期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 14, 期 10, 页码 3300-3306出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2005.12.049
关键词
chiral Schiff base; chromium(III); CD spectra; DNA; enantioselective binding
Since conformation of the molecule plays a vital role in the activity of drug, we have investigated the DNA interaction of a chromium(III) complex with ligands in two conformations. Chromium(III) complexes derived from chiral binaphthyl Schiff base ligands, viz. R- and S-2,2'-bis(salicylidencamino) 1,1'-binaphthyl, have been synthesized and characterized by mass, IR, and electronic spectra. The interaction of these R- and S-binaphthyl Schiff base chromium(III) complexes with CT-DNA was investigated with the goal of examining whether the chirality has an influence on the chromium(III)-DNA binding properties. The difference in chirality of the ligand did not show any striking difference in binding properties. The binding constants for R and S conformers were estimated to be 18 (+/- 0.4) x 10(3) and 9.4 (+/- 0.3) x 10(3) M-1, respectively, through spectroscopic titrations. All the experimental results are suggestive that both the isomers are DNA groove binders. The results of steady-state as well as time-resolved fluorescence experiments, however, suggest that the R conformer has restricted mobility when bound to DNA because it is more deeply buried in the groove of DNA compared to the S isomer. (c) 2006 Elsevier Ltd. All rights reserved.
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