title: Novel B,O-chelated fluorescent probe for nitric oxide imaging in Raw 264.7 macrophages and onion tissues.
abstract: A novel fluorescent probe based on B,O-chelated dipyrromethene chromophore in far-visible and near-infrared spectral region (600-900 nm), boron chelated 8-(3,4-diaminophenyl)-3,5-bis(2-hydroxyphenyl)-4-bora-3a,4a-diaza-s-indancene (BOPB), has been first developed for nitric oxide (NO) imaging. BOPB, a turn-on fluorescent probe, can react with NO rapidly under physiological condition. The reaction product of BOPB with NO, BOPB-T, emits bright red fluorescence at 643 nm when excited at 622 nm. Meanwhile, BOPB-T displays high fluorescent quantum yield of 0.21 and good photostability. The selectivity for NO over other reactive oxygen/nitrogen species and ascorbic acid has been investigated and BOPB has good specificity for the detection of NO. MTT assay shows that the toxicity of BOPB (below 10 μM) to living cells can be neglected. Based on these investigations, BOPB has been used for NO imaging in Raw 264.7 cells and onion tissues. Meanwhile, mechanical injury to onion tissues results in a brighter fluorescence around the wound, which indicates that more NO has been produced in plant tissues in response to external stimuli. Our studies illustrate that BOPB has advantages of high sensitivity, low background interference and little photo damage on fluorescence imaging of NO.
authors.affiliation: Key Laboratory of Analytical Chemistry for Biology and Medicine (Ministry of Education), Department of Chemistry, Wuhan University, Wuhan 430072, China.
authors.forename: Jian-Bo
authors.initials: JB
authors.lastname: Chen
authors.forename: Hui-Xian
authors.initials: HX
authors.lastname: Zhang
authors.forename: Xiao-Feng
authors.initials: XF
authors.lastname: Guo
authors.forename: Hong
authors.initials: H
authors.lastname: Wang
authors.forename: Hua-Shan
authors.initials: HS
authors.lastname: Zhang
mesh_terms: D000818:Animals; D001895:Boron / Q000737:chemistry; D002460:Cell Line; D002614:Chelating Agents / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D008264:Macrophages / Q000737:chemistry / Q000378:metabolism; D051379:Mice; D018613:Microscopy, Confocal; D009569:Nitric Oxide / Q000032:analysis*; D019697:Onions / Q000737:chemistry* / Q000378:metabolism; D010100:Oxygen / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry
chemical_list: D002614:Chelating Agents; D005456:Fluorescent Dyes; D011758:Pyrroles; C512015:dipyrromethane; D009569:Nitric Oxide; D001895:Boron; D010100:Oxygen
keywords: Boron chelated 8-(3,4-diaminophenyl)-3,5-bis(2-hydroxyphenyl)-4-bora-3a,4a-diaza-s-indancene; Fluorescence imaging; Nitric oxide; Onion tissues; Red-emitting