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Developmental Research for New Medicines Based on Carbohydrate-cell Recognition

Research Project

Project/Area Number 05556019
Research Category

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

Allocation TypeSingle-year Grants
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionGifu University

Principal Investigator

KISO Makoto  Gifu University, Professor, 農学部, 教授 (90092931)

Co-Investigator(Kenkyū-buntansha) YOSHIKUNI Yoshiaki  Nippon Shinyaku Co.Ltd., Head of Research Labo., 生物研究所, 部長
ISHIDA Hideharu  Gifu University, Assoc.Professor, 農学部, 助教授 (20203002)
HASEGAWA Akira  Gifu University, Professor, 農学部, 教授 (10026429)
Project Period (FY) 1993 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥7,800,000 (Direct Cost: ¥7,800,000)
Fiscal Year 1995: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1994: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1993: ¥6,600,000 (Direct Cost: ¥6,600,000)
Keywords1-deoxynojirimycin / cell adhesion inhibitor / sialyl-Lewis X oligosaccharide / sialyl-Lewis A oligosaccharide / sulfo-Lewis X oligosaccharide / sulfo-Lewis A oligosaccharide / 1-デオキシノジリマイシン / セレクチン結合阻害剤 / 糖鎖医薬品 / N-アルキル-1-デオキシノジリマイシン / シアリルオリゴサッカライド / シアリルルイス X / シアリルルイス A / N-メチル-1-デオキシノジリマイシン / シアロ糖鎖 / シアリルルイスX / シアリルルイスA / セレクチン
Research Abstract

We have examined the recognition specificity of sialooligosaccharides by influenza virus and leukocyte cell adhesion molecules (selectin family) at the molecular level. As a results, it has been shown that 1) sialyl paragloboside is one of the best substrate for influenza virus recognition, and 2) both sialyl-Lewis X and sialyl-Lewis A can be well recognized by all selectins. It was also found that sulfo-Lewis X and sulfo-Lewis A function as the selectin ligands with the equal or more afinity than the corresponding sialyl derivatives.
Based on these results, a variety of novel oligosaccharides containing 1-deoxynojirimycin have been synthesized as the inhibitors of virus infection and selectin binding. Some of the N-alkyl-1-deoxynojirimycin-containing sialyl-and sulfo-Lewis X and -Lewis A epitope analogs have been found to be potent anti-inflammatory agents by using the animal models. A wide therapeutic application of these compounds is now in progress.

Report

(4 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • 1993 Annual Research Report
  • Research Products

    (40 results)

All Other

All Publications (40 results)

