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Activation Mechanism of N-Nitrosodialkylamine by Reactive Oxygen Species

Research Project

Project/Area Number 23590152
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Environmental pharmacy
Research InstitutionTokyo University of Science

Principal Investigator

MOCHIZUKI Masataka  東京理科大学, 薬学部, 教授 (10072414)

Co-Investigator(Kenkyū-buntansha) INAMI Keiko  東京理科大学, 薬学部, 講師 (00271247)
Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2013: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2012: ¥520,000 (Direct Cost: ¥400,000、Indirect Cost: ¥120,000)
Fiscal Year 2011: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Keywordsニトロソジアルキルアミン / 活性酸素 / 代謝活性化 / フェントン試薬 / 酸化 / 発がん / N-ニトロソジアルキルアミン / ヒドロキシルラジカル / 一酸化窒素 / N-ニトロソジアルキルアミン
Research Abstract

Carcinogenic and mutagenic N-nitroso compounds exist in our environment and can be formed in human body. To elucidate the new activation mechanism of N-nitrosodialkylamines by reactive oxygen species, the reaction mixture with N-nitroso-N-methylpropylamine and Fe2+-Cu2+-H2O2-NO was fractionated, and a direct-acting mutagen which has a ring structure was isolated. It is indicated that N-nitrosodialkylamines was activated by reactive oxygen species via new mechanisms.
Moreover, to clarify the structure-activity relationship for the mutagenesis of the mutagen X derived from N-nitroso-N-methylbutylamine with Fe2+-Cu2+-H2O2-NO, pyrazoline analogues were synthesized and assayed for their mutagenicity in Salmonella typhimurium TA1535. The data showed that the position of N-oxidation in the pyrazoline also affected on the mutagenic activity.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (42 results)

All 2014 2013 2012 2011 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results,  Open Access: 1 results) Presentation (24 results) Book (2 results) Remarks (4 results)

  • [Journal Article] Antimutagenicity screening of extracts from medicinal and edible plants against N-methyl-N-nitroso- urea by the Ames assay2014

    • Author(s)
      J. Tatsuzaki, Y. Jinwei, Y. Kojo, Y. Mine, S. Ishikawa, M. Mochizuki, K. Inami
    • Journal Title

      Genes and Environ

      Volume: (Accepted)

    • NAID

      130004943661

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Assessment of the Antimutagenic Effects of Aqueous Extracts from Herbal Medicines against <i>N</i>-Alkyl-<i>N</i>-nitrosoureas-induced Mutagenicity Using the <i>umu</i> Test2014

    • Author(s)
      K. Inami, M. Takada, K. Itoh, S. Ishikawa, M. Mochizuki
    • Journal Title

      Genes and Environment

      Volume: 36 Issue: 2 Pages: 33-38

    • DOI

      10.3123/jemsge.2014.003

    • NAID

      130004943658

    • ISSN
      1880-7046, 1880-7062
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Antimutagenicity screening of extracts from medicinal and edible plants against N-methyl-N-nitrosourea by the Ames assay2014

    • Author(s)
      J. Tatsuzaki, Y. Jinwei, Y. Kojo, Y. Mine, S. Ishikawa, M. Mochizuki, K. Inami
    • Journal Title

      Genes and Environ.

      Volume: in press

    • NAID

      130004943661

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Transnitrosation of alicyclic N-nitrosamines containing a sulfur atom2013

    • Author(s)
      K. Inami, S. Kondo, Y. Ono, C. Saso, M. Mochizuki
    • Journal Title

      Bioorg. Med. Chem

      Volume: 21 Issue: 24 Pages: 7853-7857

    • DOI

      10.1016/j.bmc.2013.10.008

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Oxidation of <i>N</i>-Alkyl-<i>N</i>-(3-carboxypropyl)nitrosamines by Iron Porphyrin and Oxidant Forms Alkylating Mutagens2013

    • Author(s)
      K. Inami, H. Yasui, H. Tsugumi, S. Ishikawa, M. Mochizuki
    • Journal Title

      Genes and Environment

      Volume: 35 Issue: 4 Pages: 99-104

    • DOI

      10.3123/jemsge.2013.010

    • NAID

      10031196751

    • ISSN
      1880-7046, 1880-7062
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Ruthenium porphyrin and oxidant convert N-nitrosodialkylamines into direct-acting mutagen in the Ames assay2013

    • Author(s)
      K. Inami, K. Yoshimitsu, H. Seino, M. Mochizuki
    • Journal Title

      Toxicol. Res.

