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Toxic mechanisms and metabolism of endogenous and exogenous AhR ligands

Research Project

Project/Area Number 16201012
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Risk sciences of radiation/Chemicals
Research InstitutionKyoto University

Principal Investigator

MATSUI Saburo  Kyoto Univ., Global Environmental Studies, Professor, 地球環境学堂, 教授 (90092808)

Co-Investigator(Kenkyū-buntansha) MATSUDA Tomonari  Kyoto Univ., Global Environmental Studies, Assoc.Prof., 地球環境学堂, 助教授 (50273488)
NAKAYAMA Aki  Kyoto Univ., Engineering, Research Associate, 工学研究科, 助手 (10335200)
Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥49,530,000 (Direct Cost: ¥38,100,000、Indirect Cost: ¥11,430,000)
Fiscal Year 2005: ¥17,160,000 (Direct Cost: ¥13,200,000、Indirect Cost: ¥3,960,000)
Fiscal Year 2004: ¥32,370,000 (Direct Cost: ¥24,900,000、Indirect Cost: ¥7,470,000)
KeywordsArylhydrocarbon Receptor (AhR) / Indirubin / Indole compounds / dye / dioxin / AhR / LC / MS / 多環芳香族化合物
Research Abstract

Arylhydrocarbon Receptor (AhR) recognizes wide variety of chemicals as its ligand. It is widely known that many persistent organic pollutants (POPs) such as polychlorinated dibenzo-dioxins (PCDDs), polychlorinated dibenzo-furans (PCDFs), polychlorinated biphenyls (PCBs) and polyaromatic hydrocarbons (PAHs) are AhR ligands. It is also known that some natural indole compounds, such as indole[3,2-b]carbazole (ICZ), 3,3'-diindolylmethane (DIM), 6-folmylindolo [3,2-b]carbazole (FICZ) show strong AhR ligand activity. Our group also has found one of the strongest AhR ligand, indirubin. In this study, we detected and identified the new AhR ligands in the environment and in food. We identified several AhR ligands in the effluent from dye works and a municipal waste water treatment plant. Those AhR lingads were dyes which are widely used. We showed AhR ligand activity in several commercially obtained anthraquinone dyes. We also found that there were several AhR ligands in coffee extract.
We compared the activity of several natural AhR ligands, DIM,ICZ,FICZ and indirubin. ICZ,FICZ and indirubin all showed very strong activity. However, the activity was vanished when they were incubated with CYP1A1 or CYP1A2,which are the monooxigenases induced via AhR signaling. The difference of toxicity between these natural ligands and dioxins may be due to their metabolic propaties.

Report

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

    (38 results)

All 2006 2005 2004 Other

All Journal Article (35 results) Book (3 results)

  • [Journal Article] Detection and Identification of Dyes Showing AhR Binding Affinity in Treated Sewage Effluents2006

    • Author(s)
      P.Chou, S.Matsui, T.Matsuda
    • Journal Title

      Wat. Sci. Tech (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] 「AhRの内因性リガンド』-外因性リガンド多環芳香族と内因性リガンド-インディゴ・インディルビン-2006

    • Author(s)
      松井三郎, 松田知成, 足立淳, 三崎健太郎
    • Journal Title

      ホルモンと臨床 54

      Pages: 41-46

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] NAPL affects on benzo〔a〕pyrene biodegradation in soil by the indigenous microbiota and through bioaumentation2006

    • Author(s)
      R.Kanaly, HG.Hur, K.Watanabe
    • Journal Title

      Wat. Sci. Tech (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] Arylhydrocarbon receptor ligand acitivity of indirubin2006

    • Author(s)
      T.Matsuda, J.Adachi
    • Journal Title

      Indirubin, the red shade of indigo (Life in Progress Editions, Roscoff, France)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] 「AhRの内因性リガンド」-外因性リガンド多環芳香族と内因性リガンド-インディゴ・イン2006

    • Author(s)
      松井三郎, 松田知成, 足立淳, 三崎健太郎
    • Journal Title

      ホルモンと臨床 54

      Pages: 41-46

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Isolation and Identification of a New AhR Ligand 3' - Hydroxybenzo〔b〕quinophthalone in Dyeing Wastewater2005

    • Author(s)
      P.Chou, S.Matsui, K.Misaki, T.Matsuda
    • Journal Title

      Organohalogen Compounds 67(CD-ROM)

