Issue 19, 2009
From the journal:

Organic & Biomolecular Chemistry

Fragment-based development of triazole-substituted O-galactosyl aldoximes with fragment-induced affinity and selectivity for galectin-3†

Johan Tejler,a   Bader Salameh,b   Hakon Lefflerc  and  Ulf J. Nilsson*a  

* Corresponding authors

a Organic Chemistry, Lund University, Lund, Sweden
E-mail: ulf.nilsson@organic.lu.se
Fax: +46 46 2228209
Tel: +46 46 2228218

b Chemistry Department, The Hashemite University, Zarka 13115, Jordan

c Section MIG, Department of Laboratory Medicine, Lund University, Sölvegatan 23, Lund, Sweden

Abstract

A fragment-based development of 3C-triazol-1-yl-O-galactopyranosyl aldoximes led to the discovery of highly selective and high affinity (Kd down to 11 μM) small monosaccharide based inhibitors of galectin-3. Galectin-7, 8 N-terminal CRD, and 9 N-terminal CRD bound the inhibitors only weakly. The galectin-3 selectivity was hypothesized to stem from interaction of the aldoxime moiety with a site not present in the other galectins.

Graphical abstract: Fragment-based development of triazole-substituted O-galactosyl aldoximes with fragment-induced affinity and selectivity for galectin-3

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Article information

DOI
https://doi.org/10.1039/B909091F
Article type
Paper
Submitted
08 May 2009
Accepted
19 Jun 2009
First published
20 Jul 2009

Org. Biomol. Chem., 2009,7, 3982-3990

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Fragment-based development of triazole-substituted O-galactosyl aldoximes with fragment-induced affinity and selectivity for galectin-3

J. Tejler, B. Salameh, H. Leffler and U. J. Nilsson, Org. Biomol. Chem., 2009, 7, 3982 DOI: 10.1039/B909091F

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