"donor-two-acceptor" dye design: A distinct gateway to NIR fluorescence

Naama Karton-Lifshin, Lorenzo Albertazzi, Michael Bendikov, Phil S. Baran, Doron Shabat

Research output: Contribution to journalArticle

120 Citations (Scopus)

Abstract

The detection of chemical or biological analytes upon molecular reactions relies increasingly on fluorescence methods, and there is a demand for more sensitive, more specific, and more versatile fluorescent molecules. We have designed long wavelength fluorogenic probes with a turn-ON mechanism based on a donor-two-acceptor π-electron system that can undergo an internal charge transfer to form new fluorochromes with longer π-electron systems. Several latent donors and multiple acceptor molecules were incorporated into the probe modular structure to generate versatile dye compounds. This new library of dyes had fluorescence emission in the near-infrared (NIR) region. Computational studies reproduced the observed experimental trends well and suggest factors responsible for high fluorescence of the donor-two-acceptor active form and the low fluorescence observed from the latent form. Confocal images of HeLa cells indicate a lysosomal penetration pathway of a selected dye. The ability of these dyes to emit NIR fluorescence through a turn-ON activation mechanism makes them promising candidate probes for in vivo imaging applications.

Original languageEnglish
Pages (from-to)20412-20420
Number of pages9
JournalJournal of the American Chemical Society
Volume134
Issue number50
DOIs
Publication statusPublished - Dec 19 2012

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Coloring Agents
Dyes
Fluorescence
Infrared radiation
Electrons
Molecules
Fluorescent Dyes
HeLa Cells
Charge transfer
Chemical activation
Imaging techniques
Wavelength

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

"donor-two-acceptor" dye design : A distinct gateway to NIR fluorescence. / Karton-Lifshin, Naama; Albertazzi, Lorenzo; Bendikov, Michael; Baran, Phil S.; Shabat, Doron.

In: Journal of the American Chemical Society, Vol. 134, No. 50, 19.12.2012, p. 20412-20420.

Research output: Contribution to journalArticle

Karton-Lifshin, Naama ; Albertazzi, Lorenzo ; Bendikov, Michael ; Baran, Phil S. ; Shabat, Doron. / "donor-two-acceptor" dye design : A distinct gateway to NIR fluorescence. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 50. pp. 20412-20420.
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