Enhancement of fluorescent properties of near-infrared dyes using clickable oligoglycerol dendrons

Orit Redy-Keisar, Katharina Huth, Uwe Vogel, Bernd Lepenies, Peter H. Seeberger, Rainer Haag, Doron Shabat

Research output: Contribution to journalArticlepeer-review

Abstract

Near-infrared (NIR) fluorescent dyes are gaining increased attention due to their potential to serve as molecular probes for in vivo imaging. Here, we demonstrate that oligoglycerol dendrons effectively enhance the fluorescence properties of an NIR dye by increasing the solubility in water and the prevention of aggregate formation. First- and second-generation oligoglycerol dendrons were conjugated to an NIR dye via a dipolar-cycloaddition (click) reaction. The two new dye conjugates exhibited enhanced NIR fluorescent emission and considerably higher fluorescent quantum yields than the dye alone. The high photostability measured for one of the oligoglycerol-linked dyes, in comparison to commonly used fluorogenic dyes such as Cy5 and Cy7, was validated using fluorescence microscopy of macrophages.

Original languageEnglish
Pages (from-to)4727-4732
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number16
DOIs
StatePublished - 28 Apr 2015

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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