title: NIR mega-Stokes fluorophores for bioorthogonal labeling and energy transfer systems--an efficient quencher for daunomycin.
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.
authors.affiliation: Institute of Chemistry, Eötvös Loránd University, H-1117, Pázmány Péter sétány 1a, Budapest, Hungary.
authors.forename: Gergely B
authors.initials: GB
authors.lastname: Cserép
authors.forename: Kata N
authors.initials: KN
authors.lastname: Enyedi
authors.forename: Attila
authors.initials: A
authors.lastname: Demeter
authors.forename: Gábor
authors.initials: G
authors.lastname: Mező
authors.forename: Péter
authors.initials: P
authors.lastname: Kele
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D061565:Cycloaddition Reaction; D003630:Daunorubicin / Q000737:chemistry*; D031541:Fluorescence Resonance Energy Transfer; D005456:Fluorescent Dyes / Q000737:chemistry*; D019265:Spectroscopy, Near-Infrared
chemical_list: D000480:Alkynes; D001386:Azides; D005456:Fluorescent Dyes; D003630:Daunorubicin