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Novel mimics of sialyl Lewis X: design, synthesis and biological activity of a series of 2- and 3-malonate substituted galactoconjugates.

Abstract：

:A series of potent inhibitors of P-selectin as potential anti-inflammatory agents is reported. These compounds are derivatives of galactocerebrosides bearing a malonate side chain in positions 2 and 3 of the galactose moiety. Based on the binding mode of sialyl Lewis X, the two acidic groups of the malonate are designed to form ionic interactions with two important lysines in the active site of P-selectin, Lys113 and Lys111. On the other hand, the 4- and 6-hydroxy groups on the galactose ring are arranged to chelate the calcium ion in the P-selectin active site. The synthesis and the biological activity of this series of compounds are described. Lead compounds having a greater potency than sialyl Lewis X are identified.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Marinier A,Martel A,Bachand C,Plamondon S,Turmel B,Daris JP,Banville J,Lapointe P,Ouellet C,Dextraze P,Menard M,Wright JJ,Alford J,Lee D,Stanley P,Nair X,Todderud G,Tramposch KM

doi

10.1016/s0968-0896(01)00015-3

subject

Has Abstract

pub_date

2001-06-01 00:00:00

pages

1395-427

issue

6

eissn

0968-0896

issn

1464-3391

pii

S0968089601000153

journal_volume

9

pub_type

杂志文章

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