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Paper | Regular issue | Vol 81, No. 3, 2010, pp.585-600
Published online, 29th December, 2009
DOI: 10.3987/COM-09-11862
Synthesis of Metal Complexes with 1-Substituted 3-Hydroxy-2(1H)-pyridinethiones and Their Insulin-Mimetic Activities

Akira Katoh,* Hiroko Yokoyama, Yuriko Matsumura, Yutaka Yoshikawa, Hiroyuki Yasui, and Hiromu Sakurai

*Department of Materials and Life Science, Faculty of Science and Technology, Seikei University, Musashino-shi, Tokyo 180-8633, Japan


Eight kinds of 1-alkyl-3-hydroxy-2(1H)-pyridinethiones were synthesized from a commercially available 3-methoxy-2(1H)-pyridinone via 3 steps. Zn(II) and vanadyl complexes were synthesized by treatment with Zn(OAc)2 or ZnSO4, and VOSO4, respectively. Vanadyl complexes were found to exist in VO(S2O2) coordination mode by means of ESR spectroscopy. From in vitro evaluation of the inhibitory effect on FFA release from rat adipocytes treated with epinephrine, it was found that IC50 values of Zn(II) complexes with 1-alkyl-3-hydroxy-2(1H)-pyridinethiones, regardless of the methylene-chain length at N-1 position, were in micromolar levels. In other words, these Zn(II) complexes showed higher insulin-mimetic activities than those synthesized previously. On the other hand, the insulin-mimetic activity of vanadyl complexes unfortunately could not be measured owing to their insolubility in KRB buffer which is used in vitro assay.