Search

New organotin(IV) derivatives with general formulae R2SnL, where R = n−Bu and L is the dianion of glycyltyrosine (H2L‐1), glycyltryptophane (H2L‐2), leucyltyrosine (H2L‐3), leucylleucine (H2L‐4), valylvaline (H2L‐5) and alanylvaline (H2L‐6) have been synthesized in 1 : 1 molar ratio by the reaction of Bu2SnO with the respective dipeptide under azeotropic removal of water. Triphenyltin glycylleucinate was obtained by reacting Ph3SnCl and sodium glycylleucinate with filtration of NaCl formed. The bonding and coordination behaviour in these derivatives are discussed on the basis of IR, multinuclear 1H, 13C and 117Sn magnetic resonance and 119Sn Mössbauer spectroscopic studies. These investigations suggest that all the ligands in R2SnL act as dianionic tridentates coordinating through the COO−, NH2and Npeptidegroups, whereas in Ph3Sn(HL) the ligand acts as a bidentate coordinating through the COO−and NH2groups. The 119Sn Mössbauer studies, together with the NMR data, indicate that, for the 1 : 1 monomeric derivatives, the polyhedron around tin in R2SnL is a trigonal bipyramid with the butyl groups and Npeptidein the equatorial positions, while the axial positions are occupied by a carboxylic oxygen and the amino nitrogen atom. In Ph3Sn(HL) the structure is intermediate between pseudotetrahedral and cis‐trigonal bipyramidal, with the Naminoand two phenyl groups in the equatorial plane and the carboxylate oxygen and the third phenyl group in axial positions. All the complexes have been screened against seven cancer cell lines of human origin, viz. MCF‐7, EVSA‐T, WiDr, IGROV, M19, MEL A498 and H226. Ph3Sn(HL) displays the lowest ID50values of the tin compounds tested and reported in this paper. Its activity is comparable to those of methotrexate and 5‐fluorouracil. All the di‐n‐butyltin compounds exhibit lower in vitroanti‐tumour activities than Ph3Sn(HL); however, they do provide significantly better activities than etoposide and cis‐platin. Copyright © 2003 John Wiley & Sons, Ltd.

New organotin(IV) derivatives with general formulae R2SnL, where R = n−Bu and L is the dianion of glycyltyrosine (H2L-1), glycyltryptophane (H2L-2), leucyltyrosine (H2L-3), leucylleucine (H2L-4), valylvaline (H2L-5) and alanylvaline (H2L-6) have been synthesized in 1 : 1 molar ratio by the reaction of Bu2SnO with the respective dipeptide under azeotropic removal of water. Triphenyltin glycylleucinate was obtained by reacting Ph3SnCl and sodium glycylleucinate with filtration of NaCl formed. The bonding and coordination behaviour in these derivatives are discussed on the basis of IR, multinuclear ¹H, ¹³C and ¹¹⁷Sn magnetic resonance and ¹¹⁹Sn Mössbauer spectroscopic studies. These investigations suggest that all the ligands in R2SnL act as dianionic tridentates coordinating through the COO⁻, NH2 and Npeptide groups, whereas in Ph3Sn(HL) the ligand acts as a bidentate coordinating through the COO⁻ and NH2 groups. The ¹¹⁹Sn Mössbauer studies, together with the NMR data, indicate that, for the 1 : 1 monomeric derivatives, the polyhedron around tin in R2SnL is a trigonal bipyramid with the butyl groups and Npeptide in the equatorial positions, while the axial positions are occupied by a carboxylic oxygen and the amino nitrogen atom. In Ph3Sn(HL) the structure is intermediate between pseudotetrahedral and cis-trigonal bipyramidal, with the Namino and two phenyl groups in the equatorial plane and the carboxylate oxygen and the third phenyl group in axial positions. All the complexes have been screened against seven cancer cell lines of human origin, viz. MCF-7, EVSA-T, WiDr, IGROV, M19, MEL A498 and H226. Ph3Sn(HL) displays the lowest ID50 values of the tin compounds tested and reported in this paper. Its activity is comparable to those of methotrexate and 5-fluorouracil. All the di-n-butyltin compounds exhibit lower in vitro anti-tumour activities than Ph3Sn(HL); however, they do provide significantly better activities than etoposide and cis-platin. Copyright © 2003 John Wiley & Sons, Ltd.

Four di‐n‐butyltin(IV) derivatives of bis(carboxymethyl)benzylamines were synthesized and their structure characterized by 1H,13C and ­117/119Sn NMR, Mössbauer spectroscopy and mass spectrometry. The derivative substituted in the meta position by a methyl group has been further characterized by X‐ray crystallography. This compound exhibits a distorted trigonal bipyramidal geometry at tin. The NMR data in solution, as well as other spectroscopic results in the solid state, confirm this structure for all the compounds. Evidence is provided to show that the compounds are more highly associated in concentrated solution than in the solid state. Their in vitroantitumour activity is reported. Copyright © 2001 John Wiley & Sons, Ltd.

Four di-n-butyltin(IV) derivatives of bis(carboxymethyl)benzylamines were synthesized and their structure characterized by ¹H,¹³C and ­^117/119Sn NMR, Mössbauer spectroscopy and mass spectrometry. The derivative substituted in the meta position by a methyl group has been further characterized by X-ray crystallography. This compound exhibits a distorted trigonal bipyramidal geometry at tin. The NMR data in solution, as well as other spectroscopic results in the solid state, confirm this structure for all the compounds. Evidence is provided to show that the compounds are more highly associated in concentrated solution than in the solid state. Their in vitro antitumour activity is reported. Copyright © 2001 John Wiley & Sons, Ltd.