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Synthesis and insulin-mimetic activities of metal complexes with 3-hydroxypyridine-2-carboxylic acid

TitleSynthesis and insulin-mimetic activities of metal complexes with 3-hydroxypyridine-2-carboxylic acid
Publication TypeJournal Article
Year of Publication2005
AuthorsNakai, M, Sekiguchi, F, Obata, M, Ohtsuki, C, Adachi, Y, Sakurai, H, Orvig, C, Rehder, D, Yano, S
JournalJournal of Inorganic Biochemistry
Volume99
Pagination1275-1282
Date PublishedJun
Type of ArticleArticle
ISBN Number0162-0134
Keywords3-hydroxypyridine-2-carboxylic acid (H(2)hpic), CHEMISTRY, DIABETIC-RATS, GLUCOSE, insulin-mimetic drug, MECHANISM, MONONUCLEAR, RAT ADIPOCYTES, VANADIUM
Abstract

Metal complexes of 3-hydroxypyridine-2-carboxylic acid (H(2)hpic), [Co(Hhpic)(2)(H2O)(2)] (1), [Fe(Hhpic)(2)(H2O)(2)] (2), [Zn(Hhpic)(2)(H2O)(2)] (3), [Mn(Hhpic)(2)(H2O)(2)] (4), and [Cu(Hhpic)(2)] (5) have been synthesized and characterized by mass spectrometry, elemental analysis, magnetic susceptibility, infrared, electronic absorption and electron paramagnetic resonance (EPR) spectroscopies. The solid-state structure of 1 has been established by X-ray crystallography. The EPR spectra of 4 and 5 displayed six and four-line hyperfine splitting patterns, respectively, due to coupling of the unpaired electron with the Mn-55 (I=5/2) nucleus and the Cu-63 (I=3/2) nucleus. In the EPR spectrum of 5, an additional five-line super-hyperfine splitting pattern was observed at 77 K, caused by additional interaction of the unpaired electron with ligand nitrogen atoms (I=1), indicating that the structure of 5 was retained in dimethyl sulfoxide solution. The insulin-mimetic activity of these complexes was evaluated by means of in vitro measurements of the inhibition of free fatty acid (FFA) release from epinephrine-treated, isolated rat adipocytes. Complex 5 was found to exhibit the most potent insulin-mimetic activity among the complexes examined in this study. (C) 2005 Elsevier Inc. All rights reserved.

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