      Volume: 2 Issue: 6 Pages: 397-402

    • DOI

      10.1039/c3tx50036e

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] The High Stability of Intermediate Radicals Enhances the Radical-Scavenging Activity of Aminochromanols2012

    • Author(s)
      稲見圭子、中西郁夫、森田海根、古川美礼、大久保敬、福住俊一、望月正隆
    • Journal Title

      RSC Adv

      Volume: 2巻 Issue: 33 Pages: 12714-12717

    • DOI

      10.1039/c2ra21928j

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Chlorine atom substitution infuluences radical scavenging activity of 6-chromanol2012

    • Author(s)
      K. Inami, Y. Ishizuka, M. Furukawa, I. Nakanishi, K. Ohkubo, K. Fukuhara, S. Fukuzumi, M. Mochizuki
    • Journal Title

      Bioorg. Med. Chem

      Volume: 20 Issue: 13 Pages: 4049-4055

    • DOI

      10.1016/j.bmc.2012.05.008

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Structure and mutagenicity of a direct-acting mutagen derived from the reaction of N-nitroso-N-methylbutylamine with hydroxyl radical2012

    • Author(s)
      K. Inami, M. Miura, N. Tsutsumi, E. Okochi, Y. Susaki, S. Ishikawa, S. Motohashi, J. Shiino, K. Takeda, M. Mochizuki
    • Journal Title

      Heterocycles

      Volume: 84 Issue: 2 Pages: 1081-1088

    • DOI

      10.3987/com-11-s(p)90

    • Related Report
      2013 Final Research Report 2012 Research-status Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Isolation and structural identification of a direct-acting mutagen derived from N-nitroso-N-methylpentylamine and Fenton's reagent with copper ion2011

    • Author(s)
      M. Miura, K. Inami, M. Yoshida, K. Yamaguchi, T. Mashino, M. Mochizuki
    • Journal Title

      Bioorg. Med. Chem

      Volume: 19 Issue: 18 Pages: 5693-5697

    • DOI

      10.1016/j.bmc.2011.07.012

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Isolation and structural identification of a direct-acting mutagen derived from N-nitroso- N-methylpentylamine and Fenton’s reagent with copper ion2011

    • Author(s)
      M. Miura, K. Inami, M. Yoshida, K. Yamaguchi, T. Mashino, M. Mochizuki
    • Journal Title

      Bioorg. Med. Chem.

      Volume: 19 Pages: 5693-5697

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] 7-Azabicyclo[2.2.1]heptane as a structural motif to block mutagenicity of nitrosamines2011

    • Author(s)
      T. Ohwada, S. Ishikawa, Y. Mine, K. Inami, T. Yanagimoto, F. Karaki, Y. Kabasawa, Y. Otani, M. Mochizuki
    • Journal Title

      Bioorg. Med. Chem.

