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Organometallic Complexes with Biological Molecules: VII. Dialkyl‐ and Trialkyl‐tin (IV)[ meso ‐tetra(4‐carboxyphenyl)porphinate] Derivatives: Solid‐state, Solution‐phase Structural Aspects and In Vivo Effects
Author(s) -
Mirisola M. G.,
Pellerito A.,
Fiore T.,
Stocco G. C.,
Pellerito L.,
Cestelli A.,
Di Liegro I.
Publication year - 1997
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/(sici)1099-0739(199706)11:6<499::aid-aoc603>3.0.co;2-p
Subject(s) - chemistry , carboxylate , tetra , trigonal bipyramidal molecular geometry , tin , stereochemistry , monomer , tributyltin , molecule , chelation , in vivo , biological activity , medicinal chemistry , in vitro , organic chemistry , biochemistry , polymer , microbiology and biotechnology , biology
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 Mössbauer 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, ester‐type 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 342 K, were present in solution as simple monomers. The interactions of (trimethyltin) 4 [ meso ‐tetra(4‐carboxyphenyl)porphinate] (TMTPPC) and (tributyltin) 4 [ meso ‐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 to our observations, the cytotoxicity of TBTPPC and TMTPPC does not seem to be based on direct interaction with DNA. © 1997 John Wiley & Sons, Ltd.