Straightforward synthesis of bioconjugatable azo dyes. Part 1: Black Hole Quencher-1 (BHQ-1) scaffold |
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| Affiliation: | 1. Normandie Univ, COBRA, UMR 6014 & FR 3038, UNIV Rouen; INSA Rouen; CNRS, IRCOF, 1 Rue Tesnières, 76821 Mont-Saint-Aignan Cedex, France;2. ICMUB, UMR CNRS 6302, Université de Bourgogne, 9, Avenue Alain Savary, 21078 Dijon, France;3. Institut Universitaire de France, 103 Boulevard Saint-Michel, 75005 Paris, France;1. School of Chemistry and Chemical Engineering, Hunan Institute of Engineering, Xiangtan 411104, China;2. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China;1. Key Laboratory for Green Chemical Process of the Ministry of Education, School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan, PR China;2. The United Innovation of Mengchao Hepatobiliary Technology Key Laboratory of Fujian Province, Mengchao Hepatobiliary Hospital of Fujian Medical University, Fuzhou 350025, PR China |
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| Abstract: | Azo dyes are currently used to quench the fluorescence of energy donors in bioassays through Förster 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. |
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| Keywords: | Activatable probes Azo dyes Bioconjugation Dark quenchers FRET |
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