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Design and Synthesis of New Sensitive Dienophiles, and Application to the Quantitative Analysis of Biologically Active Conjugated Dienes

Research Project

Project/Area Number 05671741
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionTokyo Medical and Dental University

Principal Investigator

SHIMIZU Masato  Tokyo Medical and Dental University, Institute for Medical and Dental Engineering, Associate Professor, 医用器材研究所, 助教授 (50126231)

Co-Investigator(Kenkyū-buntansha) YAMAMOTO Keiko  Tokyo Medical and Dental University, Institute for Medical and Dental Engineerin, 医用器材研究所, 助手 (90147017)
YAMADA Sachiko  Tokyo Medical and Dental University, Institute for Medical and Dental Engineerin, 医用器材研究所, 教授 (10014078)
Project Period (FY) 1993 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1994: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1993: ¥1,000,000 (Direct Cost: ¥1,000,000)
Keywordsfluorescent dienophile / fluorometric assay / conjugated dienes / cycloaddition reaction / vitamin D metabolites / retinoic asid / microcystin / chemiluminescence / 蛍光ラベル化 / 付加反応
Research Abstract

1. Synthesis of highly sensitive dienophiles
Fluorescent or chemiluminescent dienophiles targeting conjugated diene were designed and synthesized. A highly sensitive chemiluminescent dienophile, in which a chemiluminescent chromophore (acridinium ester group) and a reactive 1,2,4-triazoline-3,5-dione group were connected, was newly synthesized.
2.A fluorescent dienophile (DMEQ-TAD) was applied to the fluorometric analysis of vitamin D,vitamin A and microcystins.
(1) Fluorometric analysis of plasma vitamin D metabolites was examined and new accurate methods for assaying 25-OHD_3,24,25-(OH)_2D_3 and an active hormone 1,25-(OH)_2D_3 in human plasma were successfully developed.
(2) Reactions of DMEQ-TED with retinoic acid and its geometrical isomers having a pentaene system were examined. Except for the 9Z-isomer, reactions gave the mono-adducts in high selectivity while the 9Z-isomer gave only the bis-adducts indicating that DMEQ-TAD might be useful as a fluorescence labeling for retinoic acids in biological fluid.
(3) DMEQ-TAD reacted with microcystins, a cyclic heptaptide toxin from blue-green algae, at the conjugated diene part to yield the cycloadducts. The fluorometric method for assaying enviromental microcystins is under investigation.

Report

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

    (29 results)

All Other

All Publications (29 results)