  • [Publications] M.Kiso: "Synthesis of novel N-methyl-1-deoxynojirimycin-containing sialooligosaccharides related to ganglioside GM3 active as a biosignal mediator." J.Carbohydr.Chem.13. 175-191 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Kiso: "Systematic synthesis of N-methyl-1-deoxynojirimycin-containing, Le^x, Le^a, sialyl-Le^x and sialyl-Le^a epitopes recognized by selectins." Bioorganic & Medicinal Chem.2. 1295-1308 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S.Ladisch: "Immunosuppressive activity of chemically synthesized gangliosides." Biochemistry. 34. 1197-1202 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.S.Mulligan: "Anti-inflammatory effects of sulphatides in selectin-dependent acute lung injury." International Immunology. 7. 1107-1113 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Kiso: "Synthetic and structural studies of α-sialyl- (2-6) and α-sialyl- (2-3) 1-deoxynojirimycin derivatives potentially useful for biomedical applications." Carbohydr. Res.272. 159-178 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Kiso: "Studies on selectin binding inhibitors: synthesis of sialyl-Le^x and sialyl-Le^a epitope analogs containing 2-acetamido derivative of N-methyl-1-deoxynojirimycin." J.Carbohydr.Chem.15. (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Kiso: "Neoglycoconjugates, Methods in Enzymology Vol.242" Academic Press, 328 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 木曽 真 他: "ガングリオシド研究法I" 学会出版センター, 259 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Brandley, B.K., Kiso, M., Hasegawa, A.et al: "Structure-function studies on selectin carbohydrate ligands. Modification to fucose, sialic acid and sulphate as a sialic acid replacement." Glycobiology. 3. 633-639 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kiso, M.et al.: "Synthesis of novel N-methyl-1-deoxynojirimycin-containing sialooligosaccharides related to ganglioside GM3 active as a biosignal mediator" J.Carbohydr.Chem.13. 175-191 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kiso, M.et al.: "Systematic synthesis of N-methyl-1-deoxynojirimycin-containing, Lex, Lea, sialyl-Lex and sialyl-Lea epitopes recognized by selectins" Bioorganic & Medicinal Chem.2. 1295-1308 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Ladisch, S., Hasegawa, A., Kiso, M.et al.: "Immunosuppressive activity of chemically synthesized gangliosides" Biochemistry. 34. 1197-1202 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Mulligan, M.S., Kiso, M., Hasegawa, A.et al.: "Anti-inflammatory effects of sulphatides in selectin-dependent acute lung injury" International Immunology. 7. 1107-1113 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kiso, M.et al.: "Synthetic and structural studies of alpha-sialyl-(2-6) and alpha-sialyl-(2-3) 1-deoxynojirimycin derivatives potentially useful for biomedical applications" Carbohydr.Res.272. 159-178 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kiso, M.et al.: "Studies on selectin binding inhibitors : synthesis of sialyl-Lex and sialyl-Lea epitope analogs containing 2-acetamido derivative of N-methyl-1-deoxynojirimycin" J.Carbohydr.Chem.15 (in press). (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kiso, M.et al.: "Synthesis of sialyl Lewis X ganglioside and analogs. in Neoglycilipids" Methods in Enzymol.242. 158-173 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] "Synthesis of ganglioside GM3 and analogs contain modified sialic acids and ceramides" Methods in Enzymol.242. 173-183 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S.Ladisch: "Immunosuppressive activity of chemically synthesized ganglioside" Biochemistry. 34. 1197-1202 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] A.Hasegawa: "Synthesis of sialyl and sulfo Lewis X analogs containing a ceramide or 2-(tetradecyl)hexadecyl residue." J. Carbohydr. Chem.14. 353-368 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Maeda: "Synthesis of sulfo- and sialyl-Lewis X epitope analogs containing the 1-deoxy-N-acetylglucosamine." J. Carbohydr. Chem.14. 369-385 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Maeda: "Synthesis of sulfo-, phosphono- and sialyl-Lewis X analogs containing the 1-deoxy- and 1,2-dideoxyhexopyranoses." J. Carbohydr. Chem.14. 387-406 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Kiso: "Synthetic and structural studies of α-sialyl-(2-6) and α-sialyl-(2-3) 1-deoxynojirimycin derivatives potentially useful for" Carbohydr. Res.272. 159-178 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Kiso: "Studies on selectin binding inhibitors: synthesis of sialyl-Le^x sialyl-Le^a epitope analogs containing 2-acetamido derivative of" J. Carbohydr. Chem.15(in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] 木曽真: "ガングリオシド研究法I" 学会出版センター, 259 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] A.Hasegawa: "Carbohydrates: Targets for Rational Drug Design" Marcel Dekker Inc. New York, NY, 250 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Kiso: "Synthesis of novel N-methyl-1-deoxynojirimycin-containing sialo-o1igosaccharides related to ganglioside GM3 active as a biosign" J.Carbohydr.Chem. 13. 175-191 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Kiso: "Systematic synthesis of N-methyl-1-deoxynojirimycin-containing,Lex,Lea,sialyl-Lex and sialyl-Lea epitopes" Bioorganic & Medicinal Chemistry. 2. 1295-1308 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] A.Kondo: "An efficient structural analysis of N-methyl-1-deoxynojirimycin-containing sialo-01igosaccharides by ion-spray MS" J.Carbohydr.Chem. 13. 545-554 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] A.Hasegawa: "Synthesis of deoxy-L-fucose-containing sialyl Lewis X" Carbohydr.Res.257. 67-80 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] G.Xu: "Specificity of sialyl-sugar chain mediated recognitionby the hemagglutinin of human influenza B vitus isolates" J.Biochem,. 115. 202-207 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ladisch: "A chemically synthesized sialic acid-containing glycoconjugate is a potent inhibitor of cellular immune responses" Biochem.Biophys.Res.Commun.203. 1102-1109 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Kiso: "Neoglycoconjugates,Methods in Enzymology Vo1.242" Academic Press, 328 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 岩瀬仁勇: "糖鎖の科学入門" 培風館, 215 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Kiso: "Synthesis of 1-deoxynojirimycin-containing oligosaccharides related to the cancer-associated sialyl-Lewis A antigen" J.Carbohydr.Chem.12. 673-677 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] M.Kiso: "Novel disaccharides and lactams composed of sialic acid and 1-deoxynojirimycin,potential for biomedical application" J.Carbohydr.Chem.12. 985-990 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] M.Yoshida: "Synthesis of chemically modified sialic acid-containing sialyl-Lewis X ganglioside analogues recognized by the selectin family" Glycoconjugate J.10. 3-15 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Y.Suzuki: "Sulfated glycolipids are ligands for a lymphocyte homing receptor L-selectin (LECAM-1),binding epitope in sulfated sugar chain" Biochem.Biophys.Res.Commun.190. 426-434 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] G.Xu: "Drift of the sialyl-linkage specific recognition of the sialidase of influenza B virus isolates" J.Biochem.113. 304-307 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] A.Takada: "Contribution of carbohydrate antigens sialyl Lewis A and sialyl Lewis X to adhesion of human cancer cells to vascular endothelium" Cancer Res.53. 354-361 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] 長谷川明: "糖質エンジニアリングと製品化技術" サイエンスフォーラム, 303 (1993)

    • Related Report
      1993 Annual Research Report

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

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