SYNTHESIS AND SPECTROSCOPIC CHARACTERIZATION OF DICYCLOHEXYLTIN DERIVATIVES OF DIPEPTIDES, AND INVITRO EFFECTS AGAINST MDA-MB-231 BREAST-CANCER CELLS - CRYSTAL-STRUCTURES OF DICYCLOHEXYLTIN GLYCYLGLYCINATE AND GLYCYLALANINATE

HUBER, F and VORNEFELD, M and PREUT, H and VONANGERER, E and RUISI, G (1992) SYNTHESIS AND SPECTROSCOPIC CHARACTERIZATION OF DICYCLOHEXYLTIN DERIVATIVES OF DIPEPTIDES, AND INVITRO EFFECTS AGAINST MDA-MB-231 BREAST-CANCER CELLS - CRYSTAL-STRUCTURES OF DICYCLOHEXYLTIN GLYCYLGLYCINATE AND GLYCYLALANINATE. APPLIED ORGANOMETALLIC CHEMISTRY, 6 (7). pp. 597-606. ISSN 0268-2605,

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Abstract

Dicyclohexyltin derivatives Cy2SnL (Cy = cyclohexyl) of the dipeptides H2L, glycylglycine, glycylalanine, alanylglycine, glycylvaline, glycylmethionine, glycylphenylalanine and glycyltyrosine, have been obtained by neutralization of Cy2SnO and H2L. The crystal structures of Cy2SnL (L = glycylglycinate, glycylalaninate) have been determined by single X-ray diffraction. Tin in each case has a distorted trigonal bipyramidal environment with the dipeptide acting as a tridentate NNO-ligand. From IR-data, and in some cases from Sn-119 Mossbauer and Sn-119 NMR data, analogous molecular structures are inferred for the other compounds Cy2SnL. Spectroscopic data indicate that the solid-state structures are retained in organic solvents. In vitro tests showed Cy2SnL (H2L = glycylglycine, glycylalanine, alanylglycine, glycylphenylalanine, glycyltyrosine) to exhibit high cytotoxicity against MDA/MB 231 breast cancer cells, while Me2SnL (L = glycylalaninate, glycyltyrosinate, glycyltryptophanate), and R2Snglycylglycinate (R = n-Bu, Ph) proved to be much less active.

Item Type: Article
Uncontrolled Keywords: ANTI-TUMOR ACTIVITY; DIORGANOTIN(IV) COMPLEXES; ORGANOMETALLIC COMPOUNDS; AMINO-ACIDS; MOSSBAUER; DICYCLOHEXYLTIN DIPEPTIDES; DICYCLOHEXYLTIN GLYCYLGLYCINATE; DICYCLOHEXYLTIN GLYCYLALANINATE; CRYSTAL STRUCTURES
Depositing User: Dr. Gernot Deinzer
Last Modified: 19 Oct 2022 08:44
URI: https://pred.uni-regensburg.de/id/eprint/54296

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