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. 2007 Jul 15;15(14):4951-65.
doi: 10.1016/j.bmc.2007.04.038. Epub 2007 Apr 25.

Synthesis of sialic acid derivatives as ligands for the myelin-associated glycoprotein (MAG)

Sachin V Shelke  1 , Gan-Pan Gao, Stefanie Mesch, Heiko Gäthje, Soerge Kelm, Oliver Schwardt, Beat Ernst
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Synthesis of sialic acid derivatives as ligands for the myelin-associated glycoprotein (MAG)

Sachin V Shelke et al. Bioorg Med Chem. .

Abstract

The trisaccharide substructure 13 of the ganglioside GQ1balpha shows a remarkable affinity for the myelin-associated glycoprotein (MAG). In the search for structurally simplified and pharmacokinetically improved mimics of 13, sialosides with modifications at the reducing and non-reducing end were synthesized. The biological evaluation of mimics 12a-o was performed in a competitive target-based assay. It was found that the relative inhibitory potency (rIP) of antagonist 12h was enhanced by more than 1000-fold in comparison to the reference trisaccharide 13, despite the former having a much simpler structure. In addition, the sialic acid derivatives, for example, 12h, have clearly improved pharmacokinetic properties due to the presence of aromatic moieties, a lower molecular weight, and a reduced number of polar hydroxy functions compared to the reference compound 13.

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