Antiproliferative and anti-tumor activity of organotin compounds

Recent developments in penta-, hexa- and heptadentate Schiff base ligands and their metal complexes

Schiff bases are the most widely used versatile ligands, able to coordinate many elements and to stabilize them in various oxidation states. Recently, this class of compounds has been employed as models for biological systems, and in control of stereochemistry in six-coordinate transition metal complexes. Recently, the chemistry of organotin(IV) complexes of Schiff bases has also stemmed from their antitumour, antimicrobial, antinematicidal, anti-insecticidal and anti-inflammatory activities. Furthermore, organotin(IV) complexes of Schiff bases present a wide variety of interesting structural possibilities. Both aliphatic and aromatic Schiff bases in their neutral and deprotonated forms have been used to yield adducts and chelates with variable stoichiometry and different modes of coordination. This critical review (>155 references) focuses upon the chemistry and biological applications of organotin(IV) complexes of Schiff bases reported in the past 15 years. Thermal behavior of these complexes is also discussed.

Chemistry and applications of organotin(IV) complexes of Schiff bases

Biological activity studies on organotin(IV)n+ complexes and parent compounds

https://holcapek.upce.cz/reprints/RE_JCA_1217_2010_3908_Spectra_interpretation_review.pdf

Basic rules for the interpretation of atmospheric pressure ionization mass spectra of small molecules.

New organotin(IV) derivatives with general formulae R 2 SnL, where R = n-Bu and L is the dianion of glycyltyrosine (H 2 L-1), glycyltryptophane (H 2 L-2), leucyltyrosine (H 2 L-3), leucylleucine (H 2 L-4), valylvaline (H 2 L-5) and alanylvaline (H 2 L-6) have been synthesized in 1:1 molar ratio by the reaction of Bu 2 SnO with the respective dipeptide under azeotropic removal of water. Triphenyltin glycylleucinate was obtained by reacting Ph 3 SnCl and sodium glycylleucinate with filtration of NaCl formed. The bonding and coordination behaviour in these derivatives are discussed on the basis of IR, multinuclear 1 H, 13 C and 117 Sn magnetic resonance and 119 Sn Mossbauer spectroscopic studies. These investigations suggest that all the ligands in R 2 SnL act as dianionic tridentates coordinating through the COO-, NH 2 and N peptide groups, whereas in Ph 3 Sn(HL) the ligand acts as a bidentate coordinating through the COO- and NH 2 groups. The 119 Sn Mossbauer studies, together with the NMR data, indicate that, for the 1:1 monomeric derivatives, the polyhedron around tin in R 2 SnL is a trigonal bipyramid with the butyl groups and N peptide in the equatorial positions, while the axial positions are occupied by a carboxylic oxygen and the amino nitrogen atom. In Ph 3 Sn(HL) the structure is intermediate between pseudotetrahedral and cis-trigonal bipyramidal, with the N amino 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. Ph 3 Sn(HL) displays the lowest ID 50 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 Ph 3 Sn(HL); however, they do provide significantly better activities than etoposide and cis-platin.

Xueqing Song

Papers

New organotin(IV) derivatives of dipeptides as models for metal–protein interactions: in vitro anti‐tumour activity

Comparative study of structure-activity relationship of di- and tri-organotin(IV) derivatives of amino acid and peptides

Synthesis, structural and larvicidal studies of some triorganotin 2-(p-chlorophenyl)-3-methylbutyrates

New triorganotin(IV) derivatives of dipeptides as anti-inflammatory-antimicrobial agents.

Organotins and quantitative-structure activity/property relationships