Issue 8, 2010
From the journal:

Organic & Biomolecular Chemistry

A comparative study of the self-immolation of para-aminobenzylalcohol and hemithioaminal-based linkers in the context of protease-sensitive fluorogenic probes†

Yves Meyer,ab   Jean-Alexandre Richard,ab   Bruno Delest,b   Pauline Noack,b   Pierre-Yves Renard*acd  and  Anthony Romieu*ac  

* Corresponding authors

a Equipe de Chimie Bio-Organique, COBRA-CNRS UMR 6014 & FR 3038, rue Lucien Tesnière, Mont-Saint-Aignan, France
E-mail: pierre-yves.renard@univ-rouen.fr, anthony.romieu@univ-rouen.fr
Fax: +33 2-35-52-29-71
Tel: +33 2-35-52-24-14 (or 24-15)

b QUIDD, Technopôle du Madrillet, 50, rue Ettore Bugatti, Saint-Etienne du Rouvray, France

c Université de Rouen, Place Emile Blondel, Mont-Saint-Aignan, France

d Institut Universitaire de France, 103 Boulevard Saint-Michel, Paris, France

Abstract

This study focuses on the disassembly-behavior of self-immolative pro-fluorescent linkers under physiological conditions and through an enzyme-initiated domino reaction. The targeted linkers are based on para-aminobenzylalcohol (PABA) or hemithioaminal derivatives of para-carboxybenzaldehyde or glyoxilic acid. We found that a fine tuning of the kinetic properties could be obtained through the modulation of the linker structure, giving either a fast signal response or free-adaptable systems suitable for the design of protease-sensitive fluorogenic probes or prodrug systems.

Graphical abstract: A comparative study of the self-immolation of para-aminobenzylalcohol and hemithioaminal-based linkers in the context of protease-sensitive fluorogenic probes

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Article information

DOI
https://doi.org/10.1039/B926316K
Article type
Communication
Submitted
14 Dec 2009
Accepted
24 Feb 2010
First published
08 Mar 2010

Org. Biomol. Chem., 2010,8, 1777-1780

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A comparative study of the self-immolation of para-aminobenzylalcohol and hemithioaminal-based linkers in the context of protease-sensitive fluorogenic probes

Y. Meyer, J. Richard, B. Delest, P. Noack, P. Renard and A. Romieu, Org. Biomol. Chem., 2010, 8, 1777 DOI: 10.1039/B926316K

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