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 Hecht, Masayuki Tanno, Shoko Sueyoshi, Naoki Miyata, Haruhiro Okuda, Shunichi Fukuzumi, Nobuo Ikota, Kiyoshi Fukuhara

Research output: Contribution to journalArticle

5 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)3263-3265
Number of pages3
JournalOrganic and Biomolecular Chemistry
Volume3
Issue number18
DOIs
StatePublished - Sep 21 2005
Externally publishedYes

Fingerprint

Gentisates
Salicylic Acid
hydroxyl radicals
Hydroxyl Radical
Antineoplastic Agents
NAD
photochemical reactions
Tumors
pyridines
analogs
Oxidation
acids
oxides
Neoplasms
tumors
oxidation
catechol
2,3-dihydroxybenzoic acid
1-benzyl-1,4-dihydronicotinamide
pyridine N-oxide

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)

Cite this

Nakanishi, I., Nishizawa, C., Ohkubo, K., Takeshita, K., Suzuki, K. T., Ozawa, T., ... Fukuhara, K. (2005). Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue. Organic and Biomolecular Chemistry, 3(18), 3263-3265. https://doi.org/10.1039/b509447j

Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue. / Nakanishi, Ikuo; Nishizawa, Chiho; Ohkubo, Kei; Takeshita, Keizo; Suzuki, Kazuo T.; Ozawa, Toshihiko; Hecht, Sidney; Tanno, Masayuki; Sueyoshi, Shoko; Miyata, Naoki; Okuda, Haruhiro; Fukuzumi, Shunichi; Ikota, Nobuo; Fukuhara, Kiyoshi.

In: Organic and Biomolecular Chemistry, Vol. 3, No. 18, 21.09.2005, p. 3263-3265.

Research output: Contribution to journalArticle

Nakanishi, I, Nishizawa, C, Ohkubo, K, Takeshita, K, Suzuki, KT, Ozawa, T, Hecht, S, Tanno, M, Sueyoshi, S, Miyata, N, Okuda, H, Fukuzumi, S, Ikota, N & Fukuhara, K 2005, 'Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue', Organic and Biomolecular Chemistry, vol. 3, no. 18, pp. 3263-3265. https://doi.org/10.1039/b509447j
Nakanishi I, Nishizawa C, Ohkubo K, Takeshita K, Suzuki KT, Ozawa T et al. Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue. Organic and Biomolecular Chemistry. 2005 Sep 21;3(18):3263-3265. https://doi.org/10.1039/b509447j
Nakanishi, Ikuo ; Nishizawa, Chiho ; Ohkubo, Kei ; Takeshita, Keizo ; Suzuki, Kazuo T. ; Ozawa, Toshihiko ; Hecht, Sidney ; Tanno, Masayuki ; Sueyoshi, Shoko ; Miyata, Naoki ; Okuda, Haruhiro ; Fukuzumi, Shunichi ; Ikota, Nobuo ; Fukuhara, Kiyoshi. / Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue. In: Organic and Biomolecular Chemistry. 2005 ; Vol. 3, No. 18. pp. 3263-3265.
@article{62b2971c558840a59464d2f7340cbf80,
title = "Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue",
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.",
author = "Ikuo Nakanishi and Chiho Nishizawa and Kei Ohkubo and Keizo Takeshita and Suzuki, {Kazuo T.} and Toshihiko Ozawa and Sidney Hecht and Masayuki Tanno and Shoko Sueyoshi and Naoki Miyata and Haruhiro Okuda and Shunichi Fukuzumi and Nobuo Ikota and Kiyoshi Fukuhara",
year = "2005",
month = "9",
day = "21",
doi = "10.1039/b509447j",
language = "English (US)",
volume = "3",
pages = "3263--3265",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "18",

}

TY - JOUR

T1 - Hydroxyl radical generation via photoreduction of a simple pyridine N-oxide by an NADH analogue

AU - Nakanishi, Ikuo

AU - Nishizawa, Chiho

AU - Ohkubo, Kei

AU - Takeshita, Keizo

AU - Suzuki, Kazuo T.

AU - Ozawa, Toshihiko

AU - Hecht, Sidney

AU - Tanno, Masayuki

AU - Sueyoshi, Shoko

AU - Miyata, Naoki

AU - Okuda, Haruhiro

AU - Fukuzumi, Shunichi

AU - Ikota, Nobuo

AU - Fukuhara, Kiyoshi

PY - 2005/9/21

Y1 - 2005/9/21

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=26444499115&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=26444499115&partnerID=8YFLogxK

U2 - 10.1039/b509447j

DO - 10.1039/b509447j

M3 - Article

C2 - 16132086

AN - SCOPUS:26444499115

VL - 3

SP - 3263

EP - 3265

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 18

ER -