Issue 22, 2012
From the journal:

Organic & Biomolecular Chemistry

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

Cédrik Massif,a   Sébastien Dautrey,a   Alexandre Haefele,b   Raymond Ziessel,b   Pierre-Yves Renardacd  and  Anthony Romieu*acd  

* Corresponding authors

a Université de Rouen, Laboratory COBRA UMR 6014 and FR 3038, IRCOF, 1 Rue Tesnière, 76821 Mont St Aignan Cedex, France
E-mail: anthony.romieu@univ-rouen.fr
Fax: + 33 (0)2 35 52 29 71
Tel: + 33 (0)2 35 52 24 27

b Laboratoire de Chimie Moléculaire et Spectroscopies Avancées (LCOSA), Ecole Européenne de Chimie, Polymères et Matériaux, 25 rue Becquerel, 67087 Strasbourg Cedex 02, France
E-mail: ziessel@unistra.fr
Fax: (+) 33 3-68-85-27-61

c INSA de Rouen, Avenue de l'Université, 76800 St Etienne du Rouvray, France

d CNRS Délégation Normandie, 14 Rue Alfred Kastler, 14052 Caen Cedex, France

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

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Article information

DOI
https://doi.org/10.1039/C2OB25428J
Article type
Communication
Submitted
27 Feb 2012
Accepted
17 Apr 2012
First published
18 Apr 2012

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

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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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