title: Substituent Effects in BODIPY in Live Cell Imaging.
abstract: Small-molecule organoselenium-based fluorescent probes possess great capacity in understanding biological processes through the detection of various analytes such as reactive oxygen/nitrogen species (ROS/RNS), biothiols (cysteine, homocysteine and glutathione), lipid droplets, etc. Herein, we present how substituents on the BODIPY system play a significant part in the detection of biologically important analytes for in vitro conditions and live cell imaging studies. The fluorescence of the probe was quenched by 2-chloro and 6-phenyl selenium groups; the probe shows high selectivity with NaOCl among other ROS/RNS, and gives a turn-on response. The maximum fluorescence intensity is attained within ≈1-2 min with a low detection limit (19.6 nm), and shows a ≈110-fold fluorescence enhancement compared to signals generated for other ROS/RNS. Surprisingly, in live cell experiments, the probe specifically located and accumulated in lipid droplets, and showed a fluorescence turn-on response. We believe this turn-on response occurred because of aggregation-induced emission (AIE), which surprisingly occurred only by introducing one lipophilic mesityl group at the meso position of the BODIPY.
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: Molecular Logic Gate Laboratory, Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Republic of Korea.
authors.forename: Tesla
authors.initials: T
authors.lastname: Yudhistira
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: 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: Jinjoo
authors.initials: J
authors.lastname: Kim
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: 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.|Molecular Logic Gate Laboratory, Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 305-701, Republic of Korea.
authors.forename: David G
authors.initials: DG
authors.lastname: Churchill
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D005456:Fluorescent Dyes / Q000737:chemistry*; D006801:Humans; D008027:Light; D018613:Microscopy, Confocal; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D011789:Quantum Theory; D026361:Reactive Nitrogen Species / Q000737:chemistry; D017382:Reactive Oxygen Species / Q000737:chemistry; D012643:Selenium / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013234:Stem Cells / Q000166:cytology / Q000187:drug effects; D014466:Ultraviolet Rays
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D016566:Organoselenium Compounds; D026361:Reactive Nitrogen Species; D017382:Reactive Oxygen Species; D012643:Selenium
keywords: aggregation induced emission; bodipy; fluorescent probes; hypochlorous acid; lipids