Premium
Enhanced Fluorescence Turn‐on Imaging of Hypochlorous Acid in Living Immune and Cancer Cells
Author(s) -
Mulay Sandip V.,
Choi Minsuk,
Jang Yoon Jeong,
Kim Youngsam,
Jon Sangyong,
Churchill David G.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601270
Subject(s) - hypochlorous acid , fluorescence , chemistry , reactive oxygen species , bodipy , photochemistry , fluorescence lifetime imaging microscopy , confocal , turn (biochemistry) , biophysics , biochemistry , biology , optics , physics
Abstract Two closely related phenyl selenyl based boron‐dipyrromethene (BODIPY) turn‐on fluorescent probes for the detection of hypochlorous acid (HOCl) were synthesized for studies in chemical biology; emission intensity is modulated by a photoinduced electron‐transfer (PET) process. Probe 2 intrinsically shows a negligible background signal; however, after reaction with HOCl, chemical oxidation of selenium forecloses the PET process, which evokes a significant increase in fluorescence intensity. The fluorescence intensity of probes 1 and 2 with HOCl involves an ∼18 and ∼50‐fold enhancement compared with the respective responses from other reactive oxygen/nitrogen species (ROS/RNS) and low detection limits (30.9 n m for 1 and 4.5 n m for 2 ). Both probes show a very fast response with HOCl; emission intensity reached a maximum within 1 s. These probes show high selectivity for HOCl, as confirmed by confocal microscopy imaging when testing with RAW264.7 and MCF‐7 cells.