A New Platinum Complex With Tryptophan: Synthesis, Structural Characterization, Dft Studies And Biological Assays In Vitro Over Human Tumorigenic Cells

A new platinum(II) complex with the amino acid L-tryptophan (trp), named Pt-trp, was synthesized and characterized. Elemental, thermogravimetric and ESI-QTOF mass spectrometric analyses led to the composition [Pt(C 11H11N2O2)2] ×6H2O. Infrared spectroscopic data indicate the coordination of trp to Pt(II) through the oxygen of the carboxylate group and also through the nitrogen atom of the amino group. The 13C CP/MAS NMR spectroscopic data confirm coordination through the oxygen atom of the carboxylate group, while the 15N CP/MAS NMR data confirm coordination of the nitrogen of the NH2 group to the metal. Density functional theory (DFT) studies were applied to evaluate the cis and trans coordination modes of trp to platinum(II). The trans isomer was shown to be energetically more stable than the cis one. The Pt-trp complex was evaluated as a cytotoxic agent against SK-Mel 103 (human melanoma) and Panc-1 (human pancreatic carcinoma) cell lines. The complex was shown to be cytotoxic over the considered cells. © 2013 Elsevier B.V. All rights reserved.122209215Barefoot, R.R., (2001) J. Chromatogr. B, 751, pp. 205-211Lebwohl, D., Canetta, R., (1998) Eur. J. Cancer, 34, pp. 1522-1534Rafique, S., Idrees, M., Nasim, A., Akbar, H., Athar, A., (2010) Biotechnol. Mol. Biol. Rev., 5, pp. 38-45Kelland, L., (2007) Nat. Rev. Cancer, 7, pp. 573-584Ivanov, A.I., Christodoulou, J., Parkinson, J.A., Barnham, K.J., Tucker, A., Woodrow, J., Sadler, P.J., (1998) J. Biol. Chem., 273, pp. 14721-14730Khalailar, I., Allardyce, C.S., Verna, C.S., Dyson, P.J., (2005) ChemBioChem, 6, pp. 1788-1795Cutillas, N., Yellol, G.S., Haro, C., Vicente, C., Rodriguez, V., Ruiz, J., (2013) Coord. Chem. Rev., 257, pp. 2784-2797Chiririwa, H., Moss, J.R., Hendricks, D., Smith, G.S., Meijboom, R., (2013) Polyhedron, 49, pp. 29-35Castello, W.S., Spera M B, M., Gomes, A.F., Gozzo, F.C., Lustri, W.R., Formiga, A.L.B., Corbi, P.P., (2011) J. Coord. Chem., 64, pp. 272-280Spera, M.B.M., Quintão, F.A., Ferraresi, D.K.D., Lustri, W.R., Magalhães, A., Formiga, A.L.B., Corbi, P.P., (2011) Spectrochim. Acta A, 78, pp. 313-318Corbi, P.P., Massabni, A.C., Moreira, A.G., Medrano, F.J., Jasiulionis, M.G., Costa-Neto, C.M., (2005) Can. J. Chem.-Revue Canadienne de Chimie, 83, pp. 104-109Corbi, P.P., Massabni, A.C., (2006) Spectrochim. Acta A, 64, pp. 418-419Cavicchioli, M., Massabni, A.C., Heinrich, T.A., Costa-Neto, C.M., Abrão, E.P., Fonseca, B.A.L., Castellano, E.E., Leite, C.Q.F., (2010) J. Inorg. Biochem., 104, pp. 533-540Dunbar, R.C., Steill, J.D., Polfer, N.C., Oomens, J., (2008) J. Phys. Chem. A, 112, pp. 10823-10830Wagner, C.C., Baran, E.J., (2004) Acta Farm. Bonaerense, 23, pp. 339-342Kazachenko, A.S., Legler, A.V., Peryanova, O.V., Vstavskaya, Y.A., (2000) Pharm. Chem. J., 34, pp. 257-258Carvalho, M.A., Souza, B.C., Paiva, R.E.F., Bergamini, F.R.G., Gomes, A.F., Gozzo, F.C., Lustri, W.R., Corbi, P.P., (2012) J. Coord. Chem., 65, pp. 1700-1711Carvalho, M.A., De Paiva, R.E.F., Bergamini, F.R.G., Gomes, A.F., Gozzo, F.C., Lustri, W.R., Formiga, A.L.B., Corbi, P.P., (2013) J. Mol. Struct., 1031, pp. 125-131Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Matsunaga, S.K.N., Montgomery, Jr.J.A., (1993) J. Comput. Chem., 14, pp. 1347-1363Hay, P.J., Wadt, W.R., (1985) J. Chem. Phys., 82, pp. 299-310Ditchfie, R., Hehre, W.J., Pople, J.A., (1971) J. Chem. Phys., 54, pp. 724-728Hehre, W.J., Ditchfie, R., Pople, J.A., (1972) J. Chem. Phys., 56, pp. 2257-2261Francl, M.M., Pietro, W.J., Hehre, W.J., Binkley, J.S., Gordon, M.S., Defrees, D.J., Pople, J.A., (1982) J. Chem. Phys., 77, pp. 3654-3665Harihara, P.C., Pople, J.A., (1973) Theor. Chim. Acta, 28, pp. 213-222Becke, A.D., (1993) J. Chem. Phys., 98, pp. 5648-5652Lee, C.T., Yang, W.T., Parr, R.G., (1988) Phys. Rev. B, 37, pp. 785-789Miertus, S., Scrocco, E., Tomasi, J., (1981) Chem. Phys., 55, pp. 117-129Bonacin, J.A., Formiga, A.L.B., Melo, V.H.S., Toma, H.E., (2007) Vib. Spectrosc., 44, pp. 133-141Scott, A.P., Radom, L., (1996) J. Phys. Chem., 100, pp. 16502-16513Mosmann, T., (1983) J. Immunol. Methods, 65, pp. 55-63(1994) Powder Diffraction Database - CD ROM, , File 46-1043 (JCPDS-ICDD)Hu, J., Fu, R., Ye, C., (1992) Chem. Phys. Lett., 195, pp. 159-162Çakir, S., Biçer, E., (2010) J. Chil. Chem. Soc., 55, pp. 236-239Gao, H., (2011) Spectrochim. Acta A, 79, pp. 687-69