title: An Amphiphilic Fluorescent Probe Designed for Extracellular Visualization of Nitric Oxide Released from Living Cells.
abstract: Nitric oxide (NO) is an intracellular and intercellular messenger involved in numerous physiological and pathophysiological processes. Small-molecule fluorescent probes coupled with fluorescence microscopy provide excellent tools for real-time detection of NO in situ. However, most probes are designed for imaging intracellular NO, which cannot reflect the release behavior of endogenously produced NO. In order to visualize extracellular NO released from living cells, we report herein a particularly designed amphiphilic fluorescent probe, disodium 2,6-disulfonate-1,3-dimethyl-5-hexadecyl-8-(3,4-diaminophenyl)-4,4'-difluoro-4-bora-3a,4a-diaza-s-indacene (DSDMHDAB), in which hydrophilic groups are introduced to keep the fluorophore and recognition domain outside the cell and a hydrophobic C16 alkyl chain acts as the membrane anchor. Based on this design, NO released out of the cells has been visualized on the outer surface of the plasma membrane. Using RAW 264.7 cells and ECV-304 cells as models, the diffusion of NO across the plasma membrane has been directly observed. The amphiphilic design strategy of fluorescent probes holds great promise for developing fluorescent imaging probes to study the release behaviors of other endogenous gasotransmitters.
authors.affiliation: Key Laboratory of Analytical Chemistry for Biology and Medicine (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University , Wuhan 430072, China.
authors.forename: Hui-Wen
authors.initials: HW
authors.lastname: Yao
authors.affiliation: Key Laboratory of Analytical Chemistry for Biology and Medicine (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University , Wuhan 430072, China.
authors.forename: Xiao-Yan
authors.initials: XY
authors.lastname: Zhu
authors.affiliation: Key Laboratory of Analytical Chemistry for Biology and Medicine (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University , Wuhan 430072, China.
authors.forename: Xiao-Feng
authors.initials: XF
authors.lastname: Guo
authors.affiliation: Key Laboratory of Analytical Chemistry for Biology and Medicine (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University , Wuhan 430072, China.
authors.forename: Hong
authors.initials: H
authors.lastname: Wang
mesh_terms: D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D001880:Boranes / Q000737:chemistry*; D002460:Cell Line; D005456:Fluorescent Dyes / Q000737:chemistry*; D054879:Halogenation; D006801:Humans; D051379:Mice; D008856:Microscopy, Fluorescence / Q000379:methods*; D009569:Nitric Oxide / Q000032:analysis*; D061848:Optical Imaging / Q000379:methods*; D000067996:RAW 264.7 Cells; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D001880:Boranes; D005456:Fluorescent Dyes; D013501:Surface-Active Agents; C476083:boradiazaindacene; D009569:Nitric Oxide; D015082:2,2'-Dipyridyl