Acta Cryst., E63, m323 (2007).
Y.-F. Win, S.G. Teoh, M.R. Vikneswaran, J.H. Goh and H.K. Fun, Acta Cryst., E66, m695 (2010).
Y.-F. Win, C.-S. Choong, S.-T. Ha, C.K. Quah and H.K. Fun, Acta Cryst., E67, m535 (2011).
Y.-F. Win, C.-S. Choong, S.-T. Ha, S.-G. Teoh and N.E. Eltayeb, Asian J. Chem., 25, 972 (2013).
Y.-F. Win, S.G. Teoh, B.M. Yamin and S.W. Ng, Acta Cryst., E66, m1164 (2010).
K.C. Molloy, T.G. Purcell, K. Quill and I.W. Nowell, J. Organomet. Chem., 267, 237 (1984).
R. Willem, A. Bouhdid, B. Mahieu, L. Ghys, M. Biesmans, E.R.T. Tiekink, D. de Vos and M. Gielen, J. Organomet. Chem., 531, 151 (1997).
S.G. Teoh, S.H. Ang, S.B. Teo, H.K. Fun, K.L. Khew and C.W. Ong, J. Chem. Soc., Dalton Trans., 4, 465 (1997).
F. Novelli, M. Recine, F. Sparatore and C. Juliano, IL Farmaco, 54, 237 (1999).
M. Gielen, M. Biesemans, D.D. Vos and R. Willem, J. Inorg. Biochem., 79, 139 (2000).
K.A. Crouse, K.-B. Chew, M.T.H. Tarafder, A. Kasbollah, A.M. Ali, B.M. Yamin and H.K. Fun, Polyhedron, 23, 161 (2004).
Y.-F. Win, S.-G. Teoh, M.R. Vikneswaran, S.-T. Ha and I. Pazilah, Int. J. Phys. Sci., 5, 1263 (2010).
Y.-F. Win, S.-G. Teoh, S.-T. Ha, L.G.-A. Ong and T.-S. TengkuMuhammad, Int. J. Phys. Sci., 6, 1463 (2011).
T. Mosmann, J. Immunol. Methods., 65, 55 (1983).
A.M. Ali, N.H. Ismail, M.M. Mackeen, L.S. Yazan, S.M. Mohamed, A.S.H. Ho and N.H. Lajis, Pharmaceut. Biol., 38, 298 (2000).
G.K. Sandhu and S.P. Verma, Polyhedron, 6, 587 (1987).
L.L. Yeap and S.G. Teoh, J. Coord. Chem., 56, 701 (2003).
A. Sau and R.R. Holmes, J. Organomet. Chem., 217, 157 (1981).
M. Danish, H.G. Alt, A. Badshah, S. Ali, M. Mazhar and N. Islam, J. Organomet. Chem., 486, 51 (1995).
J. Holecek, K. Handlír, M. Nádvornik and A. Lycka, J. Organomet. Chem., 258, 147 (1983).
J. Holecek, M. Nadvorník, K. Handlír and A. Lycka, J. Organomet. Chem., 241, 177 (1983).
T.S.B. Baul, S. Dhar, S.M. Pyke, E.R.T. Tiekink, E. Rivarola, R. Butcher and F.E. Smith, J. Organomet. Chem., 633, 7 (2001).
J. Holecek, M. Nádvornik, K. Handlír and A. Lycka, J. Organomet. Chem., 315, 299 (1986).
W. Rehman, M.K. Baloch and A. Badshah, J. Braz. Chem, Soc., 4, 827 (2005).
K. Shahid, S. Shahzadi, S. Ali and M. Mazhar, Bull. Korean Chem. Soc., 27, 44 (2006).
M.S. Ahmad, M. Hussain, M. Hanif, S. Ali and B. Mirza, Molecules, 12, 2348 (2007).
Z.H. Chohan, M. Arif, M.M. Akhtar and C.T. Supuran, Bioinorg. Chem. Appl., 2006, 83131 (2006)