  • [Publications] M.Shimizu: "Fluorescence-Labeling Reaction of Vitamin D Metabolites and Analogs with Fluorescent 1,2,4-triazoline-3,5-dione (DMEQ-TAD)" BioMed.Chem.Lett.9. 1809-1814 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] K.Yamamoto: "Stereoselective Syntheses of(22R)-and(22S)-22-Methyl-1α,25-dihydroxyvitamin D3:Active Vitamin D3 Analogs with Restricted Side Chain Conformation" J.Org.Chem.58. 2530-2537 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] G.Ying: "The Effects of Chemotherapy Including Cisplation on Vitamin D Metabolism" Endocrine J.40. 737-742 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] 山本恵子: "活性型ビタミンDの側鎖の立体配座を固定したアナログの設計,合成及び生理活性" 医用器材研究所報告. 27. 21-32 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Shimizu: "Reaction of Geometrical Isowers of Retinoic Acid with 1,2,4-Triazoline-3.5-dione Having Fluorescent Chromophore" Tetrahedron Lett.35. 1917-1920 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] 清水正人: "共役ジエンを標的とする新蛍光標識試薬の開発ならびに同試薬のビタミンDおよびA代謝物定量への応用" ビタミン. 68. 15-30 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] 山田幸子: "ビタミンDと亜硫酸ガス(SO_2)との反応および同反応のビタミンDの化学修飾への応用" ビタミン. 68. 135-144 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y.Imae: "Biological Activities of 24-Fluoro-1α,25-dihydroxyvitamin D-2 and Its 24-Epimer" Biochim.Biophys.Acta. 1213. 302-308 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] 清水正人: "新しい蛍光標識求ジエン試薬:合成ならびにビタミンD,Aおよびマイクロシスチンとの反応と高感度定量分析への応用" 医用器材研究所報告. 28. 11-27 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Shimizu, T.Yamasaki, S.Yamada: "Fluorescence-Labeling Reaction of Vitamin D Meta-bolites and Analogs with Fluorescent 1,2,4-Triazoline-3,5-dione (DMEQ-TAD)" BioMed.Chem.Lett.9. 1809-1814 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] K.Yamanoto, J.Takahashi, K.Hamano, S.Yamada, K.Yamaguchi, H.Deluca: "Stereoselective Syntheses of (22R) -and (22S) -22-Methy1-1alpha, 25-dihydroxyvitamin D_3 : Active Vitamin D_3 Analogs with Rectricted Side Chain Conformation" J.Org.Chem. 58. 2530-2537 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] G.Ying, M.Shimizu, S.Yamada, Y.Ozaki, T.Aso: "The Effects of Chemotherapy Including Cisplatin on Vitamin D Metabolism" Endocrine J.40. 737-742 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] K.Yamamoto, S.Yamada: "Design, Synthesis and Biological Activities of Active Vitamin D_3 Analogs with a Restricted Side Chain Conformation" Iyo Kizai Kenkyusho Hokoku. 27. 21-32 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Shimizu, K.Yaguchi, Y.Iwasaki, S.Yamada: "Reaction of Geometrical Isomers of Retinoic Acid with 1,2,4-Triazoline-3,5-dione Having Fluorescent Chromophore" Tetrahedron Lett.35. 1917-1920 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Shimizu, S.Yamada: "New Fluorescence-Labeling Reagent Targeting Conjugated Dienes : Application to the Fluorometric Analysis of Vitamin D and A Metabolites" Vitamin. 68. 15-30 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] S.Yamada, H.Takayama: "Reaction of Vitamin D with Sulfur Dioxide, and Its Application to the Structural Modiffication of Vitamin D." Vitamin. 68. 135-144 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y.Imae, A.Manaka, N.Yoshida, Y.Ishimi, T.Shinki, E.Abe, T.Suda, H.Takayama, S.Yamada: "Biological activities of 24-fluoro-1alpha, 25-dihydrovitamin D-2 and it 24-epimer" Biochim.Biophys.Acta. 1213. 302-308 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Shimizu, Y.Iwasaki, S.Yamada: "New Fluorescence-Labeling Dienophile : Synthesis, Reaction with Vitamin D,A,and Microcystins, and Apllication to Their Highly Sensitive Assaya" Iyo Kizai Kenkyusho Hokoku. 28. 11-27 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Shimizu: "Reaction of Geometrical Isomers of Retinoic Acid with 1,2,4-Triazoline-3,5-dione Having Fluorescent Chromophore" Tetrahedron Lett.35. 1917-1920 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 山田幸子: "ビタミンDと亜硫酸ガス(SO_2)との反応および同反応のビタミンDの化学修飾への応用" ビタミン. 68. 135-144 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Y.Imae: "Biological Activities of 24-Fluoro-1α,25-dihydroxyvitamin D-2 and Its 24-Epimer" Biochem. Biophys. Acta. 1213. 302-308 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 清水正人: "新しい蛍光標識求ジエン試薬:合成ならびにビタミンD,Aおよびマイクロシスチンとの反応と高感度定量分析への応用" 医用器材研究所報告. 28. 11-27 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 清水正人: "メタクリル酸メチル(MMA)の犬静脈内投与によるビタミンD代謝への影響" 医用器材研究所報告. 28. 46-50 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 山本恵子: "活性型ビタミンDの側鎖の立体配座を固定したアナログ設計,合成及び生理活性" 医用器材研究所報告. 27. 21-32 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Yamamoto: "Stereoselective syntheses of(22R)-and(22S)-22-methyl-1α,25-dihydroxyvitamin D_3:Active viatamin D_3 analogs with restricted side chain conformation" J.Org.Chem.58. 2530-2537 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] M.Shimizu: "Fluorescence-labeling reaction of vitamin D metabolites and analogs with fluorescent 1,2,4-triazoline-3,5-dione(DMEQ-TAD)" BioMed.Chem.Lett.9. 1809-1814 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Y.Gao: "The effects of chemotherapy including cisplatin on vitamin D metabolism" Endocrine J.40. 737-742 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] 清水 正人: "共役ジエンを標的とする新しい蛍光標識試薬の開発並びにそのビタミンDおよびビタミンA代謝物の定量への応用" ビタミン. 68. 15-30 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] M.Shimizu: "Reaction of geometrical isomers of retinoic acid with 1,2,4-triazoline-3,5-dione having fluorescent chromophore" Tetrahedron Lett.(in press). (1994)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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