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Synthetic Studies on Spider Toxins and Their Congeners and Their Biological Activities

Research Project

Project/Area Number 04557100
Research Category

Grant-in-Aid for Developmental Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionNagasaki University

Principal Investigator

IRIE Hiroshi  Faculty of Pharmaceutical Sciences, Nagasaki University Professor, 薬学部, 教授 (00025686)

Co-Investigator(Kenkyū-buntansha) TOKI Takashi  Research Center, Daicel Chemical Industries, LTD,Reseach Director, 研究所, 研究員
MIYASHITA Masaaki  Faculty of Science, Department of Chemistry, Professor, Hokkaido Univeresity, 理学部, 教授 (50006326)
HATAKEYAMA Susumi  Pharmaceutical Sciences, Nagasaki University Associate Professor, 薬学部, 助教授 (20143000)
Project Period (FY) 1992 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 1994: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 1993: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1992: ¥1,100,000 (Direct Cost: ¥1,100,000)
Keywordsspider toxin / polyamine / glutamic acid receptor / nervous toxin / nephilatoxins / histamine release / D-asparagine / ネフィラトキシン / 神経筋興奮伝達遮断 / ネフィラトキシン-8 / ネフィラトキシン類の全合成 / D-ネフィラトキシン-8 / D-ネフィラトキシン-12 / アジド中間体 / クモ毒素の全合成 / 神経筋興奮伝達遮断作用 / 含ポリアミンペプチド / アジド化合物
Research Abstract

Nephilatoxins have been isolated from the venom of Joro spider (Nephila clavata) , which show the potent blocking activity to glutamic acid receptor in brain and induce histamine release from rat peritoneal mast call. We aimed at the total synthesis of the toxins and their congeners to make ample supply of their toxins possible. The feature of toxins are characterized by the structure consisting of an aromatic acid, some amino acids, and polyamines. Therefore, the key point of their synthesis depends upon how to construct polyamine moiety included in the toxin structures. We developed a useful method for the purpose using azide group in the place of amino group.
Based on the basic precise reseach work, we accomplished total synthesis of six toxins NPTX-7,8,9,10,11, and 12 and D-NPTX-8 and 12 having D-aspargine in the place of L-amino acid originaly present in genuin toxins in large quantity. Biological test of the samples thus synthesized provided instructive information about structure-activity relationship.

Report

(4 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • 1992 Annual Research Report
  • Research Products

    (11 results)

All Other

All Publications (11 results)

  • [Publications] M. Miyashita et al.: "Synthetic studies on Spider Neurotoxins ( I) : Total Synthesis of Nephilatoxins ( NPTX-9 and NPTX-11 ), New Neurotoxins of Joro Spider ( Nephila clavata)" Tetrahedron Letters. 33. 2833-2836 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M. Miyashita et al.: "Synthetic studies on Spider Neurotoxins (II):Total Synthesis of Nephilatoxins ( NPTX-10 and NPTX-12) , New Neurotoxins of Joro Spider ( Nephila clavata)" Tetrahedron Letters. 33. 2837-2840 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M. Miyashita et al.: "Total Synthesis of Nephilatoxin-8( NPTX-8) , a New Neurotoxin of Joro Spider ( Nephila clavata)" Chemistry Letters. 929-932 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M. Miyashita et al.: "Total Synthesis of Nephilatoxin-7,a New Neurotoxins of Joro Spider ( Nephila clavata)" J. Chem. Soc. , Chem. Commun.1995( submitted). (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Miyashita, H.Sato, A.Yoshikoshi, T.Toki, M.Matsuhita, H.Irie, T.Yanami, Y.Kikuchi, C.Takasaki, and T.Nakajima: "synthetic Studies on Spider Neurotoxins (1) : Total Synthesis of Nephilatoxins (NPTX-9 and NPTX-11) , New Neurotoxins of Joro Spider (Nephila clavata)" Tetrahedron Letters. 33. 2833-2836 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Miyashita, H.Sato, M.Matsushita, Y.Kusumegi, T.Toki, A.Yoshikoshi, T.Yanami, Y.Kikuchi, C.Takasaki, T.Nakajima, and H.Irie: "Synthetic Studies on Spider Neurotoxins (II) : Total Synthesis of Nephilatoxins (NPTX-10 and NPTX-12) , New Neurotoxins of joro Spider (Nephila clavata)" Tetrahedron Letters. 33. 2837-2840 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Miyashita, M.Matsushita, H.Sato, t.Toki, T.Nakajima, and H.Irie: "Total Synthesis of Nephilatoxin-8 (NPTX-8) , a New Neurotoxin of Joro Spider (Nephila clavata)" Chemistry Letters. 929-932 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Miyashita, T.Kanemura, S.Hatakeyama, H.Irie, M.Miyashita, and T.Toki: "Total Synthesis of Nephilatoxin-7, a New Neurotoxin of Joro Spider (Nephila clavata)" J.Chem.Soc, Chem.Commun. (submitted).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masaaki Miyashita: "Total Synthesis of Nephilatoxin-8(NPTX-8),a New Neurotoxin of Joro Spider(Nephila clavata)" Chemistry Letters. 929-932 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Masaaki Miyashita: "Synthetic Studies on Spider Neurotoxins(I):Total Synthesis of Nephilatoxins(NPTX-9 and NPTX-11),New Neurotoxins of Joro Spider(Nephila clavata)" Tetrahedron Letters. 33. 2833-2836 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Masaaki Miyashita: "Synthetic Studies on Spider Neurotoxins(II):Total Synthesis of Nephilatoxins(NPTX-10 and NPTX-12),New Neurotoxins of Joro Spider(Nephila clavata)" 33. 2837-2840 (1992)

    • Related Report
      1992 Annual Research Report

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Published: 1992-04-01   Modified: 2016-04-21  

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