Study of the cytotoxic activity of di and triphenyltin(IV) carboxylate complexes

The reaction of 3-methoxyphenyl acetic acid (3-MPAH), 4-methoxyphenylacetic acid (4-MPAH), 2,5-dimethyl-3-furoic acid (DMFUH) or 1,4-benzodioxane-6-carboxylic acid (BZDOH) with triphenyltin(IV) chloride (1:1) or diphenyltin(IV) dichloride (2:1) in the presence Of triethylamine yielded the compounds [SnPh(3)(3-MPA)] (1), [SnPh(3)(4-MPA)] (2), [SnPh(3)(DMFU)] (3), [SnPh(3)(BZDO)] (4), [SnPh(2)(3-MPA)(2)] (5), [SnPh(2)(4-MPA)(2)] (6), [SnPh(2)(DMFU)(2)] (7) and [SnPh(2)(BZDO)(2)](8), respectively. The tetranuclear complex [{Me(2)(DMFU)SnOSn(DMFU)Me(2)}(2)] (9) was prepared by the reaction of dimethyltin(IV) oxide and 2.5-dimethyl-3-furoic acid (DMFUH). The molecular structures of 3, 4 and 9, were determined by X-ray diffraction studies. The cytotoxic activity of the carboxylic acids (3-MPAH, 4-MPAH, BZDOH and DMFUH) and di (5-8) and triphenyltin(IV) complexes (2-4) was tested against tumor cell lines human adenocarcinoma HeLa, human myelogenous leukemia K562, human malignant melanoma Fem-x and normal immunocompetent cells, peripheral blood mononuclear cells PBMC. Triphenyltin(IV) complexes show higher activities than the diphenyltin(IV) derivatives. The most active compound is [SnPh(3)(DMFU)] (3) With IC(50) Value of 0.15 +/- 0.01, 0.051 +/- 0.004, 0.074 +/- 0.004, 0.20 +/- 0.01, 0.15 +/- 0.02 on HeLa, K562, Fem-x, rested and stimulated PBMC, respectively, while the most selective are [SnPh(2)(3-MPA)(2)] (5), [SnPh(2)(DMFU)(2)] (7) and [SnPh(2)(BZDO)(2)] (8). Compounds 3, 5, 7 and 8 present higher activities than cis-platin in all the tested cells and relative high selectivity especially on K562 cells. (C) 2008 Elsevier Inc. All rights reserved.