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Synthesis of NO generating compounds with hydroxyl releasing ability

Research Project

Project/Area Number 12672170
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 医薬分子機能学
Research InstitutionNational Institute of Health Sciences (NIHS)

Principal Investigator

TANNO Masayuki (2001)  National Institute of Health Sciences, Div. of Org., Senior Researcher, 有機化学部, 主任研究官 (60171914)

末吉 祥子 (2000)  国立医薬品食品衛生研究所, 有機化学部, 室長 (80171114)

Co-Investigator(Kenkyū-buntansha) MIYATA Naoki  National Institute of Health Sciences, Div. of Org., Head, 有機化学部, 部長 (50114674)
FUKUHARA Kiyoshi  National Institute of Health Sciences, Div. of Org., Section Chief, 有機化学部, 室長 (70189968)
丹野 雅幸  国立医薬品食品衛生研究所, 有機化学部, 主任研究官 (60171914)
Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2001: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2000: ¥2,500,000 (Direct Cost: ¥2,500,000)
KeywordsNitric Oxide / Hydroxyl / Nitosamine / Amidoxime / グルコースオキシダーゼ / ヒドロキシルラジカル / ニトロソアミン / DNA切断活性
Research Abstract

Nitric oxide (NO) is an important bioregulatory molecule responsible for endothelium-derived relaxaoon. NO reacts with a superoxide radical anion which is called active oxygen to give a peroxymtnte. However, there are many points to be indistinct aboout the influence of the same active, ve oxygen species, a hydroxy radical (hydroxyl). In the purpose of clearing this, we have developed the NO generating compounds with hydroxyl releasing ability
1.Synthesis of aromatic N-nitrosamines : We synthesized several aromatic compounds having both N-nitroso and N-oxido groups. Phenylpyridylnitrosamines were prepared by nitrosation of the corespondmg amines with sodium nitrite in formic acid.
2.Synthesis of amidoximes and hydroxyguanidines : We also synthesized several compounds having an N-hydroxyamidino group which is a partial structure of N-hydroxy-L-arginine which is a key intermediate in the biosynthesis of NO from L-arginine. Amidoximes and hydroxyguanidines were prepared by the reaction of the corresponding nitrites with hydroxylamine in dioxane.
3.Determination of NO and hydroxyl : Nitrosamines generated NO and hydroxyl by light irradiation and these radicals were detected in ESR spectroscopy. The quantity of NO was measured using the Griess-Saltzman method. Amidoxime derivatives released NO when they were oxidized with Fenton reagent. In case of amidoxime N-oxide derivatives, NO was produced by the reacton with glucoseoxidase in the presence of glucose and Fe(II) under anaerobic conditions
Now synthesized compounds will be useful for the chemical and biochemical research of the action of NO with active oxygen species.

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (8 results)

All Other

All Publications (8 results)

  • [Publications] 丹野雅幸, 末吉祥子, 宮田直樹: "NOドナー"国立衛研報. 118. 21-36 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] I.Nakanishi, K.Fukuhara, et al.: "Superoxide anion generation via electron-transfer oxidation of catechin dianion by molecular oxygen in an aprotic medium"Chem. Lett.. 1152-1153 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Fukuhara, M.Kurihara, N.Miyata: "Photochemical generation of nitric oxide from 6-nitrobenzo[a]pyrene"J. Am. Chem. Soc. 123. 8662-8666 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 丹野雅幸, 宮田直樹 他: "生体内一酸化窒素(NO)実験プロトコール:NOドナー"共立出版. 288 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Tanno. S. Sueyoshi and N. Miyata: "Nitric Oxide (NO) Donor"Bull. NatL Inst. Health Sci.. 118. 21-36 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] I. Nakanishi, K. Fukuhara, K. Ohkubo, T. Shimada, H. Kansui, M. Kurihara, S, Urano, S. Fukuzumi and N. Miyata Naoki Miyata: "Superoxide anion generation via electron-transfer oxidation of catechin dianion by molecular oxygen in an aprotic medium"Chem. Lett. 1152-1153 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Fukuhara, M. Kurihara, and N. Miyata: "Photochemical generation of nitric oxide from 6-nitrobenzo[a]pyrene"J. Am. Chem. Soc. 123. 8662-8666 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Fukuhara, etc.: "Photochemical generation of nitric oxide from 6-nitrobenzo[a]pyrene"J. Am. Chem. Soc.. 123. 8662-8666 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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