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A Study on Designed Hapten Aimed at Anti-ciguatoxin Monoclonal Antibody

Research Project

Project/Area Number 10558096
Research Category

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

Allocation TypeSingle-year Grants
Section展開研究
Research Field Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

HIRAMA Masahiro  Tohoku University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (30165203)

Co-Investigator(Kenkyū-buntansha) OGURI Hiroki  Tohoku University, Graduate School of Science, Assistant Professor, 大学院・理学研究科, 助手 (80311546)
TOMIOKA Yoshihisa  Tohoku University, Tohoku University Hospital, Assistant Professor, 医学部・附属病院, 助手 (00282062)
MIZUGAKI Michinao  Tohoku University, Tohoku University Hospital, Professor, 医学部・附属病院, 教授 (60004595)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥12,500,000 (Direct Cost: ¥12,500,000)
Fiscal Year 2000: ¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 1999: ¥4,300,000 (Direct Cost: ¥4,300,000)
Fiscal Year 1998: ¥5,000,000 (Direct Cost: ¥5,000,000)
Keywordsciguatoxin / antibody / hapten / antigen / gene / synthesis / olefin metathesis / ELISA / モノクローナル抗体 / 人工抗原 / シガテラ / 抗シガトキシン抗体 / 海産ポリエーテル / コンジュゲート / 免疫
Research Abstract

The ABC-ring fragment of ciguatoxin was synthesized as a C2 epimeric mixture (1 : 1 ). The mixture, which was designed as a possible hapten for preparing an anti-ciguatoxin monoclonal antibody, was conjugated with a carrier protein (KLH) and then used for immunization of mice. The three monoclonal antibodies (mAbs) obtained have shown an appreciable reactivity to the hapten. Each mAb discriminated configuration of the C2 hydroxy group of the ABC-ring fragment. The mAb which showed reactivity to the 2S-fragment was cross-reacted with ciguatoxin. Furthermore, new and efficient synthetic methods utilizing olefin methathesis were developed and several designed haptens have been prepared and conjugated with KLH and BSA, which have been used for immunization of mice.

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (35 results)

All Other

All Publications (35 results)

