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Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies

Basu Baul, Tushar ; Basu, Smita ; de Vos, Dick ; Linden, Anthony

In: Investigational New Drugs, 2009, vol. 27, no. 5, p. 419-431

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    Titre
    • Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies
    Auteur
    • Basu Baul, Tushar. Department of Chemistry, North-Eastern Hill University, NEHU Permanent Campus, Umshing, 793022, Shillong, India
    • Basu, Smita. Department of Chemistry, North-Eastern Hill University, NEHU Permanent Campus, Umshing, 793022, Shillong, India
    • de Vos, Dick. Pharmachemie BV, P.O. Box 552, 2003 RN, Haarlem, The Netherlands
    • Linden, Anthony. Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057, Zurich, Switzerland
    Type de document
    • Postprint
    Langue
    • Anglais
    Publié dans
    • Investigational New Drugs, 2009, vol. 27, no. 5, p. 419-431. Springer US; http://www.springer-ny.com
    Autre version électronique
    Identifiant OAI-PMH
    • oai:doc.rero.ch:314203
    Summary
    Summary: Potassium 2-{[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)]amino}-4-methyl-pentanoate (L1HK) and potassium 2-{[(E)-1-(2-hydroxyphenyl)alkylidene]amino}-4-methyl-pentanoates (L2HK-L3HK) underwent reactions with PhnSnCl4-n (n = 2 and 3) to give the amino acetate functionalized Schiff base organotin(IV) complexes [Ph3SnLH] n (1-3) and [Ph2SnL] (4), respectively. These complexes have been characterized by 1H, 13C, 119Sn NMR, IR spectroscopic techniques in combination with elemental analyses. The crystal structures of 1 and 3 were determined. The crystal structures reveal that the complexes exist as polymeric chains in which the L-bridged Sn-atoms adopt a trans-R3SnO2 trigonal bipyramidal configuration with the Ph groups in the equatorial positions and the axial locations occupied by a carboxylate oxygen atom from one carboxylate ligand and the alcoholic or phenolic oxygen atom of the next carboxylate ligand in the chain. The carboxylate ligands coordinate in the zwitterionic form with the alcoholic/phenolic proton moved to the nearby nitrogen atom. The solution structures were predicted by 119Sn NMR spectroscopy. When these organotin(IV) complexes were tested against A498, EVSA-T, H226, IGROV, M19 MEL, MCF7 and WIDR human tumor cell lines, the average ID50 values obtained were 55, 80 and 35ng/ml for triphenyltin(IV) compounds 1-3, respectively. The most cytotoxic triphenyltin(IV) compound in the present report (3) with an average ID50 value of around 35ng/ml is found to be more cytotoxic for all the cell lines studied than doxorubicin, cisplatin, 5-fluorouracil and etoposide