New repertoire of 'donor-two-acceptor' NIR fluorogenic dyes

Einat Kisin-Finfer, Doron Shabat

Research output: Contribution to journalArticlepeer-review

Abstract

Dye molecules with various fluorescent wavelengths are widely used for diagnostic and optical imaging applications. Accordingly, there is a constant demand for fluorogenic dyes with new properties. We have recently developed a novel strategy for the design of long-wavelength fluorescent dyes with a turn-ON option. The design is based on a donor-two-acceptor π-electron system that can undergo an internal charge transfer to form a new fluorochrome with an extended π-conjugated system. Here, we describe a series of such dyes based on two novel latent donors, naphthol and hydroxycoumarin. One of the dyes has showed excellent near-infrared fluorescent characteristics and specifically was demonstrated as a mitochondrial imaging reagent in live cells. This unique strategy for fluorogenic dye design has opened new doors for further near-infrared fluorescence probe discovery.

Original languageEnglish
Pages (from-to)3602-3608
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume21
Issue number12
DOIs
StatePublished - 15 Jun 2013

Keywords

  • Fluorescence assay
  • NIR fluorescence
  • Turn-ON probes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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