NIR mega-stokes fluorophores for bioorthogonal labeling and energy transfer systems - An efficient quencher for daunomycin

Gergely B. Cserép, Kata N. Enyedi, Attila Demeter, Gábor Mezo, Péter Kele

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A set of new azide- and alkyne-bearing lepidinium-based fluorophores were synthesized for bioorthogonal labeling schemes. These fluorescent dyes all show large Stokes-shifts with emission maxima in the near-infrared (NIR) region of the electromagnetic spectrum. The applicability of these dyes in the construction of energy-transfer systems was tested using one of these new fluorescent tags and daunomycin (Dau), an anticancer drug with fluorescent features. These daunomycin conjugates are the very first examples of fluorescently modulated constructs of this anticancer agent. The dually labeled architectures proved that the applied fluorescent dye can be utilized as an efficient quencher for daunomycin. Enzymatic cleavage of a dually labeled enzyme substrate resulted in full recovery of the fluorescence of daunomycin. Such fluorescently modulated Dau conjugates can provide useful information for the mechanism of action of Dau-regulated cell death processes.

Original languageEnglish
Pages (from-to)494-502
Number of pages9
JournalChemistry - An Asian Journal
Volume8
Issue number2
DOIs
Publication statusPublished - Feb 1 2013

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Keywords

  • FRET
  • bioorthogonal
  • daunomycin
  • fluorescent probes
  • quenching

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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