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An Azido-BODIPY Probe for Glycosylation: Initiation of Strong Fluorescence upon Triazole Formation

Shie, Jiun-Jie, Liu, Ying-Chih, Lee, Yu-Ming, Lim, Carmay, Fang, Jim-Min, Wong, Chi-Huey
Journal of the American Chemical Society 2014 v.136 no.28 pp. 9953-9961
alkynes, copper, cycloaddition reactions, fluorescence, gel electrophoresis, glycoproteins, glycosylation, image analysis, triazoles, wavelengths
We have designed a low fluorescent azido-BODIPY-based probe AzBOCEt (Az10) that undergoes copper(I)-catalyzed 1,3-dipolar cycloadditions with alkynes to yield strongly fluorescent triazole derivatives. The fluorescent quantum yield of a triazole product T10 is enhanced by 52-fold as compared to AzBOCEt upon excitation at a wavelength above 500 nm. Quantum mechanical calculations indicate that the increase in fluorescence upon triazole formation is due to the lowering of the HOMO energy level of the aryl moiety to reduce the process of acceptor photoinduced electron transfer. AzBOCEt is shown to label alkyne-functionalized proteins in vitro and glycoproteins in cells with excellent selectivity, and enables cell imaging and visualization of glycoconjugates in alkynyl-saccharide-treated cells at extremely low concentration (0.1 μM). Furthermore, the alkyne-tagged glycoproteins from cell lysates can be directly detected with AzBOCEt in gel electrophoresis.