Organic & Biomolecular Chemistry 2010-04-21

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

Yves Meyer, Jean-Alexandre Richard, Bruno Delest, Pauline Noack, Pierre-Yves Renard, Anthony Romieu

Index: Org. Biomol. Chem. 8(8) , 1777-80, (2010)

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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.