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Mechanism of DNA damaging by photo- and metabolic products of carcinogenic ethylbenzene

Research Project

Project/Area Number 16590097
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Environmental pharmacy
Research InstitutionMeijo University

Principal Investigator

KOJIMA Nakao  Meijo University, Faculty of Pharmacy, Professor, 薬学部, 教授 (80333178)

Co-Investigator(Kenkyū-buntansha) KAWANISHI Shosuke  Mie University, Department of Medicine, Professor, 医学部, 教授 (10025637)
HASHIZUME Kiyomatsu  Meijo University, Faculty of Pharmacy, Assistant Professor, 薬学部, 助教授 (50076733)
TODA Chitose  Meijo University, Faculty of Pharmacy, Assistant, 薬学部, 助手 (00076738)
UEDA Koji  Meijo University, Faculty of Pharmacy, Assistant, 薬学部, 助手 (30351092)
Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 2005: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2004: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsEnvironmental chemicals / DNA damage / VOC / ROS / 8-oxodG / Structure-activity relationship / light irradiation / metabolic activation / 光照射 / 代謝活性化 / 化学発がん / 酸化的遺伝子損傷 / 酸化還元サイクル / 活性酸素種 / 光活性化 / エチルベンゼン / 光分解 / 肝ミクロソーム / P450
Research Abstract

Ethylbenzene is an air pollutant detected often in the environment. Ethylbenzene is a non-mutagenic carcinogen and its carcinogenesis mechanism is not elucidated. In this research, we showed that ethylbenzene transformed into genotoxic by light exposure or metabolism. Its underlying mechanism involves peroxiethylbenzene and ethyl catechol/hydroquinone, which generates reactive oxygen species in their redox reaction with Cu and damages DNA especially at 5' of consecutive guanine. We expanded this mechanism to other several environmental chemicals that follows. 1)Nonylphenol, a government-certified endocrine disruptor turned to be genotoxic by light irradiation. 2)Methyl paraben, a widely used preservative, was activated by the combination of light and metabolism. 3)An additional functional group suppressed DNA damage of catechol. This structure-activity relationship is useful to predict the risk of chemicals. The key structure for DNA damaging activity is aromatic hydroxylation and this is important for other activities such as endocrine disruption. 4)Plasticizers revealed its potential estrogenic activity after sunlight exposure. 5)Sunscreens generated hydroxyl radical and activated themselves by sunlight irradiation. 6)A specific hydroxylation made flavonoides highly anti-estrogenic. As stated above, this study provided many important findings for risk assessment of environmental chemicals.

Report

(3 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • Research Products

    (19 results)

All 2006 2005 2004

All Journal Article (19 results)

  • [Journal Article] 環境化学物質の活性化による毒性発現2006

    • Author(s)
      小嶋 仲夫
    • Journal Title

      名状大学総合学術研究所紀要 11(印刷中)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Formation of estrogenic products from environmental phthalate esters under light exposure.2006

    • Author(s)
      Okamoto et al.
    • Journal Title

      Chemosphere 64(In press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Formation of DNA damaging product from light-irradiated nonylphenol.2006

    • Author(s)
      Okamoto et al.
    • Journal Title

      J. Health Sci. 52

      Pages: 91-95

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Anti-estrogenic activity of prenylated isoflavones from Millettia pachycarpa : implications for pharmacophores and unique mechanisms.2006

    • Author(s)
      Okamoto et al.
    • Journal Title

      J. Health Sci. 52

      Pages: 186-191

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Activation of chemicals in the environment.2006

    • Author(s)
      Kojima
    • Journal Title

      Bul.Res.Inst.(Meijo Univ.) 11 (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Formation of estrogenic products from environmental phthalate esters under light exposure.2006

    • Author(s)
      Okamoto et al.
    • Journal Title

      Chemosphere 64 (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Formation of DNA damaging product from light-irradiated Nonylphenol.2006

    • Author(s)
      Okamoto et al.
    • Journal Title

      J.Health Sci. 52

      Pages: 91-95

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Anti-estrogenic activity of prenylated isoflavones from Millettia pachycarpa : implications for pharmacophores and unique mechanisms.2006

    • Author(s)
      Okamoto et al.
    • Journal Title

      J.Health Sci. 52

      Pages: 186-191

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Formation of DNA damaging product from light-irradiated nonylphenol2006

    • Author(s)
      Okamoto et al.
    • Journal Title

      J.Health Sci. 52

      Pages: 91-95

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Isoflavonoids with antiestrogenic activity from Millettia pachycarpa2006

    • Author(s)
      Ito et al.
    • Journal Title

      J.Nat.Prod. 96

      Pages: 138-141

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Formation of estrogenic products from environmental phthalate esters under light exposure2006

    • Author(s)
      Okamoto et al.
    • Journal Title

      Chemosphere (in press)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Anti-estrogenic activity of prenylated isoflavones from Millettia pachycarpa : implications for pharmacophores and unique mechanisms2006

    • Author(s)
      Okamoto et al.
    • Journal Title

      J.Health Sci. 52(2)(in press)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Isolation of Phthalate ester-degradable bacteria from river water by acclimation to di-n-butyl phthalate or mono-n-butyl phthalate2005

    • Author(s)
      Oyama et al.
    • Journal Title

      J.Res.Inst.Meijo Univ. 4

      Pages: 73-78

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Metabolic activation of carcinogenic ethylbenzene leads to oxidative DNA damage.2004

    • Author(s)
      Midorikawa et al.
    • Journal Title

      Chem. Biol. Interact. 150

      Pages: 271-281

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Metabolic activation of carcinogenic ethylbenzene leads to oxidative DNA damage.2004

    • Author(s)
      Midrikawa et al.
    • Journal Title

      Chem.Biol.Interact. 150

      Pages: 271-281

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Metabolic activation of carcinogenic ethylbenzene leads to oxidative DNA damage2004

    • Author(s)
      Midorikawa et al.
    • Journal Title

      Chem.Biol.Interact. 150

      Pages: 271-281

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Unequivocal estrogen receptor-binding affinity of phthalate esters featured with ring hydroxylation and proper alkyl chain size.2004

    • Author(s)
      Toda et al.
    • Journal Title

      Arch.Biochem.Biophys. 431

      Pages: 16-21

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Novel estrogenic microsomal metabolites from phthalate esters.2004

    • Author(s)
      Okamoto et al.
    • Journal Title

      J.Health Sci. 50

      Pages: 556-560

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Products variation of phthalate esters in environmental biodegradation.2004

    • Author(s)
      Okamoto et al.
    • Journal Title

      J.Res.Inst.Meijo Univ. 3

      Pages: 77-83

    • Related Report
      2004 Annual Research Report

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Published: 2004-04-01   Modified: 2016-04-21  

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