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Studies on Novel Syntheses of Fluorecent Tripodal Hexadentate Iigands and Than Application to fluorescent Probes for Microscopic Observation of Cells

Research Project

Project/Area Number 15550152
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemistry related to living body
Research InstitutionSeikei University

Principal Investigator

KATOH Akira  Seikei University, Faculty of Engineering, Professor, 工学部, 教授 (00167339)

Co-Investigator(Kenkyū-buntansha) SAITO Ryota  Seikei University, Faculty of Engineering, Research Associate, 工学部, 助手 (90327974)
Project Period (FY) 2003 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2004: ¥2,400,000 (Direct Cost: ¥2,400,000)
Fiscal Year 2003: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsFluorescent bidentate ligand / Ouinoxaline / PH sensing / Static quenching / Fluorescent probe / Fluorescence derivatization reagent / Imidazopyrazine / Superoxide radical anion / 3-ヒドロキシ-4(1H)-ピリジノン / カテコール / 鉄錯体 / 蛍光プロープ / 3-ヒドロキシピリドン / 蛍光のON-OFF
Research Abstract

In this project, we investigated syntheses of novel fluorescent bidentate and hexadentate ligands and their application to the fluorescent probes for microscopic observation of cells. The following points became dear.
1.Anew fluorescent bidentate ligand (a), 3-hydroxy-4(1H)-pyridinone directly attached to quinoxaline, was synthesized. 2.Anew fluorescent bidentate ligand (b), 6-(2',3'-dihydroxybenzyl)amino-2,3-dimorpholino quinoxaline, was synthesized. 3.A chiral quinoxaline (c) bearing the L-praline residue at C-6 position was synthesized. 4.A fluorescent imidazopyrazine (d) bearing diaryl substituents at C-6 and C-8 positions was synthesized 5.Unfortunately, the desired fluorescent tripodal hexadentate ligands could not be obtained owing to the insolubility of synthetic intermediates. 6.The bidentate ligand (a) formed 3:1 complexes with Fe(III), Al(III), Ga(III), and Cr(III). The fluorescence was efficiently quenched by the metal complex formation via the Perrin model of static quenchi … More ng, the quenching efficiency being in order of Fe(III)>>Al(III)>Ga(M)>Cr(III). The fluorescence was recoverd by removal of Fe(III) with N-benzoyl desfenioxamine B. 7.In case of bidentate ligand (b), a unique absorption band due to the intramolecular charge transfer from the catechol moiety to electro-defident quinoxaline was observed under basic conditions. 8.The derivatization of mcemic naproxen, ibuprofen, and 2 phenylpropionic acid with chiral quinoxaline (c) afforded the diastereomers, which were dearly separated within 16 min on reversed phase HPLC with a detection limit of 5 pmol/10 μL injection volume at S/N=5. 9.Imidazopyrazine (d) showed enough sensitivity to superoxide in comparison with luminol and appears to be capable of superoxide detection. Further, imidazopytazine (d) exhibited the pH dependent bimodal chemiluminescence. These properties of imidazopyrazine(d) allows us to apply it for simultaneous detection of the two concurrent events, superoxide evaluation and pH titration, in biological systems. Less

Report

(3 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • Research Products

    (20 results)

All 2005 2004 Other

All Journal Article (18 results) Publications (2 results)

  • [Journal Article] High-Performance Liquid Chromatographic Enantio-Separation Based on Diastereomer Formation with New fluorescent Chiral Quinoxalines2005

    • Author(s)
      加藤 明良
    • Journal Title

      Heterocycles 65

      Pages: 1111-1120

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] High-Performance Liquid Chromatographic Enantio-Separation Based on Diastereomer Formation with New Fluorescent Chiral Quinoxaline2005

    • Author(s)
      Akira Katoh, Ryoji Yamamoto, Takeshi Fujimoto, Ryota Saito
    • Journal Title

      Heterocycles 65-5

      Pages: 1111-1120

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] アジン系複素環化合物の合成とそれらの機能性分子への変換2004

    • Author(s)
      加藤 明良
    • Journal Title

      有機合成化学協会誌 62

      Pages: 335-346

    • NAID

      10012854842

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Well Divided and pH-dependent Bimodal Chemiluminescence of 2-Methyl-6-phenyl-8-(4-substituted phenyl)imidazo[1,2-a]pyrazin-3(7H)-ones Induced by O_22004

    • Author(s)
      齋藤 良太
    • Journal Title

      Heterocycles 63

      Pages: 759-764

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 6-(2',3'-ジヒドロベンジル)アミノ-2,3-ジモルホリノキノキサリンの合成とその金属錯体の蛍光特性2004

    • Author(s)
      加藤 明良
    • Journal Title

      日本化学会第84春季年会講演予稿集II

      Pages: 1322-1322

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Studies on the Chemiluminescence Mechanism of Cypridina Luciferin Analogues : Dissociation Constants of Singlet-Excited Cypridina Oxyluciferin Analogues2004

