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RESEARCH PRODUCT
In situ formation of pyronin dyes for fluorescence protease sensing
Anthony RomieuAnthony RomieuSylvain Debieusubject
In situStereochemistrymedicine.medical_treatment010402 general chemistryalkaline-phosphatase activity01 natural sciencesBiochemistryAminopeptidaseFluorescenceMass SpectrometryIn vivo[ CHIM.ORGA ] Chemical Sciences/Organic chemistryhydrogen-sulfidemedicinePyronineturn-on chemodosimeterPhysical and Theoretical ChemistryChromatography High Pressure Liquidlarge stokes shiftFluorescent DyesProteaseMolecular Structure[CHIM.ORGA]Chemical Sciences/Organic chemistry010405 organic chemistryChemistryOrganic ChemistryFluorescence0104 chemical sciences3. Good healthselective detectionPenicillin G Acylasefluorogenic probesplacental leucine aminopeptidasesensitive detectioncascade reactionLeucineliving cellsPeptide Hydrolasesdescription
International audience; 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-03-28 |