title: A comparative study of the self-immolation of para-aminobenzylalcohol and hemithioaminal-based linkers in the context of protease-sensitive fluorogenic probes.
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.
authors.affiliation: Equipe de Chimie Bio-Organique, COBRA-CNRS UMR 6014 & FR 3038, rue Lucien Tesnière, 76131, Mont-Saint-Aignan, France.
authors.forename: Yves
authors.initials: Y
authors.lastname: Meyer
authors.forename: Jean-Alexandre
authors.initials: JA
authors.lastname: Richard
authors.forename: Bruno
authors.initials: B
authors.lastname: Delest
authors.forename: Pauline
authors.initials: P
authors.lastname: Noack
authors.forename: Pierre-Yves
authors.initials: PY
authors.lastname: Renard
authors.forename: Anthony
authors.initials: A
authors.lastname: Romieu
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry* / Q000378:metabolism; D001592:Benzyl Alcohols / Q000737:chemistry* / Q000378:metabolism; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000378:metabolism*; D006038:Glyoxylates / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D010447:Peptide Hydrolases / Q000378:metabolism*
chemical_list: D001547:Benzaldehydes; D001592:Benzyl Alcohols; D005456:Fluorescent Dyes; D006038:Glyoxylates; C033525:4-carboxybenzaladehyde; D010447:Peptide Hydrolases; C031150:glyoxylic acid