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Development and application of novel caged compounds for clucidation of immune responce

Research Project

Project/Area Number 08680639
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionToho University

Principal Investigator

IWAMURA Michiko  Toho University, Faculty of Science, Professor, 理学部, 教授 (90057597)

Co-Investigator(Kenkyū-buntansha) KOBAYASHI Yoshiro  Toho University, Faculty of Science, Professor, 理学部, 教授 (10134610)
Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1997: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1996: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsCaged compounds / Apoptosis / Immune responce / Cytotoxic activity / Sugar-modified 2-nitrobenzyil / Cell recognition / Macrophage / ケージド化合物 / ロイシルロイシンメチルエステル / 糖を修飾したニトロベンジル基 / マクロファージ系細胞株 / 5-O-(β-Glucopyranosyl)-2-Nitrobenzyl
Research Abstract

Leucyl-leucine methyl ester, known as an apoptosis inducer to macrophages and NK cells, was caged with glucose modified 2-nitrobenzyl to increase solubility in PBS containing 1%DMSO.5-0-(beta-glucopyranosyl)-2-nitrobenzyl caged Leu- Leu-OMe 2a, soluble as high as 0.5 mM,was synthesized through 9 steps using glucose and 5-hydroxy-2-nitro benzaldehyde as starting materials. Upon irradiation at 350nm, it released Leu-Leu-OMe and induced apoptosis to HL60 cells more effectively than 2-nitrobenzyl caged Leu-Leu-OMe. 5-0- (beta-glucopyranosyl) -2-nitrophenethyl caged Leu-Leu-OMe 3 was found to release the substrate more quickly and induce apoptosis of HL60 cells more effectively than 2a. an expectation of using their cell recognition abilities, lactose, galactose and mannose modified 2-nitrobenzyl derivatives 2b-d were synthesized and their photochemical as well as immunological activities were tested.
A caged Leu-Leu-OMe having a steroid skeleton at 5-hydroxyl of 2-nitrobenzyl 5 was designed and synthesized in an attempt to make use of the phagocytosis function of macrophages towards phosphatidylserine containing liposomes. 5 showed satisfactory characteristics as a caged compound.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (18 results)

All Other

All Publications (18 results)

  • [Publications] Odaka, M., Furuta, T., Kobayashi, Y.and Iwamura, M.: "Synthesis,Phtoreactivity and Cytotoxic Activity of Caged Compounds of L-Leucyl-L-Leucine Methyl Ester,an Apoptosis Inducer." Photochem.Photobiol.63. 800-806 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Iwamura, M.et al.: "Acyloxycoumarinylmethyl-Caged cAMP,the Photolabile and Membrane-Permeable Derivative of cAMP" Biochem.Biophys.Res.Commun.228. 193-198 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Furuta, T., Takeuchi, K.and Iwamura, M.: "Activation of selenoglycosides by photoinduced electron transfer." Chem.Commun.1996. 157-158 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Sakauchi, H., Furuta, T., Kobayashi, Y.and Iwamura, M.: "Synthesis and Cytotoxic Studies of 5-O-(β-Glucopyranosyl)-2-nitrobenzyl Caged L-Leucyl-L-Leucine Methyl Ester with IncreasedSolubility in PBS" Biochem.Biophys.Res.Commun.233. 211-215 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Watanabe, S.and Iwamura, M.: "A Liposome-Forming Caged Compound : Synthesis and Photochemical Properties of a Caged L-Leucyl-L-leucine Methyl Ester with a Steroid Skelton." J.Org.Chem.62. 8616-8617 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Furuta, T., and Iwamura, M.: "New CagedGroups : 7-Substituted Coumarinylmethyl Phosphate Esters." Methods in Enzymol.291. 50-63 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Odaka, M., Furuta, T., Kobayashi, Y.and Iwamura, M.: "Synthesis, Photoreactivity and Cytotoxic Activity of Caged Compounds of L-Leucyl-L-Leucine Meyhy1 Ester, an Apoptosis Inducer." Photochem. Photobiol.63. 800-806 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Furuta, T., Momotaka, A., Sugimoto, M., Hatayama, M., Torigai, H.and Iwamura, M.: "Acyloxycoumarinylmethy1-Caged cAMP,the Photo-labile and Membrane-Permeable Derivative of cAMP That Effectively Stimulates Pigment-Dispersion Responce of Melanophores." Biochem.Biophys.Res.Commun.228. 193-198 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Furuta, T., Takeuchi, K.and Iwamura, M.: "Acivation of selenoglycosides by photoinduced electron transfer." Chem.Commun.1996. 157-158 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Sakauchi, H., Furuta, T., Kobayashi, Y.and Iwamura, M.: "Synthesis and Cytotoxic Studies of 5-O- (beta-Glucopyranosyl) -2-nitrobenzyl Caged L-Leucyl-L-Leucine Methyl Ester with Increased Solubility in PBS Containing 1%DMSO." Biochem.Biophys.Res.Commun.233. 211-215 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Watanade, S.and Iwamura, M.: "A Liposome-Forming Caged Compound : Synthesis and Photochemical Properties of a Caged L-Leucyl-L-leucine MethylEster with a Steroid Skeleton." J.Org.Chem.62. 8616-8617 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Furuta, T., and Iwamura, M.: "New CagedGroups : 7-Substituted Coumarinylmethyl Phosphate Esters." Methods in Enzymol.(G.Marriott., Ed., Academic Press ; New York). 291. 50-63 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Sakauchi,H., Furuta,T., Kobayashi,Y.and Iwamura,M.: "Synthesis and Cytotoxic Studies of 5-O-(β-Glucopyranosyl)-2-nitrobenzyl Caged L-Leucyl-L-Leucine Methyl Ester with Increased Solubility in PBS" Biochem.Biophys.Res.Commun.233. 211-215 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Watanabe,S.and Iwamura,M.: "A Liposome-Forming Caged Compound:Synthesis and Photochemical Properties of a Caged L-Leucyl-L-leucine Methyl Ester with a Steroid Skeleton." J.Org.Chem.62. 8616-8617 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Furuta,T., and Iwamura,M.: "New Caged Croups:7-Substituted Coumarinylmethyl Phosphate Esters." Methods in Enzymol.291. 50-63 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] ODAKA,Furuta,Kobayashi,IWAMURA: "Synthesis,photorenativity and cytotoxic Activity of caged compormds of L-Leucyl-L-Leucine Methyl Ester,an Apoptosis Inducer" phtochemisty of photsbiology. 63(6). 800-806 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Furuta,Momotake,Sugimoto,Torigai,Hatayama,IWAMURA: "Acyloxycouonarinyl methyl caged CAMP,the photalabile and Mombrane-Pelmeable Derivative of cAMP that stimulates Pigment-Dispeision Responce" Biochemical and Biophysical Research Commun.228. 193-198 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Sakauchi,Furuta,Kobayashi,Iwamura: "Synthesis of cytotoxic studies of 5-O-(β-Glucopyranosyl)-2-Nitrobenzyl caged L-Leucyl-L-leucine Methyl Ester." Biochemical and Biophysical Res. Commun.(in press). (1997)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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