A Thiol-Reactive Fluorescence Probe Based on Donor-Excited Photoinduced Electron Transfer: Key Role of Ortho Substitution

We designed and synthesized a novel thiol-reactive fluorescence probe based on the BODIPY fluorophore. The fluorescence of this probe is strongly quenched by donor-excited photoinduced electron transfer (d-PeT) from BODIPY to maleimide, but after reaction with thiol, the fluorescence of BODIPY is re...

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Veröffentlicht in:	Organic letters 2007-08, Vol.9 (17), p.3375-3377
Hauptverfasser:	Matsumoto, Takuya, Urano, Yasuteru, Shoda, Takuji, Kojima, Hirotatsu, Nagano, Tetsuo
Format:	Artikel
Sprache:	eng
Schlagworte:	Boron Compounds - chemistry Electrons Fluorescent Dyes - chemistry Maleimides - chemistry Molecular Probes - chemical synthesis Sulfhydryl Compounds - analysis
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Beschreibung
Zusammenfassung:	We designed and synthesized a novel thiol-reactive fluorescence probe based on the BODIPY fluorophore. The fluorescence of this probe is strongly quenched by donor-excited photoinduced electron transfer (d-PeT) from BODIPY to maleimide, but after reaction with thiol, the fluorescence of BODIPY is restored, affording a 350-fold intensity increase.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol071352e