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

doi:10.1021/jm9506478

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 journal › Review article › peer-review

64 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 language	English
Pages (from-to)	1339-1343
Number of pages	5
Journal	Journal of Medicinal Chemistry
Volume	39
Issue number	6
DOIs	https://doi.org/10.1021/jm9506478
Publication status	Published - Mar 15 1996
Externally published	Yes

All Science Journal Classification (ASJC) codes

Molecular Medicine
Drug Discovery

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10.1021/jm9506478

Cite this

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title = "Studies on selectin blocker. 1. Structure-activity relationships of sialyl Lewis X analogs",

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.",

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

year = "1996",

month = mar,

day = "15",

doi = "10.1021/jm9506478",

language = "English",

volume = "39",

pages = "1339--1343",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "6",

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TY - JOUR

T1 - Studies on selectin blocker. 1. Structure-activity relationships of sialyl Lewis X analogs

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

PY - 1996/3/15

Y1 - 1996/3/15

N2 - 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.

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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U2 - 10.1021/jm9506478

DO - 10.1021/jm9506478

M3 - Review article

C2 - 8632441

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VL - 39

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JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 6

ER -

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

Abstract

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