  • [Publications] T.Oishi,Y.Nagumo,and M.Hirama,: "Convergent Synthesis of the trans-Fused 6-n-6-6 (n=7-10) Tetracycric Ether System Based on a Ring-closing Metathesis Reaction."Chem.Commun.. 1041-1042 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Oguri,S.Sasaki,S.Hishiyama,T.Oishi,M.Hirama,T.Tumuraya,Y.Tomioka,and M.Mizugaki,: "Designed Hapten Aimed at Anti-ciguatoxin Monocronal Antibody : Synthesis, Immunization and Descrimination of the C2 Configuration."Synthesis, Special Issue,. 1431-1436 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Oishi,M.Maruyama,M.Shoji,K.Maeda,N.Kumahara,S.Tanaka,and M.Hirama,: "Enantioselective Synthesis of the Medium Ring Ethers, Tetrahydrooxepin, Oxocane and Hexahydrooxonin, of Ciguatoxin. Extensive Ring-Expansion and Chemoenzymatic Desymmetrization Strategy."Tetrahedron,. 55. 7471-7498 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Maeda,T.Oishi,H.Oguri,and M.Hirama,: "Convergent Synthesis of the ABCDE Ring Framework of Ciguatoxin."Chem.Commun.,. 1063-1064 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Oguri,S.Sasaki,T.Oishi,and M.Hirama,: "Expeditious Tandem-Metathesis Route to the AB-ring Fragment of Ciguatoxin."Tetrahedron Lett.,. 40. 5405-5408 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Oishi,Y.Nagumo,M.Shoji,J.-Y.Le Brazidec,H.Uehara,and M.Hirama,: "Convergent Synthesis of the IJKLM Ring Fragment of Ciguatoxin CTX3C."Chem.Commun.. 2035-2036 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 大石徹,平間正博: "最新のトピックス「閉環メタセシス反応の新たなる展開-不斉触媒化」"化学. 54. 66 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Oguri,S.Tanaka,T.Oishi,and M.Hirama,: "A Very Short Route to the Functionalized A-ring Moiety of Ciguatoxin."Tetrahedron Lett.,. 41. 975-978 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Maruyama,K.Maeda,T.Oishi,H.Oguri,and M.Hirama,: "Convergent Strategy for Synthesizing Polycyclic Ether Marine Toxins : Synthesis of the ABCDE Ring Fragment of Ciguatoxin CTX3C."Heterocycles,. 54. 93-99 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Oishi,H.Uehara,Y.Nagumo,M.Shoji,J-Y.Le Brazidec,M.Kosaka,and M.Hirama,: "Practical Entry into the HIJKLM Ring Segment of Ciguatoxin CTX3C."Chem.Commun.,. 381-382 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Oishi,S.Tanaka,Y.Ogasawara,K.Maeda,H.Oguri,and M.Hirama,: "Highly Stereocontrolled Synthesis of the ABCD Ring Fragment of Ciguatoxin CTX3C."Synlett,. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Nagumo,H.Oguri,Y.Shindo,S.Sasaki,T.Oishi,M.Hirama,Y.Tomioka,M.Mizugaki,and T.Tsumuraya,: "A Surface Plasmon Resonance Study of the Monoclonal Antibodies Bindng to the Synthetic ABC-ring Fragments of Ciguatoxins"(submitted for publication).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Oishi, Y.Nagumo, and M.Hirama: "Convergent Synthesis of the trans-Fused 6-n-6-6- (n=7-10) Tetracycric Ether System Based on a Ring-closing Metathesis Reaction"Chem.Commun.. 1041-1042 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Oguri, S.Sasaki, S.Hishiyama, T.Oishi, M.Hirama, T.Tumuraya, Y.Tomioka and M.Mizugaki: "Designed Hapten Aimed at Anti-ciguatoxin Monocronal Antibody : Synthesis, Immunization and Descrimination of the C2 Configuration."Synthesis, Special Issue. 1431-1436 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Oishi, M.Maruyama, M.Shoji, K.Maeda, N.Kumahara, S.Tanaka, and M.Hirama: "Enantioselective Synthesis of the Medium Ring Ethers, Tetrahydrooxepin, Oxocane and Hexahydrooxonin of Ciguatoxin Extensive Ring-Expansion and Chemoenzymatic Desymmetrization Strategy."Tetrahedron. 55. 7471-7498 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Maeda, T.Oishi, H.Oguri, and M.Hirama: "Convergent Synthesis of the ABCDE Ring Framework of Ciguatoxin."Chem.Commun.. 1063-1064 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Oguri, S.Sasaki, T.Oishi, and M.Hirama: "Expeditious Tandem-Metathesis Route to the AB-ring Fragment of Ciguatoxin."Tetrahedron Lett.. 40. 5405-5408 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Oishi, Y.Nagumo, M.Shoji, J.-Y.Le Brazidec, H.Uehara, and M.Hirama: "Convergent Synthesis of the IJKLM Ring Fragment of Ciguatoxin CTX3C."Chem.Commun.. 2035-2036 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Oguri, S.Tanaka, T.Oishi, and M.Hirama: "A Very Short Route to the Functionalized A-ring Moiety of Ciguatoxin."Tetrahedron Lett.. 41. 975-978 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Maruyama, K.Maeda, T.Oishi, H.Oguri, and M.Hirama: "Convergent Strategy for Synthesizing Polycyclic Ether Marine Toxins : Synthesis of the ABCDE Ring Fragment of Ciguatoxin CTX3C."Heterocycles. 54. 93-99 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Oishi, H.Uehara, Y.Nagumo, M.Shoji, J-Y.Le Brazidec, M.Kosaka, and M.Hirama: "Practical Entry into the HIJKLM Ring Segment of Ciguatoxin CTX3C."Chem.Commun.. 381-382 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Oishi, S.Tanaka, Y.Ogasawara, K.Maeda, H.Oguri, and M.Hirama: "Highly Stereocontrolled Synthesis of the ABCD Ring Fragment of Ciguatoxin CTX3C."Synlett. (in press.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Naguo, H.Oguri, Y.Shindo, S.Sasaki, T.Oishi, M.Hirama. Y.Tomioka, M.Mizugaki, and T.Tsumuraya: "A Surface Plasmon Resonance Study of the Monoclonal Antibodies Bindng to the Synthetic ABC-ring Fragments of Ciguatoxins."(submitted for publication.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Oguri: "A Very Short Route to the Functionalized A-ring Moiety of Ciguatoxin."Tetrahedron Lett.. 41. 975-978 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] M.Maruyama: "Convergent Strategy for Synthesizing Polycyclic Ether Marine Toxinsi Synthesis of the ABCDE Ring Fragment of Ciguatoxin CTX3C."Heterocycles. 54. 93-99 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Oishi: "Practical Entry into the HIJKLM Ring Segment of Ciguatoxin CTX3C."Chem.Commun.. 381-382 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Oishi: "Highly Stereocontrolled Synthesis of the ABCDE Ring Fragment of Ciguatoxin CTX3C."Synlett,. (in press).

    • Related Report
      2000 Annual Research Report
  • [Publications] Hiroki Oguri: "Designed Hapten Aimed at Anti-ciguatoxin Monocronal Antibody: Synthesis, Immunization and Descrimination of the Ce Configuration"Synthesis. Spcial Issue. 1431-1436 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Oishi: "Enantioselective Synthesis of the Medium Ring Ethers, Tetrahydrooxepin, Oxocare and Hexahydrooxnin, of Ciguatoxin. Extensive Ring-Expansion and chemoenzymatic Desymmetrization Strategy"Tetrahedron. 55. 7471-7498 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Maeda: "Convergent Synthesis of the ABCDE Ring Framework of Ciguatoxin"Chem. Commun.. 1063-1064 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Oguri: "Expeditions Tandem-Metathesis Route to the AB-ring Fragment of Ciguatoxin"Tetrahedron Lett.. 40. 5405-5408 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Oishi: "Convergent Synthesis of the IJKLM Ring Fragment of Ciguatoxin CTX3C"Chem. Commun.. 2035-2036 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Oguri: "A Very Short Route to the Functionalized A-ring Moiety of Ciguatoxin"Tetrahedron Lett.. 41. 975-978 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hiroki Oguri et al.: "Designed Hapten Aimed at Anti-ciguatoxin Antibody:Synthesis,Immunization and Discrimination of the C2 Configuration" SYNTHESIS. (発表予定). (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Tohru Oishi et al.: "Convergent synthesis of the trans-fused 6-n-6-6(n=7-10)tetracyclic ether system based on a ring-closing metathesis reaction" Chem.Commun.1041-1042 (1998)

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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