title: Reaction-based epoxide fluorescent probe for in vivo visualization of hydrogen sulfide.
abstract: Hydrogen sulfide (H2S) has emerged as the most important biosynthetic gasotransmitters along with nitric oxide (NO) and carbon monoxide (CO). In this study, we report the design and the synthesis of a new epoxide fluorescent probe 7-glycidyloxy-9-(2-glycidyloxycarbonylphenyl)-2-xanthone (FEPO) for use in in vivo visualization of hydrogen sulfide. The probe employs a fluorescein as a fluorophore, and is equipped with an operating epoxide unit. FEPO functions via epoxide ring opening upon nucleophilic attack of H2S. This ring opening strategy may open a new avenue for the development of various H2S fluorescent sensors. FEPO showed high selectivity and high sensitivity for H2S. FEPO's cytotoxicity was tested using MTT (2-(4,5-dimethyl-2-thiazolyl)-3,5-diphenyl-2H-tetrazolium bromide) assay. Furthermore, the use of confocal imaging of H2S and in vivo imaging in live zebra fish demonstrated FEPO's potential biological applications. We anticipate that, owing to their ideal properties, probes of this type will find great uses in exploring the role of H2S in biology.
authors: Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
authors: Palanisamy
authors: P
authors: Sathyadevi
authors: Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
authors: Yu-Jen
authors: YJ
authors: Chen
authors: Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
authors: Shou-Cheng
authors: SC
authors: Wu
authors: Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
authors: Yen-Hao
authors: YH
authors: Chen
authors: Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan; Department of Biomedical Science and Environmental Biology, Kaohsiung Medical University, Kaohsiung 807, Taiwan. Electronic address: ymwang@mail.nctu.edu.tw.
authors: Yun-Ming
authors: YM
authors: Wang
mesh_terms: D015374:Biosensing Techniques; D004852:Epoxy Compounds / Q000737:chemistry; D005456:Fluorescent Dyes; D006862:Hydrogen Sulfide / Q000737:chemistry / Q000302:isolation & purification*; D018613:Microscopy, Confocal
chemical_list: D004852:Epoxy Compounds; D005456:Fluorescent Dyes; D006862:Hydrogen Sulfide
keywords: Confocal imaging; Fluorescein; H(2)S detection; Zebra fish