Combining aminocyanine dyes with polyamide dendrons: A promising strategy for imaging in the near-infrared region

Cátia Ornelas, Rachelle Lodescar, Alexander Durandin, James W. Canary, Ryan Pennell, Leonard F. Liebes, Marcus Weck

Research output: Contribution to journalArticle

Abstract

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 SNR1 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.

Original languageEnglish (US)
Pages (from-to)3619-3629
Number of pages11
JournalChemistry - A European Journal
Volume17
Issue number13
DOIs
StatePublished - Mar 21 2011

Keywords

  • CuAAC
  • SPAAC
  • cycloaddition
  • dendrimers
  • dendrons
  • dyes/pigments
  • imaging agent

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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