Studies on selectin blocker. 1. Structure-activity relationships of sialyl Lewis X analogs

Hiroshi Ohmoto, Kenji Nakamura, Tomomi Inoue, Noriko Kondo, Yoshimasa Inoue, Kohichiro Yoshino, Hirosato Kondo, Hideharu Ishida, Makoto Kiso, Akira Hasegawa

Research output: Contribution to journalReview article

63 Citations (Scopus)

Abstract

As a part of our studies of selectin blockers, we prepared 1-deoxy-3'-O- sulfo Le(x) analogs (1-3), 1-deoxy-3'-O-phosphono Le(x) analogs (4), and 1- deoxy sLe(x) analogs (5-7), and examined their inhibitory activities against natural ligand (sLe(x)) binding to E-selectin, P-selectin, and L-selectin. The 1-deoxy sLe(x) 5 was up to 20 times more potent an inhibitor than the sLe(x) tetrasaccharide toward P- and L-selectin binding. This indicates that the modification of the 1 or 2 position of sLe(x) is useful in the design of a more potent selectin blocker.

Original languageEnglish
Pages (from-to)1339-1343
Number of pages5
JournalJournal of Medicinal Chemistry
Volume39
Issue number6
DOIs
Publication statusPublished - Mar 15 1996
Externally publishedYes

Fingerprint

L-Selectin
Selectins
P-Selectin
Structure-Activity Relationship
E-Selectin
Ligands
3-sulfated Lewis x

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

Ohmoto, H., Nakamura, K., Inoue, T., Kondo, N., Inoue, Y., Yoshino, K., ... Hasegawa, A. (1996). Studies on selectin blocker. 1. Structure-activity relationships of sialyl Lewis X analogs. Journal of Medicinal Chemistry, 39(6), 1339-1343. https://doi.org/10.1021/jm9506478

Studies on selectin blocker. 1. Structure-activity relationships of sialyl Lewis X analogs. / Ohmoto, Hiroshi; Nakamura, Kenji; Inoue, Tomomi; Kondo, Noriko; Inoue, Yoshimasa; Yoshino, Kohichiro; Kondo, Hirosato; Ishida, Hideharu; Kiso, Makoto; Hasegawa, Akira.

In: Journal of Medicinal Chemistry, Vol. 39, No. 6, 15.03.1996, p. 1339-1343.

Research output: Contribution to journalReview article

Ohmoto, H, Nakamura, K, Inoue, T, Kondo, N, Inoue, Y, Yoshino, K, Kondo, H, Ishida, H, Kiso, M & Hasegawa, A 1996, 'Studies on selectin blocker. 1. Structure-activity relationships of sialyl Lewis X analogs', Journal of Medicinal Chemistry, vol. 39, no. 6, pp. 1339-1343. https://doi.org/10.1021/jm9506478
Ohmoto, Hiroshi ; Nakamura, Kenji ; Inoue, Tomomi ; Kondo, Noriko ; Inoue, Yoshimasa ; Yoshino, Kohichiro ; Kondo, Hirosato ; Ishida, Hideharu ; Kiso, Makoto ; Hasegawa, Akira. / Studies on selectin blocker. 1. Structure-activity relationships of sialyl Lewis X analogs. In: Journal of Medicinal Chemistry. 1996 ; Vol. 39, No. 6. pp. 1339-1343.
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AU - Ohmoto, Hiroshi

AU - Nakamura, Kenji

AU - Inoue, Tomomi

AU - Kondo, Noriko

AU - Inoue, Yoshimasa

AU - Yoshino, Kohichiro

AU - Kondo, Hirosato

AU - Ishida, Hideharu

AU - Kiso, Makoto

AU - Hasegawa, Akira

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AB - As a part of our studies of selectin blockers, we prepared 1-deoxy-3'-O- sulfo Le(x) analogs (1-3), 1-deoxy-3'-O-phosphono Le(x) analogs (4), and 1- deoxy sLe(x) analogs (5-7), and examined their inhibitory activities against natural ligand (sLe(x)) binding to E-selectin, P-selectin, and L-selectin. The 1-deoxy sLe(x) 5 was up to 20 times more potent an inhibitor than the sLe(x) tetrasaccharide toward P- and L-selectin binding. This indicates that the modification of the 1 or 2 position of sLe(x) is useful in the design of a more potent selectin blocker.

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