Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 13, Pages 3619-3629Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201002268
Keywords
CuAAC; cycloaddition; dendrimers; dendrons; dyes/pigments; imaging agent; SPAAC
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Funding
- New York University
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Cyanine dyes are known for their fluorescence in the near-IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct S(NR)1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging.
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