Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue

Ikuo Nakanishi; Chiho Nishizawa; Kei Ohkubo; Keizo Takeshita; Kazuo T. Suzuki; Toshihiko Ozawa; Sidney M. Hecht; Masayuki Tanno; Shoko Sueyoshi; Naoki Miyata; Haruhiro Okuda; Shunichi Fukuzumi; Nobuo Ikota; Kiyoshi Fukuhara

doi:10.1039/B509447J

Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue†

Ikuo Nakanishi,*^ab Chiho Nishizawa,^ac Kei Ohkubo,^b Keizo Takeshita,^d Kazuo T. Suzuki,^c Toshihiko Ozawa,^a Sidney M. Hecht,^e Masayuki Tanno,^f Shoko Sueyoshi,^f Naoki Miyata,^g Haruhiro Okuda,^f Shunichi Fukuzumi,^b Nobuo Ikota*^a and Kiyoshi Fukuhara*^f

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* Corresponding authors

^a Redox Regulation Research Group, Research Center for Radiation Safety, National Institute of Radiological Sciences (NIRS), Inage-ku, Chiba, Japan
E-mail: nakanis@nirs.go.jp
Fax: +81 43 255 6819
Tel: +81 43 206 3131

^b Department of Material and Life Science, Graduate School of Engineering, Osaka University, SORST, Japan Science and Technology Agency (JST), Suita, Osaka, Japan
E-mail: fukuzumi@chem.eng.osaka-u.ac.jp
Fax: +81 6 6879 7370
Tel: +81 6 6879 7368

^c Department of Toxicology and Environmental Health, Graduate School of Pharmaceutical Science, Chiba University, Chuo-ku, Chiba, Japan

^d Faculty of Pharmaceutical Sciences, Sojo University, Ikeda, Kumamoto, Japan

^e Department of Chemistry and Biology, University of Virginia, Charlottesville, Virginia, USA

^f Division of Organic Chemistry, National Institute of Health Sciences (NIHS), Setagaya-ku, Tokyo, Japan
E-mail: fukuhara@nihs.go.jp
Fax: +81 3 3707 6950
Tel: +81 3 3700 1141

^g Graduate School of Pharmaceutical Sciences, Nagoya City University, Mizuho-ku, Nagoya, Aichi, Japan

Abstract

Photoreduction of pyridine N-oxide, which has a key structure of antitumor agents for hypoxic solid tumors, by 1-benzyl-1,4-dihydronicotinamide in deaerated aprotic media resulted in generation of hydroxyl radical, leading to the oxidation of salicylic acid to 2,3- and 2,5-dihydroxybenzoic acids, and catechol.

Organic & Biomolecular Chemistry

Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue†

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Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue

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