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. 2006 Nov 8;128(44):14224-5.
doi: 10.1021/ja064686s.

Colchicine glycorandomization influences cytotoxicity and mechanism of action

Aqeel Ahmed  1 , Noël R Peters, Megan K Fitzgerald, James A Watson Jr, F Michael Hoffmann, Jon S Thorson
Affiliations

Colchicine glycorandomization influences cytotoxicity and mechanism of action

Aqeel Ahmed et al. J Am Chem Soc. .

Abstract

The reaction of 70 unprotected, diversely functionalized free reducing sugars with methoxyamine-appended colchicine led to the production of a 58-member glycorandomized library. High-throughput cytotoxicity assays revealed glycosylation to modulate specificity and potency. Library members were also identified which, unlike the parent natural product (a destabilizer), stabilized in vitro tubulin polymerization in a manner similar to taxol. This study highlights a simple extension of neoglycorandomization toward amine-bearing scaffolds and the potential benefit of glycosylating nonglycosylated natural products.

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