      Volume: 19 Pages: 2726-2741

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 還元系シトクロムP450化学モデルによるN-nitrosamineの代謝類似酸化的分解機構2013

    • Author(s)
      中山優, 稲見圭子, 望月正隆
    • Organizer
      日本環境変異原学会第42回大会
    • Place of Presentation
      岡山
    • Related Report
      2013 Final Research Report
  • [Presentation] チオール基あるいはチオアミド基をもつ新規含硫N-ニトロソ化合物の合成と活性評価2013

    • Author(s)
      佐宗千春, 稲見圭子, 望月正隆
    • Organizer
      日本環境変異原学会第42回大会
    • Place of Presentation
      岡山
    • Related Report
      2013 Final Research Report
  • [Presentation] 膀胱発がん性N-butyl-N-(3-carboxypropyl)nitrosami neによるDNA損傷の検出2013

    • Author(s)
      稲見圭子, 望月正隆
    • Organizer
      第72回日本癌学会総会
    • Place of Presentation
      横浜
    • Related Report
      2013 Final Research Report
  • [Presentation] N-ニトロソジアルキルアミンと活性酸素種から生成する直接変異原の構造2013

    • Author(s)
      吉田昌史, 稲見圭子, 望月正隆
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2013 Final Research Report 2012 Research-status Report
  • [Presentation] シトクロムP450化学モデルによるN-ニトロソジアルキルアミンの脱ニトロソ化反応の検討2013

    • Author(s)
      中山優, 稲見圭子, 望月正隆
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2013 Final Research Report 2012 Research-status Report
  • [Presentation] 活性酸素種によるN-ニトロソモルホリンの活性化2013

    • Author(s)
      浅田卓也, 稲見圭子, 望月正隆
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2013 Final Research Report 2012 Research-status Report
  • [Presentation] 膀胱発がん性3-carboxypropylnitrosamine類のDNA相互作用機構の解明2013

    • Author(s)
      安居洸貴, 稲見圭子, 望月正隆
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2013 Final Research Report 2012 Research-status Report
  • [Presentation] 膀胱発がん性N-butyl-N-(3-carboxypropyl)nitrosamineによるDNA損傷の検出2013

    • Author(s)
      稲見 圭子, 望月 正隆
    • Organizer
      第72回 日本癌学会総会
    • Place of Presentation
      横浜
    • Related Report
      2013 Annual Research Report
  • [Presentation] 還元系シトクロムP450化学モデルによるN-nitrosamineの代謝類似酸化的分解機構2013

    • Author(s)
      中山 優, 稲見 圭子, 望月 正隆
    • Organizer
      日本環境変異原学会 第42回大会
    • Place of Presentation
      岡山
    • Related Report
      2013 Annual Research Report
  • [Presentation] チオール基あるいはチオアミド基をもつ新規含硫N-ニトロソ化合物の合成と活性評価2013

    • Author(s)
      佐宗 千春, 稲見 圭子, 望月 正隆
    • Organizer
      日本環境変異原学会 第42回大会
    • Place of Presentation
      岡山
    • Related Report
      2013 Annual Research Report
  • [Presentation] 選択的膀胱発がん性N-ニトロソ化合物の活性化機構2012

    • Author(s)
      安居洸貴, 稲見圭子, 望月正隆
    • Organizer
      日本環境変異原学会第41回大会
    • Place of Presentation
      静岡
    • Related Report
      2013 Final Research Report
  • [Presentation] 活性酸素種によるN-ニトロソジアルキルアミンの変異原性発現機構2012

    • Author(s)
      吉田昌史, 稲見圭子, 望月正隆
    • Organizer
      日本環境変異原学会第41回大会
    • Place of Presentation
      静岡
    • Related Report
      2013 Final Research Report
  • [Presentation] 活性酸素種による環状N-ニトロソ化合物の活性化2012

    • Author(s)
      浅田卓也, 稲見圭子, 望月正隆
    • Organizer
      日本環境変異原学会第41回大会
    • Place of Presentation
      静岡
    • Related Report
      2013 Final Research Report
  • [Presentation] 還元系シトクロムP450化学モデル系によるN–ニトロソジアルキルアミンの脱ニトロソ化2012

    • Author(s)
      中山優, 稲見圭子, 望月正隆
    • Organizer
      日本環境変異原学会第41回大会
    • Place of Presentation
      静岡
    • Related Report
      2013 Final Research Report
  • [Presentation] 活性酸素種によるN-ニトロソジアルキルアミンの新規活性化機構2012

