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

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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 35 ng/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 35 ng/ml is found to be more cytotoxic for all the cell lines studied than doxorubicin, cisplatin, 5-fluorouracil and etoposide.

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Acknowledgements

The financial support of the Department of Science & Technology, New Delhi, India (Grant No.SR/S1/IC-03/2005,TSBB) and the University Grants Commission, New Delhi, India through SAP-DSA, Phase-III, are gratefully acknowledged. The in vitro cytotoxicity experiments were carried out by Ms. P. F. van Cuijk in the Laboratory of Translational Pharmacology, Department of Medical Oncology, Erasmus Medical Center, Rotterdam, The Netherlands, under the supervision of Dr. E. A. C. Wiemer and Prof. Dr. G. Stoter.

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  1. Department of Chemistry, North-Eastern Hill University, NEHU Permanent Campus, Umshing, Shillong, 793022, India

    Tushar S. Basu Baul & Smita Basu

  2. Pharmachemie BV, P.O. Box 552, 2003 RN, Haarlem, The Netherlands

    Dick de Vos

  3. Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057, Zurich, Switzerland

    Anthony Linden

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  1. Tushar S. Basu Baul
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Correspondence to Tushar S. Basu Baul or Anthony Linden.

Appendix

Appendix

Supplementary Material

CCDC-696775 and CCDC-696776 contain the supplementary crystallographic data for complexes 1 and 3, respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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Basu Baul, T.S., Basu, S., de Vos, D. et al. Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies. Invest New Drugs 27, 419–431 (2009). https://doi.org/10.1007/s10637-008-9189-1

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