%0 Journal Article %T In situ formation of pyronin dyes for fluorescence protease sensing %+ Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon] (ICMUB) %+ Institut Universitaire de France (IUF) %A Debieu, Sylvain %A Romieu, Anthony %Z Institut Universitaire de France (IUF) Burgundy region %< avec comité de lecture %@ 1477-0520 %J Organic & Biomolecular Chemistry %I Royal Society of Chemistry %V 15 %N 12 %P 2575 - 2584 %8 2017-03-28 %D 2017 %R 10.1039/c7ob00370f %K large stokes shift %K placental leucine aminopeptidase %K alkaline-phosphatase activity %K turn-on chemodosimeter %K fluorogenic probes %K living cells %K sensitive detection %K hydrogen-sulfide %K selective detection %K cascade reaction %Z Chemical Sciences/Organic chemistryJournal articles %X We report a reaction-based strategy for the fluorogenic detection of protease activity. Based on the "covalent-assembly" probe design principle recently put forward by the Yang group for detection of Sarin related threats (J. Am. Chem. Soc., 2014, 136, 6594-6597), we have designed two unusual nonfluorescent caged precursors (mixed bis-aryl ethers) which are readily converted into a fluorescent unsymmetrical pyronin dye through a domino cyclisation-aromatisation reaction triggered by penicillin G acylase (PGA) or leucine aminopeptidase (LAP). Fluorescence-based in vitro assays and HPLCfluorescence/- MS analyses support the claimed activation mechanism whose the further implementation to "smart" imaging agents for the study of protease function in vivo is expected. %G English %2 https://u-bourgogne.hal.science/hal-01522066/document %2 https://u-bourgogne.hal.science/hal-01522066/file/Debieu-2017-Postprint.pdf %L hal-01522066 %U https://u-bourgogne.hal.science/hal-01522066 %~ UNIV-BOURGOGNE %~ CNRS %~ ICMUB %~ INC-CNRS %~ TEST-HALCNRS %~ TEST2-HALCNRS