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Paper
Org. Biomol. Chem., 2009, 7, 3486 - 3490, DOI: 10.1039/b907741c
Clickable fluorophores for biological labeling—with or without copper
Péter Kele, Xiaohua Li, Martin Link, Krisztina Nagy, András Herner, Krisztián L
rincz, Szabolcs Béni and Otto S. Wolfbeis
The synthesis of a set of new clickable fluorophores that virtually cover the whole visible spectrum reaching the near infra-red regime is presented herein. Besides dyes that are capable of participating in classical copper catalyzed 1,3-dipolar cycloaddition reactions with the counterparting function we have also prepared dyes containing a cyclooctyne moiety, an alkyne derivative that enables copper free clicking to azides. The suitability of these dyes for fluorescent labeling of biomolecules is presented by examples on model frameworks representing major biopolymer building blocks. The versatility of these dyes is presented in cell labeling experiments as well as by labeling the azide modified surface glycans of CHO-cells either by copper catalyzed or copper-free click reaction. These dyes are expected to have a large variety of applications in (bio)orthogonal labeling schemes both in vivo and in vitro.
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