Design and synthesis of a new sialyl Lewis X mimetic: how selective are the selectin receptors?

M De Vleeschauwer; M Vaillancourt; N Goudreau; Y Guindon; D Gravel

doi:10.1016/s0960-894x(01)00130-5

Design and synthesis of a new sialyl Lewis X mimetic: how selective are the selectin receptors?

Bioorg Med Chem Lett. 2001 May 7;11(9):1109-12. doi: 10.1016/s0960-894x(01)00130-5.

Authors

M De Vleeschauwer¹, M Vaillancourt, N Goudreau, Y Guindon, D Gravel

Affiliation

¹ Départment de chimie, Université de Montréal, Québec, Canada.

PMID: 11354355
DOI: 10.1016/s0960-894x(01)00130-5

Abstract

The present paper reports the molecular modeling-based design and synthesis of an optically pure noncarbohydrate mimetic of sialyl Lewis X to inhibit E-selectin. Biological evaluation of the designed substance as well as that of its enantiomer gave, contrary to expectations, comparable IC50 values. Results are discussed in terms of receptor binding specificity and the molecular modeling protocol used.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Sequence
E-Selectin / drug effects*
Models, Molecular
Molecular Mimicry
Molecular Sequence Data
Oligosaccharides / chemistry*
Receptors, Lymphocyte Homing / drug effects*
Sialyl Lewis X Antigen
Stereoisomerism

Substances

E-Selectin
Oligosaccharides
Receptors, Lymphocyte Homing
Sialyl Lewis X Antigen