title: An azido-BODIPY probe for glycosylation: initiation of strong fluorescence upon triazole formation.
abstract: 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.
authors: The Genomics Research Center, Academia Sinica , Taipei 11529, Taiwan.
authors: Jiun-Jie
authors: JJ
authors: Shie
authors: Ying-Chih
authors: YC
authors: Liu
authors: Yu-Ming
authors: YM
authors: Lee
authors: Carmay
authors: C
authors: Lim
authors: Jim-Min
authors: JM
authors: Fang
authors: Chi-Huey
authors: CH
authors: Wong
mesh_terms: D001386:Azides / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D045744:Cell Line, Tumor; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D005456:Fluorescent Dyes / Q000737:chemistry*; D006023:Glycoproteins / Q000737:chemistry / Q000378:metabolism; D006031:Glycosylation; D006801:Humans; D008175:Lung Neoplasms / Q000473:pathology; D014230:Triazoles / Q000138:chemical synthesis*
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001386:Azides; D001896:Boron Compounds; D005456:Fluorescent Dyes; D006023:Glycoproteins; D014230:Triazoles; D003300:Copper