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Issue 24, 2011
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A new cyclopamine glucuronide prodrug with improved kinetics of drug release

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Abstract

We prepared a new glucuronide prodrug of cyclopamine designed to target selectively the Hedgehog signalling pathway of cancer cells. This prodrug includes a novel self-immolative linker bearing a hydrophilic side chain that can be easily introduced via “click chemistry”. With this design, the prodrug exhibits reduced toxicity compared to the free drug on U87 glioblastoma cells. However, in the presence of β-glucuronidase, the prodrug conducts to the quick release of cyclopamine thereby restoring its antiproliferative activity.

Graphical abstract: A new cyclopamine glucuronide prodrug with improved kinetics of drug release

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Supplementary files

Article information


Submitted
04 Jul 2011
Accepted
19 Sep 2011
First published
19 Sep 2011

Org. Biomol. Chem., 2011,9, 8459-8464
Article type
Paper

A new cyclopamine glucuronide prodrug with improved kinetics of drug release

B. Renoux, T. Legigan, S. Bensalma, C. Chadéneau, J. Muller and S. Papot, Org. Biomol. Chem., 2011, 9, 8459
DOI: 10.1039/C1OB06081C

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