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Relationship between the 9-substituents of 11Z-retinal analogs and the visual function

Research Project

Project/Area Number 09672292
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 InstitutionKobe Pharmaceutical University

Principal Investigator

ITO Masayoshi  Kobe Pharm. Univ., Professor, 薬学部, 教授 (20068331)

Co-Investigator(Kenkyū-buntansha) WADA Akimori  Kobe Pharm. Univ., Associate Professor, 薬学部, 助教授 (80158683)
Project Period (FY) 1997 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1999: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1998: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1997: ¥1,000,000 (Direct Cost: ¥1,000,000)
KeywordsTricarbonyliron complex / 11Z-Retinal analog / 9-Substituted 11Z-retinal / Vision / Rhodopsin / Activation of signal transduction / 11Z-9位置換レチナール / β-イオノンアナログ鉄カルボニル錯体 / β-イオノンアナログ / 11Z-レチナ-ルアナログ / 9-ベンジルレチナ-ル / 9-フェニルレチナ-ル
Research Abstract

Rhodopsin is the visual pigment which contains 11Z-retinal as a chromophore bound to the ε-amino group of the apoprotein lysine residue through a protonated Schiff base. Recently, it was suggested that an interaction between the 9-methyl group of retinal and the amino acid residues of apoprotein played an important role for exhibiting the biological function. In order to clarify the effect of 9-substituents in rhodopsin chromophore, we prepared the various retinal analogs, which have the different substituents at 9 position in retinal (Et, iso-Pr, iso-Bu, t-Bu, Ph, CHィイD22ィエD2Ph, CHィイD22ィエD2CィイD26ィエD2HィイD24ィエD2-OMe-p, 1-naphthylmethyl, 2-naphthylmethy and 3-indolylmethyl), according to our developed method using tricarbonyliron complex and their interaction with bovine opsin was investigated. The retinal analogs except for t-Bu, Ph and 1-naphthylmethyl bounded to apoprotein and the artificial rhodopsin analogs were produced. And also, it was found that the iso-Pr and benzly analogs exhibited about 70-80% activation of signal transduction compared to that of native rhodopsin.

Report

(4 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • 1997 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] A. Wada: "Stereoselective Synthesis of 9-Demethyl-9-benzyl and 9-phenlyl-retinals and Their Interaction with Bovine Opsin"Bioorg. Med. Chem. Lett.,. 8(5). 423-426 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A. Wada: "Retinoids and Related Compounds. Part22. Synthesis of β-Ionone Analog Tricarbonyliron Complexes"Chem. Pharm. Bull.,. 47(2). 171-176 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A. Wada: "レチノイド異性体の立体選択的合成とタンパク質機能解明への応用"ビタミン. 74(3). 101-112 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A. Wada: "A Highly Stereoselective Synthesis of 11Z-Retinal Using Tricarbonyliron Complex"J. Org. Chem.. 65(in press). (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A. Wada, N. Fujioka, H. Imai, Y. Shichida, M. Ito: "Stereoselective Synthesis of 11Z-9-Demethyl-9-benzyl- and 9-phenyl-retinals and their Interaction with Bovine Opsin"Bioorg. Med. Chem. Lett.. 8(5). 423-426 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A. Wada, N. Fujioka, M. Ito: "Retinoids and Related Compounds. Part 22. Synthesis of β-Ionone Analog-tricabonyliron Complexes"Chem. Pharm. Bull.. 47(2). 171-176 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A. Wada: "Stereoselective Synthesis of Retinoid Isomers and Its Application to the Investigation of Protein Functions"Vitamin. 74(3). 101-112 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A. Wada, N. Fujioka, Y. Tanaka, M. Ito: "A Highly Steroselective Synthesis of 11Z-Retinal Using Tricarbonyliron Complex"J. Org. Chem.. 65, (in press). (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A.Wada: "レチノイド異性体の立体選択的合成とタンパク質機能解明への応用"ビタミン. 74(3). 101-112 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] A.Wada: "A Highly Stereoselective Synthesis of 11Z-Retinal Using Tricarbonyliron Complex"J.Org.Chem.. 65(in press). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] A.Wada: "Stereoselective Synthesis of 11Z-9-Demethyl-9-benzyl and 9-phenyl-retinals and Their Interaction with Bovine Opsin" Bioorg.Med.Chem.Lett.,. 8(5). 423-426 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] A.Wada: "Retinoids and Related Compounds.Part 22.Synsthesis of β-Ionone Analog Tricarbonyliron Complex" Chem.Pharm.Bull.,. 47(2). 171-176 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] A.Wada: "Stereoselective Synthesis of 11Z-9-Demethyl-9-benzyl and 9-phenyl-retinals and Their Interaction with Bovine Opsin" Bioorg.Med.Chem.Lett.,. (in press). (1998)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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