Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 22, Issue 23, Pages 7056-7059Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2012.09.087
Keywords
Berberine; Carboxylate; Copper(II) complex; Synthesis; DNA cleavage
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Funding
- National Natural Science Foundation of China [21102070]
- Program for New Century Excellent Talents in University [NCET-11-0920]
- Program for Pearl River New Stars of Science and Technology in Guangzhou [2011J2200071]
- Department of Education of Guangdong Province
- Guangdong Provincial Department of Science and Technology of China [2012B050100007]
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9-O-(4-carboxybenzyl)berberine (CBB) 1 was synthesized from the reaction of berberrubine with methyl 4-(bromomethyl)benzoate and subsequent hydrolysis. Its Cu(II) complex 2 was prepared from the reaction with Cu(NO3)(2)center dot 3H(2)O, and established as [Cu(CBB)(2)](NO3)(2)center dot 2H(2)O by means of H-1 NMR, UV, IR, elemental analysis and TGA measurements. Agarose gel electrophoresis study on the cleavage of plasmid pBR322 DNA indicated that complex 2 was capable of efficiently cleaving DNA under physiological conditions, most probably via an oxidative mechanistic pathway involving the formation of singlet oxygen as the reactive species. Kinetic assay afforded the maximal first-order rate constant k(max) of 2.41 h (1) and Michaelis constant K-M of 2.64 mM, respectively, representing ca. 10(8)-fold acceleration in the cleavage. This catalytic efficacy is attributed to the Cu(II)-assisted formation of dimeric species, in which the two berberine subunits cooperatively bind to DNA, whereas the carboxylate-coordinated Cu(II) moiety functions as the cleavage-active center. (C) 2012 Elsevier Ltd. All rights reserved.
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