title: A Double-Clicking Bis-Azide Fluorogenic Dye for Bioorthogonal Self-Labeling Peptide Tags.
abstract: Herein, we give the very first example for the development of a fluorogenic molecular probe that combines the two-point binding specificity of biarsenical-based dyes with the robustness of bioorthogonal click-chemistry. This proof-of-principle study reports on the synthesis and fluorogenic characterization of a new, double-quenched, bis-azide fluorogenic probe suitable for bioorthogonal two-point tagging of small peptide tags by double strain-promoted azide-alkyne cycloaddition. The presented probe exhibits remarkable increase in fluorescence intensity when reacted with bis-cyclooctynylated peptide sequences, which could also serve as possible self-labeling small peptide tag motifs.
authors.affiliation: Chemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary.
authors.forename: Orsolya
authors.initials: O
authors.lastname: Demeter
authors.affiliation: Chemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary.
authors.forename: Eszter A
authors.initials: EA
authors.lastname: Fodor
authors.affiliation: MTA-BME "Lendület" Quantum Chemistry Research Group, Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, P.O. Box 91, 1521, Budapest, Hungary.
authors.forename: Mihály
authors.initials: M
authors.lastname: Kállay
authors.affiliation: MTA-ELTE Research Group of Peptide Chemistry, Hungarian Academy of Sciences, Pázmány Péter sétány 1 a, 1117, Budapest, Hungary.
authors.forename: Gábor
authors.initials: G
authors.lastname: Mező
authors.affiliation: Chemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary.
authors.forename: Krisztina
authors.initials: K
authors.lastname: Németh
authors.affiliation: MS Metabolomics Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary).
authors.forename: Pál T
authors.initials: PT
authors.lastname: Szabó
authors.affiliation: Chemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary. kele.peter@ttk.mta.hu.
authors.forename: Péter
authors.initials: P
authors.lastname: Kele
mesh_terms: D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D005456:Fluorescent Dyes / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry* / Q000378:metabolism; D013194:Staining and Labeling
chemical_list: D001386:Azides; D005456:Fluorescent Dyes; D009842:Oligopeptides
keywords: click chemistry; cycloaddition; dyes/pigments; fluorescent probes; peptides