title: Enhanced Fluorescence Turn-on Imaging of Hypochlorous Acid in Living Immune and Cancer Cells.
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 nm for 1 and 4.5 nm 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.
authors.affiliation: Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, 305-701, Republic of Korea.|Molecular Logic Gate Laboratory, Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Republic of Korea.
authors.forename: Sandip V
authors.initials: SV
authors.lastname: Mulay
authors.affiliation: Department of Biological Sciences, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Republic of Korea.
authors.forename: Minsuk
authors.initials: M
authors.lastname: Choi
authors.affiliation: Molecular Logic Gate Laboratory, Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Republic of Korea.
authors.forename: Yoon Jeong
authors.initials: YJ
authors.lastname: Jang
authors.affiliation: Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, 305-701, Republic of Korea.|Molecular Logic Gate Laboratory, Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Republic of Korea.
authors.forename: Youngsam
authors.initials: Y
authors.lastname: Kim
authors.affiliation: Department of Biological Sciences, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Republic of Korea.
authors.forename: Sangyong
authors.initials: S
authors.lastname: Jon
authors.affiliation: Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, 305-701, Republic of Korea. dchurchill@kaist.ac.kr.|Molecular Logic Gate Laboratory, Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Republic of Korea. dchurchill@kaist.ac.kr.
authors.forename: David G
authors.initials: DG
authors.lastname: Churchill
mesh_terms: D001895:Boron; D002460:Cell Line; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D006801:Humans; D006997:Hypochlorous Acid / Q000737:chemistry*; D057230:Limit of Detection; D061986:MCF-7 Cells; D018613:Microscopy, Confocal / Q000379:methods*; D010084:Oxidation-Reduction; D011162:Porphobilinogen / Q000031:analogs & derivatives* / Q000737:chemistry; D012643:Selenium / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; C507544:dipyrromethene; D006997:Hypochlorous Acid; D011162:Porphobilinogen; D012643:Selenium; D001895:Boron
keywords: BODIPY; biosensing; fluorescence; hypochlorous acid; photoinduced electron transfer