      Pages: 1746-1746

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A natural ary1 hydrocarbon receptor ligand, indirubin, causes the p21 (waf1/cip1) up-regulation cooperated with tumor necrosis factor-alpha2005

    • Author(s)
      H.Kaji, Y.Kida, J.Adachi, S.Matsui et al.
    • Journal Title

      Organohalogen Compounds 67(CD-ROM)

      Pages: 745-745

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Characterization of polycyclic aromatic hydrocarbons (PAHs) in different size fractions in deposited road particles (DRPs) from Lake Biwa area, Japan2005

    • Author(s)
      Lee BC, Shimizu Y, Masuda T, Matsui S
    • Journal Title

      Environ. Sci. Technol 39

      Pages: 7402-7409

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Characterization of the first flush in storm water runoff from an urban roadway2005

    • Author(s)
      Lee BC, Matsui S, Shimizu Y, Masuda T
    • Journal Title

      Environ. Technol 26

      Pages: 773-782

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] 4-oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation, causes DNA adduct formation in mouse organs2005

    • Author(s)
      H.Kasai et al.
    • Journal Title

      Industrial Health 43(4)

      Pages: 699-701

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A new installation for treatment of road runoff : up-flow filtration by porous polypropylene media2005

    • Author(s)
      3.BC.Lee, S.Matsui, Y.Shimizu, T.Matsuda, Y.Tanaka
    • Journal Title

      Wat. Sci. Tech. 52(12)

      Pages: 225-232

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A new installation for treatment of road runoff : up-flow filtration by porous polypropylene media,2005

    • Author(s)
      BC.Lee et al.
    • Journal Title

      Wat.Sci.Tech. 52(12)

      Pages: 225-232

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] 4-oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation, causes DNA adduct formation in mouse organs,2005

    • Author(s)
      H.Kasai et al.
    • Journal Title

      Industrial Health 43(4)

      Pages: 699-701

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Characterizations of the first flush in storm water runoff from an urban roadway,2005

    • Author(s)
      BC.Lee et al.
    • Journal Title

      Environ.Technol. 26(7)

      Pages: 773-782

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Isolation and Identification of a New AhR Ligand 3'-Hydroxybenzo[b]quinophthalone in Dyeing Wastewater2005

    • Author(s)
      P.Chou, S.Matsui, K.Misaki, T.Matsuda
    • Journal Title

      Organohalogen Compounds 67(CD-ROM)

      Pages: 1746-1746

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A natural aryl hydrocarbon receptor ligand, indirubin, causes the p21 (waf1/cip1) up-regulation cooperated with tumor necrosis factor-alpha2005

    • Author(s)
      H.Kaji, Y.Kida, J.Adachi, S.Matsui et al.
    • Journal Title

      Organohalogen Compounds 67(CD-ROM)

      Pages: 745-745

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Detection and Identification of Dyes Showing AhR Binding Affinity in Treated Sewage Effluents2005

    • Author(s)
      P.Chou, S.Matsui, T.Matsuda
    • Journal Title

      Proceedings of IWA international Conference "Chemical Industries 2005" (CD-ROM)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Characterization of polycyclic aromatic hydrocarbons (PAHs) in different size fractions in deposited road particles (DRPs) from Lake Biwa area, Japan2005

    • Author(s)
      Lee BC, Shimizu Y, Matsuda T, Matsui S
    • Journal Title

      Environ.Sci.Technol 39

      Pages: 7402-7409

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Characterizations of the first flush in storm water runoff from an urban roadway2005

    • Author(s)
      Lee BC, Matsui S, Shimizu Y, Matsuda T
    • Journal Title

      Environ.Technol. 26

      Pages: 773-782

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Detection of Genistein as an Estrogenic Contaminant of River Water in Osaka2004

    • Author(s)
      M.Kawanishi et al.
    • Journal Title

      Environ, Sci. Technol. 38

      Pages: 6424-6429

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Translesion Synthesis past 2' -Deoxyxanthosine, a Nitric Oxide-derived DNA Adduct, by Mammalian DNA Polymerases2004

    • Author(s)
      M.Yasui et al.
    • Journal Title

      J. Mol. Biol. 344

      Pages: 665-674

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Ary1 hydrocarbon receptor-mediated induction of microsomal drug-metabolizing enzyme activity by indirubin2004

