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J. Biol. Chem., Vol. 269, Issue 31, 19663-19666, Aug, 1994
BN Rao, MB Anderson, JH Musser, JH Gilbert, ME Schaefer, C Foxall and BK Brandley
The selectins, a family of adhesion receptors involved in leukocyte
extravasation, recognize sialyl Lewis X (sLe(x); NeuAc alpha 2-3Gal beta
1-4(Fuc alpha 1-3)GlcNAc) and related oligosaccharides. We used
conformational energy computations, high field NMR, and structure- function
studies to define distance parameters of critical functional groups of
sLe(x). This sLe(x) pharmacophore was used to search a three- dimensional
data base of chemical structures. Compounds that had a similar spatial
relationship of functional groups were tested as inhibitors of selectin
binding. Glycyrrhizin, a triterpene glycoside, was identified and found to
block selectin binding to sLe(x) in vitro. We substituted different sugars
for the glucuronic acids of glycyrrhizin and found the L-fucose derivative
to be the most active in vitro and in vivo. A C-fucoside derivative,
synthesized on a linker designed for stability and to more closely
approximate the original sLe(x) pharmacophore, resulted in an easily
synthesized, effective selectin blocker with anti-inflammatory activity.
Sialyl Lewis X mimics derived from a pharmacophore search are selectin inhibitors with anti-inflammatory activity
Glycomed Inc., Alameda, California 94501.
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