    • Author(s)
      齋藤 良太
    • Journal Title

      Abstracts of the 13^<th> International Symposium on Bioluminescence and Chemiluminescence

      Pages: 148-148

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 6,8-Diarylimidazo[1,2-a]pyrazin-3(7H)-ones as Potential Chemiluminescent pH/Su peroxide Double Sensors2004

    • Author(s)
      齋藤 良太
    • Journal Title

      Abstracts of the 13^<th> International Symposium on Bioluminescence and Chemiluminescence

      Pages: 172-172

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Aime type Heterocyclic Compounds and Their Conversion into Functional Molecules2004

    • Author(s)
      Akira Katoh, Ryota Saito
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan 62-4

      Pages: 335-346

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Well Divided and pH-Dependent Bimodal Chemiluminescence of 2-Methyl-6-phenyl-8-(4-substituted phenyl)imidazo[1,2-a]pyrazin-3(7H)-ones Induced by Superoxide Anion2004

    • Author(s)
      Ryota Saito, Chizuru Inoue, Akira Katoh
    • Journal Title

      Heterocycles 63-4

      Pages: 759-764

    • NAID

      40006266612

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of 6-(2', 3'-dihydroxybenzyl)amino-2, 3-dimorpholinoquinoxaline And Fluorescent Characteristic of Its Metal Complex2004

    • Author(s)
      Akira Katoh, Keita Matsui, Ryota Saito
    • Journal Title

      Abstracts 11 for 84^<th> Spring Meeting of the Chemical Society of Japan

      Pages: 1322-1322

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Studies on the Chemiluminescence Mechanism of Cypridina Luciferin Analogues: Dissociation Constants of Singlet-Excited Cypridina Oxyluciferin Analogues2004

    • Author(s)
      Ryota Saito, Eriko Iwasa, Akira Katoh
    • Journal Title

      Abstracts of the 13^<th> International Symposium on Bioluminescence and Chemiluminescence

      Pages: 148-148

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 6, 8-Diarylimidazo[1, 2-a]pyrazin-3(7H)-ones as Potential Chemiluminescent pH/Superoxide Double Sensors2004

    • Author(s)
      Ryota Saito, Naoko suga, Akira Katoh, Shoji Maki, Takashi Hirano, Haruki Niwa
    • Journal Title

      Abstracts of the 13^<th> International Symposium on Bioluminescence and Chemiluminescence

      Pages: 172-172

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Well-Divided and pH-Dependent Bimodal Chemiluminescence of 6-phenyl-8-(4-substd, phenyl)imidazo[1.2-a]pyrazin-3(7H)-ones Induced by Superoxide Anion2004

    • Author(s)
      齋藤 良太
    • Journal Title

      Heterocycles 63・4

      Pages: 759-764

    • Related Report
      2004 Annual Research Report
  • [Journal Article] アジン系複素環化合物の合成とそれらの機能性分子への変換2004

    • Author(s)
      加藤 明良
    • Journal Title

      有機合成化学協会誌 62・4

      Pages: 335-346

    • NAID

      10012854842

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Studies on the Chemiluminescence Mechanism of Cypridina Luciferin Analogues : Dissociation Constants of Sigalet-Excited Cypridina Oxyluciferin Analogues2004

    • Author(s)
      齋藤 良太
    • Journal Title

      Luminescence, J.Biol.& Chem.Luminescence 19・3

      Pages: 148-148

    • Related Report
      2004 Annual Research Report
  • [Journal Article] 6,8-Diarylimidazo[1,2-1]pyrazin-3(7H)-ones as Potential Chemiluminescent pH/Superoxide Double Sensors2004

    • Author(s)
      齋藤 良太
    • Journal Title

      Luminescence, J.Biol.& Chem.Luminescence 19・3

      Pages: 172-172

    • Related Report
      2004 Annual Research Report
  • [Journal Article] High-Performance Liquid Chromatographic Enantio-Separation Based on Diastereomer Formation with New Fluorescent Chiral Quinoxalines2004

    • Author(s)
      加藤 明良
    • Journal Title

      Heterocycles 65・5(印刷中)

    • Related Report
      2004 Annual Research Report
  • [Journal Article] 2-アセチルアミノ-5-アリールピラジン類の蛍光特性2004

    • Author(s)
      齋藤 良太
    • Journal Title

      第34回複素環化学討論会講演要旨集 20-05

      Pages: 183-184

    • Related Report
      2004 Annual Research Report
  • [Publications] 加藤明良: "アジン系複素環化合物の合成とそれらの機能性分子への変換"有機合成化学協会誌. 62・4(印刷中). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] 加藤明良: "6-(2',3'-ジヒドロキシベンジル)アミノ-2,3-ジモルホリノキノキサリンの合成とその金属錯体の蛍光特性"日本化学会第84春季年会講演予稿集II. 2PB-085. 1322 (2004)

    • Related Report
      2003 Annual Research Report

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Published: 2003-04-01   Modified: 2016-04-21  

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