    • Author(s)
      K.Sugihara et al.
    • Journal Title

      Biochem. Biophys. Res. Commun. 318

      Pages: 571-578

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Analysis of Estrogen-Like Compounds in the Environment by High Performance Liquid Chromatography Bioassay2004

    • Author(s)
      S.Iwasaki et al.
    • Journal Title

      Journal of Bioscience and Bioengineering 97(3)

      Pages: 216-218

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Comparison of Gene Expression Patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a Natural Arylhydrocarbon2004

    • Author(s)
      ll.J.Adachi, Y.Mori, S.Matsui, T.Matsuda
    • Journal Title

      Toxicol. Sci. 80

      Pages: 161-169

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] DNA付加体の分析方法-LC/ESI/MS/MSはポストラベルを越えたか?2004

    • Author(s)
      松田知成
    • Journal Title

      環境変異原研究 26

      Pages: 199-201

    • NAID

      110001713952

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Detection of Genistein as an Estrogenic Contaminant of River Water in Osaka2004

    • Author(s)
      M.Kawanishi et al.
    • Journal Title

      Environ.Sci.Technol. 38

      Pages: 6424-6429

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Translesion Synthesis past 2'-Deoxyxanthosine, a Nitric Oxide-derived DNA Adduct, by Mammalian DNA Polymerases2004

    • Author(s)
      M.Yasui et al.
    • Journal Title

      J.Mol.Biol. 344

      Pages: 665-674

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Aryl hydrocarbon receptor-mediated induction of microsomal drug-metabolizing enzyme activity by indirubin and indigo2004

    • Author(s)
      K.Sugihara et al.
    • Journal Title

      Biochem.Biophys.Res.Commun. 318

      Pages: 571-578

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Analysis of Estrogen-Like Compounds in the Environment by High Performance Liquid Chromatography Bioassay,2004

    • Author(s)
      S.Iwasaki et al.
    • Journal Title

      Journal of Bioscience and Bioengineering 97(3)

      Pages: 216-218

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Comparison of Gene Expression Patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a Natural Arylhydrocarbon Receptor Ligand, Indirubin2004

    • Author(s)
      J.Adachi et al.
    • Journal Title

      Toxicol.Sci. 80

      Pages: 161-169

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Detection of Genistein as an Estrogenic Contaminant of River Water in Osaka2004

    • Author(s)
      M.Kawanishi, et al.
    • Journal Title

      Environ. Sci. Technol. 38

      Pages: 6424-6429

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Aryl hydrocarbon receptor-mediated induction of microsomal drug-metabolizing enzyme activity by indirubin and indigo2004

    • Author(s)
      K.Sugihara, et al.
    • Journal Title

      Biochem. Biophys. Res. Commun. 318

      Pages: 571-578

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Comparison of Gene Expression Patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a Natural Arvlhvdrocarbon Receptor Ligand, Indirubin2004

    • Author(s)
      J.Adachi, Y.Mori, S.Matsui, T.Matsuda
    • Journal Title

      Toxicol.Sci. 80

      Pages: 161-169

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Detection and identification of dyes showing AhR binding affinity in treated sewage effluents

    • Author(s)
      P.Chou et al.
    • Journal Title

      Wat.Sci.Tech. (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] NAPL affects on benzo[a]pyrene biodegradation in soil by the indigenous microbiota and through bioaugmentation,

    • Author(s)
      R.Kanaly et al.
    • Journal Title

      Wat.Sci.Tech. (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] Indirubin, the red shade of indigo, chaptor 18 : Arylhydrocarbon receptor ligand activity of indirubin2006

    • Author(s)
      T.Matsuda, J.Adachi
    • Total Pages
      300
    • Publisher
      Life in Progress Editions, Roscoff. France
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] "Indirubin, the red shade of indigo", chapter 18:Arylhydrocarbon receptor ligand acitivity of indirubin2006

    • Author(s)
      T.Matsuda, J.Adachi
    • Publisher
      Life in Progress Editions, Roscoff, France(in press)
    • Related Report
      2005 Annual Research Report
  • [Book] 「京大人気講義シリーズ 地球環境学のすすめ」第6章2004

    • Author(s)
      松田知成(分担執筆)
    • Total Pages
      257
    • Publisher
      丸善株式
    • Related Report
      2004 Annual Research Report

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

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