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Bioconjug Chem. 2008 Dec;19(12):2487-91. doi: 10.1021/bc800417b.

Monofunctional carbocyanine dyes for bio- and bioorthogonal conjugation.

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  • 1Center for Molecular Imaging Research and Center for Systems Biology, Massachusetts General Hospital/Havard Medical School, Room 5404, Building 149, 13th Street, Charlestown, Massachusetts 02129, USA.


A facile synthetic route to prepare monofunctional carbocyanine dyes for biological application is developed. Three pentamethine carbocyanine dyes have been successfully modified with a variety of functional groups such as: carboxylic acids, azides, or alkynes. The new dyes are characterized by strong NIR fluorescence emission, high extinction coefficients and good quantum yields. The azide and alkyne dyes have potential utility as components in bioorthogonal labeling schemes via [2 + 3] dipolar cycloaddition "click" reactions. The application of one derivative, CyAM-5 alkyne, for bioorthogonal labeling is demonstrated. Fluorescence microscopy shows coupling of CyAM-5 alkyne to Chinese hamster ovary (CHO) cells preincubated with azide modified glycans.

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