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Syntheses and Application of the Functional Compounds Designed to Study the Metabolism and the Mechanism of the Action of Vitamin D

Research Project

Project/Area Number 02670946
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

YAMADA Sachiko  Tokyo Med. and Dental Univ., Inst. Med. and Dental Eng., Professor, 医用器材研究所, 教授 (10014078)

Co-Investigator(Kenkyū-buntansha) SHIMIZU Masato  Tokyo Med. and Dental Univ., Inst. Med. and Dental Eng., Associate Professor, 医用器材研究所, 助教授 (50126231)
Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1991: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1990: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsVitamin D metabolites / Fluorescence-labeling / Fluorescent dienophile / Fluorometry / Chemical synthesis / Triazolinediones / Retinoic acid / Vitamin A
Research Abstract

1)To develop an accurate and precise method for assaying vitamin D metabolites in plasma, reagents to label vitamin D with fluorescence or chemoluminescence were designed and synthesized.
2)A highly fluorescent dienophile(named DMEQ-TAD), in which a fluorescent chromophore(dimethoxyquinoxalinone group)and a highly reactive dienophile(1, 2, 4-triazoline-3, 5-dione)were connected via a spacer, was successfully synthesized for the first time.
3)The reaction of the fluorescent dienophile(DMEQ-TAD)with major vitamin D_3 metabolites was examined and it was shown that all the metabolites were fluorescence-labeled in quantitative yields.
4)Fluorometry of plasma vitamin D metabolites was examined and new accurate fluorometric methods for assaying 25(OH)D_3 and 24, 25(OH)_2D_3 in plasma were developed.
5)A new and convenient stereoselective method for synthesizing 1, 25(OH)_2D_3 26, 23-lactone, a major metabolite of the active vitamin D_3, was developed.
6)Reaction of vitamin A derivatives with DMEQ-TAD was examined and it was shown that they react with the reagent with high regioselectivity indicating that the reagent might be useful for assaying the active vitamin A metabolite.

Report

(3 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] M.Shimizu,T.Takahashi,S.Uratsuka,and S.Yamada: "Synthesis of Highly FluorescentDienophiles for Detecting Conjugated Dienes in Biological Fluid" J.Chem.Soc.,Chem.Commun.1416-1417 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] M.Shimizu,S.Kamachi,Y.Nishii,and S.Yamada: "Synthesis of a Reagent for Fluorescence-Labeling of Vitamin D and Its Use in Assaying Vitamin D Metabolites" Analytical Biochem.194. 77-81 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] S.Yamada,K.Hamano,and M.Shimizu: "Reaction of Vitamin A with 1,2,4-Triazoline-3,5-diones" Tetrahedron Lett.32. 2379-2382 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] 山田 幸子,清水 正人: "ビタミンD代謝物の血中レベルの新しい測定法" The Bone. 5. 47-52 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] K.Yamamoto,M.Shimizu,S.Yamada,S.Iwata,O.Hoshino: "Facile Stereoselective Synthesis of (23S,25R)-1α,25-Dihydroxyvitamin D3 26,23-Lactone, a Major Metabolite of 1α,25-Dihydroxyvitamin D3" J.Org.Chem.57. 33-39 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] M.Shimizu,Y.Gao,T.Aso,K.Nakatsu,and S.Yamada: "Fluorometric Assay of 25-H^droxyvitamin D3 and 24R,25-Dihydroxyvitamin D3 in Plasma" Analytical Biochem.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] M. Shimizu, T. Takahashi, S. Uratsuka, and S. Yamada: "Synthesis of Highly Fluorescent Dienophiles for Detecting Conjugated Dienes in Biological Fluid" J. Chem. Soc., Chem. Commun.1416-1417 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] M. Shimizu, S. Kamachi, Y. Nishii, and S. Yamada: "Synthesis of a Reagent for Fluorescence-Labeling of Vitamin D and Its Use in Assaying Vitamin D Metabolites" Analytical Biochem.194. 77-81 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] S. Yamada, K. Hamano, and M. Shimizu: "Reaction of Vitamin A with 1, 2, 4-Triazoline-3, 5-diones" Tetrahedron Lett.32. 2379-2382 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] S. Yamada and M. Shimizu: "New Method for Assaying Plasma Vitamin D Metabolites" The Bone. 5. 47-52 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] K. Yamamoto, M. Shimizu, S. Yamada, S. Iwata, and O. Hoshino: "Facile Stereoselective Synthesis of (23S, 25R)-1alpha, 25-Dihydroxyvitamin D3 26, 23-Lactone, a Major Metabolite of 1alpha, 25-Dihydroxyvitamin D3" J. Org. Chem.57. 33-39 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] M. Shimizu, Y. Gao, T. Aso, K. Nakatsu, and S. Yamada: "Fluorometric Assay of 25-Hydroxyvitamin D3 and 24R, 25-Dihydroxyvitamin D3 in Plasma" Anal. Biochem.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Sachiko Yamada: "Development of the Method for Synthesizing the Lactone, the Major Metabolite of the Active Vitamin D_3 supposed to be Active in Bone Formation." Modern Medicine.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] S. Yamada, D. Morizono, and K. Yamamoto: "Mild Oxidation of Aldehydes to the Corresponding Carboxylic Acids and Esters : Alkaline Iodine Oxidation Revisited" Tetrahedron Lett.(1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] M.Shimizu,T.Takahashi,S.Uratsuka,and S.Yamada: "Synthesis of Highly FluorescentDienophiles for Detecting Conjugated Dienes in Biological Fluid" J.Chem.Soc.,Chem.Commun.1416-1417 (1990)

