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Synthesis and anticancer activity of Pt(II) complexes of spiro-5-substituted 2,4- dithiohydantoins

Despite the widely studied anticancer activity of metal complexes of various hydantoin derivatives, reports on biological properties of dithiohydantoin complexes are limited to only few. Main challenge is determination of their structure, since no crystallographic data are available for metal complexes of dithiohydantoins. Herein, we describe the synthesis and structure of Pt(II) complexes of two spiro-5-(2, 4- dihiohydantoins) with large and potentially intercalating aromatic rings, namely 3′, 4′- dihydro-2H, 2′H, 5H-spiro[imidazolidine-4, 1′- naphthalene]-2, 5-dithione and spiro-(fluorene- 9, 4′-imidazolidine)-2′, 5′-dithione. The anticancer activity of all compounds were tested against HL- 60, BV-173, and K-562 tumor cell lines. Single- crystal X-ray analysis was performed for the spiro-(benzocyclohexane-4′-imidazolidine)-2′, 5′- dithione, whereas all other compounds were characterized by integrated approach of spectroscopic (IR and solid-state NMR) and theoretical (DFT) studies. The analysis of the data suggested Pt2L4 composition of the complexes with bridging N^S coordination of four ligand molecules and two Pt(II) centers of square planar geometry. Polymeric structure in the solid state was also presumed. The complexes showed modest to moderate anticancer activity as compared to cisplatin and the chronic myeloid leukemia derived BV-173 proved to be the most responsive tumor model.

Dithio-hydantoin ; Platinum(II) ; Anticancer activity ; Solid-state NMR ; 13C CPMAS NMR ; DFT calculations ; Single-crystal X-ray data ; Fluorene ; Tetralin

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