title: Novel pyrazoline-based fluorescent probe for detecting glutathione and its application in cells.
abstract: A novel compound, 2-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl acrylate (probe L), was designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting glutathione among cysteine, homocysteine and other amino acids. The structures of related compounds were characterized using IR, NMR and HRMS spectroscopy analysis. The probe is a non-fluorescent compound. On being mixed with glutathione in buffered EtOH:PBS=3:7 solution at pH 7.4, the probe exhibited the blue emission of the pyrazoline at 474 nm and a 83-fold enhancement in fluorescence intensity. This probe is very sensitive and displayed a linear fluorescence off-on response to glutathione with fluorometric detection limit of 8.2 × 10(-8)M. The emission of the probe is pH independent in the physiological pH range. Live-cell imaging of HeLa cells confirmed the cell permeability of the probe and its ability to selectively discriminate GSH from Cys and Hcy in cells. The toxicity of the probe was low in cultured HeLa cells.
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Sheng-Qing
authors.initials: SQ
authors.lastname: Wang
authors.affiliation: Institute of Developmental Biology, School of Life Science, Shandong University, Jinan 250100, PR China.
authors.forename: Qing-Hua
authors.initials: QH
authors.lastname: Wu
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Hao-Yan
authors.initials: HY
authors.lastname: Wang
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Xiao-Xin
authors.initials: XX
authors.lastname: Zheng
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Shi-Li
authors.initials: SL
authors.lastname: Shen
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Yan-Ru
authors.initials: YR
authors.lastname: Zhang
authors.affiliation: Institute of Developmental Biology, School of Life Science, Shandong University, Jinan 250100, PR China. Electronic address: miaojy@sdu.edu.cn.
authors.forename: Jun-Ying
authors.initials: JY
authors.lastname: Miao
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China. Electronic address: bxzhao@sdu.edu.cn.
authors.forename: Bao-Xiang
authors.initials: BX
authors.lastname: Zhao
mesh_terms: D002470:Cell Survival / Q000187:drug effects; D005456:Fluorescent Dyes / Q000032:analysis / Q000138:chemical synthesis* / Q000633:toxicity; D005978:Glutathione / Q000378:metabolism*; D006367:HeLa Cells; D006801:Humans; D015336:Molecular Probe Techniques; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000633:toxicity; D013050:Spectrometry, Fluorescence / Q000379:methods*; D013347:Subcellular Fractions / Q000187:drug effects / Q000378:metabolism*
chemical_list: D005456:Fluorescent Dyes; D011720:Pyrazoles; D005978:Glutathione
keywords: Fluorescent sensor; Glutathione; Pyrazoline; Selective