6533b827fe1ef96bd1287236
RESEARCH PRODUCT
Straightforward synthesis of bioconjugatable azo dyes. Part 1: Black Hole Quencher-1 (BHQ-1) scaffold
Pierre-yves RenardAnthony RomieuAnthony RomieuArnaud Chevaliersubject
chemistry.chemical_classificationPhosphoramiditeBioconjugation[CHIM.ORGA]Chemical Sciences/Organic chemistryCarboxylic acidOrganic ChemistryAlkyneBlack Hole Quencher-1[CHIM.CATA]Chemical Sciences/Catalysis[CHIM.THER]Chemical Sciences/Medicinal ChemistryPhotochemistry7. Clean energyBiochemistryFluorescence[CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistrychemistry.chemical_compoundFörster resonance energy transferchemistry[CHIM.ANAL]Chemical Sciences/Analytical chemistryDrug DiscoveryMaleimideComputingMilieux_MISCELLANEOUS[CHIM.CHEM]Chemical Sciences/Cheminformaticsdescription
Abstract Azo dyes are currently used to quench the fluorescence of energy donors in bioassays through Forster resonance energy transfer (FRET) phenomenon. Common examples of such dark quenchers are DABCYL and the three members of Black Hole Quencher® (BHQ) family. Yet, only carboxylic acid and phosphoramidite derivatives of such azo dyes are presently commercially available. This Letter presents a straightforward synthesis method to novel bioconjugatable quenchers derived from BHQ-1 scaffold and equipped with a reactive group being either azido, terminal alkyne, or maleimide. The potential utility of the ‘clickable’ azido and thiol-reactive derivatives was notably demonstrated through the preparation of the first water-soluble BHQ-1 dye and a FRET-based probe suitable for the detection of urokinase-type plasminogen activator (uPA), a key protease in cancer invasion and metastasis, respectively.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-12-10 |