Issue 22, 2012

New insights into the water-solubilisation of fluorophores by post-synthetic “click” and Sonogashira reactions

Abstract

New synthetic methodologies for the efficient chemical conversion of hydrophobic fluorescent dyes into bioconjugable and water-soluble derivatives are described. The combined use of an original sulfonated terminal alkyne and a metal-mediated reaction, namely the copper-catalysed Huisgen 1,3-dipolar cycloaddition (“click” reaction) or the Sonogashira cross-coupling, is the cornerstone of these novel post-synthetic sulfonation approaches.

Graphical abstract: New insights into the water-solubilisation of fluorophores by post-synthetic “click” and Sonogashira reactions

Supplementary files

Article information

Article type
Communication
Submitted
27 Feb 2012
Accepted
17 Apr 2012
First published
18 Apr 2012

Org. Biomol. Chem., 2012,10, 4330-4336

New insights into the water-solubilisation of fluorophores by post-synthetic “click” and Sonogashira reactions

C. Massif, S. Dautrey, A. Haefele, R. Ziessel, P. Renard and A. Romieu, Org. Biomol. Chem., 2012, 10, 4330 DOI: 10.1039/C2OB25428J

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