Studies on selectin blocker. 3. Investigation of the carbohydrate ligand sialyl Lewis X recognition site of P-selectin

Yasuyuki Hiramatsu, Hideki Tsujishita, Hirosato Kondo

研究成果: ジャーナルへの寄稿学術誌査読

24 被引用数 (Scopus)

抄録

We have previously found that a 1-deoxy sialyl Lewis X (3), which lacks only the C-1 hydroxyl group of sialyl Lewis X (sLe(X)), exhibited up to 20 times more potency than the sLe(X) toward P-selectin binding. In order to explain the structure-activity relationship, we constructed structural models of the complexes of P-selectin and compounds 1-3 and sLe(X). From the modeling analysis, we found that the carbonyl oxygen of the N-acetyl group of GlcNAc in 3 formed a hydrogen bond with the amide group of Asn 82 in P- selectin. We also supposed that there was a hydrophobic interaction between the pyranose of GlcNAc in compound 3 and the imidazole ring of His 108 in P- selectin. However, it is considered that those interactions would not be appreciable in the case of sLe(X) or other 1-deoxy sLe(X) analogs (1,2). Accordingly, our results could be helpful in obtaining a new concept to design a potent inhibitor toward P-selectin binding.

本文言語英語
ページ(範囲)4547-4553
ページ数7
ジャーナルJournal of Medicinal Chemistry
39
23
DOI
出版ステータス出版済み - 11月 26 1996
外部発表はい

!!!All Science Journal Classification (ASJC) codes

  • 分子医療
  • 創薬

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