A thiol-reactive fluorescence probe based on donor-excited photoinduced electron transfer: key role of ortho substitution

  • Org Lett. 2007 Aug 16;9(17):3375-7. doi: 10.1021/ol071352e.
Takuya Matsumoto  1 ,  Yasuteru Urano ,  Takuji Shoda ,  Hirotatsu Kojima ,  Tetsuo Nagano
Affiliations
  • 1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Tokyo 113-0033 Japan.
PMID: 17645349 DOI: 10.1021/ol071352e
Abstract

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.

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