    • Author(s)
      吉田昌史, 稲見圭子, 望月正隆
    • Organizer
      第71回日本癌学会総会
    • Place of Presentation
      札幌
    • Related Report
      2013 Final Research Report
  • [Presentation] 1-ピラゾリンに対する位置選択的N-オキシド化の検討2012

    • Author(s)
      松居久美子,三浦基文,鳥山正晴,本橋重康,吉田昌史,稲見圭子,望月正隆
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Related Report
      2013 Final Research Report 2011 Research-status Report
  • [Presentation] ルテニウムポルフィリン・酸化剤のシトクロムP450化学モデルによるN-ニトロソ化合物の変異原性発現機構2012

    • Author(s)
      情野秀晃,稲見圭子,望月正隆
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Related Report
      2013 Final Research Report 2011 Research-status Report
  • [Presentation] アルキルチオアミド基を導入した五員環含硫N-ニトロソ化合物の合成とニトロソ基移動能2012

    • Author(s)
      小野裕太,稲見圭子,望月正隆
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Related Report
      2013 Final Research Report
  • [Presentation] 活性酸素種によるN-ニトロソジアルキルアミンの新規活性化機構2012

    • Author(s)
      吉田 昌史, 稲見 圭子, 望月 正隆
    • Organizer
      第71回 日本癌学会総会
    • Place of Presentation
      札幌
    • Related Report
      2012 Research-status Report
  • [Presentation] 活性酸素種によるN-ニトロソジアルキルアミンの変異原性発現機構2012

    • Author(s)
      吉田 昌史, 稲見 圭子, 望月 正隆
    • Organizer
      日本環境変異原学会 第41回大会
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report
  • [Presentation] 選択的膀胱発がん性N-ニトロソ化合物の活性化機構2012

    • Author(s)
      安居 洸貴, 稲見 圭子, 望月 正隆
    • Organizer
      日本環境変異原学会 第41回大会
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report
  • [Presentation] 活性酸素種による環状N-ニトロソ化合物の活性化2012

    • Author(s)
      浅田 卓也, 稲見 圭子, 望月 正隆
    • Organizer
      日本環境変異原学会 第41回大会
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report
  • [Presentation] N-ニトロソジアルキルアミンと活性酸素種により生じる変異原物質の活性発現機構の解明2011

    • Author(s)
      吉田昌史, 稲見圭子, 望月正隆
    • Organizer
      日本環境変異原学会 第40回大会
    • Place of Presentation
      東京
    • Related Report
      2011 Research-status Report
  • [Presentation] ルテニウムポルフィリン錯体/酸化剤によるN-ニトロソジアルキルアミンの変異原性発現機構の解明2011

    • Author(s)
      情野秀晃, 稲見圭子, 望月正隆
    • Organizer
      日本環境変異原学会 第40回大会
    • Place of Presentation
      東京
    • Related Report
      2011 Research-status Report
  • [Book] 有機化学の基礎2013

    • Author(s)
      望月正隆, 稲見圭子
    • Publisher
      東京化学同人 (東京)
    • Related Report
      2013 Final Research Report
  • [Book] ベーシック薬学教科書シリーズ無機化学2011

    • Author(s)
      稲見圭子, 望月正隆, 青木伸編
    • Publisher
      化学同人 (京都)
    • Related Report
      2013 Final Research Report
  • [Remarks] 東京理科大学ホームページ

    • URL

      http://www.tus.ac.jp

    • Related Report
      2013 Final Research Report
  • [Remarks] http://www.tus.ac.jp/

    • Related Report
      2013 Annual Research Report
  • [Remarks] 東京理科大学

    • URL

      http://www.tus.ac.jp/

    • Related Report
      2012 Research-status Report
  • [Remarks]

    • URL

      https://ridai.admin.tus.ac.jp/ridai/doc/ji/RIJIA01.php

    • Related Report
      2011 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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