A cascading reaction sequence involving ligand-directed azaelectrocyclization and autooxidation-induced fluorescence recovery enables visualization of target proteins on the surfaces of live cells

A general probe designed to induce a cascading sequence of reactions on a target protein was efficiently synthesized. The cascading reaction sequence involved (i) ligand-directed azaelectrocyclization with lysine and (ii) the autooxidation-induced release of a fluorescence quencher from the labeled...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-03, Vol.12 (9), p.1412-1418
Main Authors: Tanaka, Katsunori, Kitadani, Masataka, Tsutsui, Ayumi, Pradipta, Ambara R, Imamaki, Rie, Kitazume, Shinobu, Taniguchi, Naoyuki, Fukase, Koichi
Format: Article
Language:English
Subjects:
Animals
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Cell Line
Cell Survival
Cyclization
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Humans
Ligands
Mice
Models, Molecular
Molecular Structure
Oxidation-Reduction
Peptides, Cyclic - chemistry
Proteins - chemistry
Surface Properties
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Summary:A general probe designed to induce a cascading sequence of reactions on a target protein was efficiently synthesized. The cascading reaction sequence involved (i) ligand-directed azaelectrocyclization with lysine and (ii) the autooxidation-induced release of a fluorescence quencher from the labeled protein. The probe was linked to a cyclic RGDyK peptide to enable the selective visualization of integrin αVβ3 on the surfaces of live cells.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob42267d