Bioconjugate Chemistry
Bioconjugate Chemistry
5 years ago

Bisazide Cyanine Dyes as Fluorogenic Probes for Bis-Cyclooctynylated Peptide Tags and as Fluorogenic Cross-Linkers of Cyclooctynylated Proteins

Bisazide Cyanine Dyes as Fluorogenic Probes for Bis-Cyclooctynylated Peptide Tags and as Fluorogenic Cross-Linkers of Cyclooctynylated Proteins
Christine Koehler, Gábor Mező, Orsolya Demeter, Péter Kele, Attila Kormos, Krisztina Németh, Eszter Kozma, Edward A. Lemke, Levente B. Takács
Herein we present the synthesis and fluorogenic characterization of a series of double-quenched bisazide cyanine probes with emission maxima between 565 and 580 nm that can participate in covalent, two-point binding bioorthogonal tagging schemes in combination with bis-cyclooctynylated peptides. Compared to other fluorogenic cyanines, these double-quenched systems showed remarkable fluorescence intensity increase upon formation of cyclic dye–peptide conjugates. Furthermore, we also demonstrated that these bisazides are useful fluorogenic cross-linking platforms that are able to form a covalent linkage between monocyclooctynylated proteins.

Publisher URL: http://dx.doi.org/10.1021/acs.bioconjchem.7b00178

DOI: 10.1021/acs.bioconjchem.7b00178

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