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Organometallic complexes with biological molecules II. Synthesis, solid‐state characterization and in vivo Cytotoxicity of Diorganotin(IV)chloro and Triorganotin(IV)chloro derivatives of Penicillin G
Author(s) -
Maggio F.,
Pellerito A.,
Pellerito L.,
Grimaudo S.,
Mansueto C.,
Vitturi R.
Publication year - 1994
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/aoc.590080112
Subject(s) - chemistry , trigonal bipyramidal molecular geometry , denticity , carboxylate , medicinal chemistry , stereochemistry , tin , quadrupole splitting , molecule , crystallography , mössbauer spectroscopy , organic chemistry , crystal structure
Abstract Several new diorganotin(IV)chloro and triorganotin(IV)chloro penicillin G derivatives have been prepared. The isolated compounds showed 1:1 stoichiometry, with formulae R 2 SnClpenG and R 3 SnClpenGNa, respectively (penG − = penicillin G − = 4‐ thia ‐ 1 ‐ azabicyclo[3.2.0]heptane‐2‐carboxylate, 3,3‐dimethyl‐7‐oxo‐6‐(2‐phenylacet‐amido) anion; R = Me, Bu, Ph). The coordination environment around the the tin(IV) atom, in all of the complexes, was trigonal bipyramidal. Penicillin G behaved as a monoanionic, bismonodentate ligand in R 2 SnClpenG through the β‐lactamic carbonyl and unidentate ester‐type carboxylate anion, and as unidentate through the β‐lactamic carbonyl in R 3 SnClpenGNa, as inferred on the basis of IR spectra. The rationalization of the Mössbauer parameter nuclear quadrupole splitting, Δ E (mm s −1 ), according to the point‐charge model formalism, supported such an hypothesis. The partial atomic charges on tin atoms, Q Sn , calculated for all the diorganotin(IV)chloropenG and triorganotin(IV)chloropenGNa compounds by the CHELEQ program, correlated well with the experimental 119 Sn Mössbauer parameter isomer shift, δ (mm s −1 ). The δ/Q Sn data for diorganotin(IV)chloropenG and for triorganotin(IV)‐chloropenGNa dervatives have been correlated with the δ/Q Sn values of triorganotin(IV) halide, cyanide, thiocyanate and cyanate compounds, whose trigonal bipyramidal polymeric structure has been well established. Finally, the biological activity of diorganotin(IV)chloropenG and triorganotin(IV)chloropenGNa derivatives has been tested using Ciona intestinalis fertilized eggs at different stages of development.