Clickable fluorophores for biological labeling--with or without copper.
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.
Kele
Péter
P
Institute of Chemistry, Eötvös Loránd University, H-1117, Pázmány Péter sétány 1a, Budapest, Hungary. kelep@elte.hu
Li
Xiaohua
X
Link
Martin
M
Nagy
Krisztina
K
Herner
András
A
Lorincz
Krisztián
K
Béni
Szabolcs
S
Wolfbeis
Otto S
OS
D000818:Animals; D016466:CHO Cells; D003300:Copper / Q000737:chemistry*; D006224:Cricetinae; D003412:Cricetulus; D034242:Cyclooctanes / Q000737:chemistry; D003516:Cycloparaffins / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D015336:Molecular Probe Techniques; D011134:Polysaccharides / Q000737:chemistry
D034242:Cyclooctanes; D003516:Cycloparaffins; D005456:Fluorescent Dyes; D011134:Polysaccharides; D003300:Copper; C474479:cyclooctane