M. Mirisola, A. Pellerito, T. Fiore
Jun 1, 1997
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0
Influential Citations
18
Citations
Journal
Applied Organometallic Chemistry
Abstract
The synthesis, the structural features and the in vivo biological activity of diorganotin(IV) and triorganotin(IV) derivatives of [meso-tetra(4-carboxyphenyl)porphine] (H 4 TPPC) are reported. Derivatives with general formula (R 2 Sn) 2 TPPC and (R 3 Sn) 4 TPPC (R=Me, Bu, and Ph) were obtained, and the main information extracted from the infrared and Mossbauer spectral data, in the solid state, was in favor of the occurrence of five-coordinated tin(IV) atoms, in a polymeric trigonal-bipyramidal configuration, attained through two differently coordinated, estertype and chelating respectively, carboxylate anions in [R 2 Sn] 2 TPPC, while in [Alk 3 Sn] 4 TPPC five-coordination of the tin(IV) atom is reached through bridging carboxylate groups. 1 H and 13 C NMR spectra, in DMSO-d 6 or CDCl 3 suggested that the soluble derivatives, at room temperature or at 342K, were present in solution as simple monomers. The interactions of (trimethyltin) 4 [meso-tetra(4-carboxyphenyl)porphinate] (TMTPPC) and (tributyltin)4[mesa-tetra(4-carboxyphenyl)porphinate] (TBTPPC) with Bluescript KS(+) plasmid and cultured 3T3 fibroblasts were studied. Both compounds have a clear inhibitory effect on the growth of cultured mouse embryonal fibroblasts (NIH-3T3), TBTPPC being much more active. No evidence was found, however, for DNA cleavage by the compounds at molar ratios as high as 1:10 (TMTPPC, TBTPPC/DNA base pairs). According toour observations, the cytotoxicity of TBTPPC and TMTPPC does not seem to be besed on direct interation with DNA