title: Nitric oxide turn-on fluorescent probe based on deamination of aromatic primary monoamines.
abstract: The stable, water-soluble, and nonfluorescent FA-OMe can sense nitric oxide (NO) and form the intensely fluorescent product dA-FA-OMe via reductive deamination of the aromatic primary amine. The reaction is accompanied by a notable increase of the fluorescent quantum yield from 1.5 to 88.8%. The deamination mechanism of FA-OMe with NO was proposed in this study. The turn-on fluorescence signals were performed by suppression of photoinduced electron transfer (PeT), which was demonstrated by density functional theory (DFT) calculations of the components forming FA-OMe and dA-FA-OMe. Furthermore, FA-OMe showed water solubility and good stability at physiological pHs. Moreover, the selectivity study indicated that FA-OMe had high specificity for NO over other reactive oxygen/nitrogen species. In an endogenously generated NO detection study, increasing the incubation time of FA-OMe with lipopolysaccharide (LPS) pretreated Raw 264.7 murine macrophages could cause an enhanced fluorescence intensity image. In addition, a diffusion/localization cell imaging study showed that FA-OMe could be trapped in Raw 264.7 cells. These cell imaging results demonstrated that FA-OMe could be used as a turn-on fluorescent sensor for the detection of endogenously generated NO.
authors.affiliation: Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
authors.forename: Tsun-Wei
authors.initials: TW
authors.lastname: Shiue
authors.forename: Yen-Hao
authors.initials: YH
authors.lastname: Chen
authors.forename: Chi-Ming
authors.initials: CM
authors.lastname: Wu
authors.forename: Gyan
authors.initials: G
authors.lastname: Singh
authors.forename: Hsing-Yin
authors.initials: HY
authors.lastname: Chen
authors.forename: Chen-Hsiung
authors.initials: CH
authors.lastname: Hung
authors.forename: Wen-Feng
authors.initials: WF
authors.lastname: Liaw
authors.forename: Yun-Ming
authors.initials: YM
authors.lastname: Wang
mesh_terms: D000586:Amination; D000588:Amines / Q000737:chemistry*; D000818:Animals; D002460:Cell Line; D002470:Cell Survival; D004579:Electron Transport; D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D051379:Mice; D057054:Molecular Imaging; D009569:Nitric Oxide / Q000737:chemistry* / Q000378:metabolism; D055668:Photochemical Processes; D011789:Quantum Theory
chemical_list: D000588:Amines; D005456:Fluorescent Dyes; D009569:Nitric Oxide