    • Related Report
      1991 Annual Research Report
  • [Publications] M.Shimizu,S.Kamachi,Y.Nishii,and S.Yamada: "Synthesis of a Reagent for FluorescenceーLabeling of Vitamin D and Its Use in Assaying Vitamin D Metabolites" Analytical Biochem.194. 77-81 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] S.Yamada,K.Hamano,and M.Shimizu: "Reaction of Vitamin A with 1,2,4ーTriazolineー3,5ーdiones" Tetrahedron Lett.32. 2379-2382 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 山田 幸子,清水 正人: "ビタミンD代謝物の血中レベルの新しい測定法" The Bone. 5. 47-52 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Yamamoto,M.Shimizu,S.Yamada,S.Iwata,O.Hoshino: "Facile Stereoselective Synthesis of(23S,25R)ー1α,25ーDihydroxyvitamin D3 26,23ーLactone,a Major Metabolite of 1α,25ーDihydroxyvitamin D3" J.Org.Chem.57. 33-39 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] M.Shimizu,Y.Gao,T.Aso,K.Nakatsu,and S.Yamada: "Fluorometric Assay of 25ーHydroxyvitamin D3 and 24R,25ーDihydroxyvitamin D3 in Plasma" Analytical Biochem.

    • Related Report
      1991 Annual Research Report
  • [Publications] M.Shimizu,T.Takahashi,S.Uratsuka,& S.Yamada: "Synthesis of Highly Fluorescent Dienophiles for Detecting Conjugated Dienes in Biological Fluid" J.Chem.Soc.,Chem.Commun.1416-1417 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] M.Shimizu,S.Kamachi,Y.Nishii,& S.Yamada: "Synthesis of a Reagent for FluorescenceーLabeling of Vitamin D and Its Use in Assaying Vitamin D Metabolites" Anal.Biochem.194. (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] M.Shimizu,K.Nakatsu,& S.Yamada: "Fluorimetric Assay of 25ーHydroxyvitamin D_3 in Plasma" Anal.Biochem.(1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] S.Yamada,K.Hamano,& M.Shimizu: "Reaction of Vitamin A with 1,2,4ーTriazolineー3,5ーdiones" Tetrahedron Lett.

    • Related Report
      1990 Annual Research Report
  • [Publications] K.Yamamoto,M.Shimizu,S.Yamada,S.Iwata,& O.Hoshimno: "Facile Stereoselective Synthesis of(23S,25R)ー1,25ーDihydroxyーvitamin D_3 26,23ーLactone,a Major Matabolite of 1,25ーDihydroxyーvitamin D_3" J.Org.Chem.

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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