Enhanced Fluorescence Turn‐on Imaging of Hypochlorous Acid in Living Immune and Cancer Cells. Issue 28 (31st May 2016)

• Record Type: Journal Article
• Authors: Mulay, Sandip V.; Choi, Minsuk; Jang, Yoon Jeong; Kim, Youngsam; Jon, Sangyong; Churchill, David G.
• Is Part Of: Chemistry. Volume 22:Issue 28(2016)
• Page Start: 9642
• Page End: 9648
• Publication Date: 2016-05-31
• Subjects: biosensing -- BODIPY -- fluorescence -- hypochlorous acid -- photoinduced electron transfer; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201601270
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Probe2 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 probes1 and2 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 nm for1 and 4.5 nm for2 ). 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. Abstract : Organoselenium HOCI detectors : Two organoselenium‐based boron‐dipyrromethene (BODIPY) turn‐on fluorescent probes for selective and sensitive detection of hypochlorous acid over other reactive oxygen/nitrogen species (ROS/RNS) were reported. The emission intensity of these probes was modulated by a photoinduced electron‐transfer (PET) process (see figure).