title: Novel pyrazoline-based fluorescent probe for detecting thiols and its application in cells.
abstract: A new compound, N-(4-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl)-acrylamide (probe L), was designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting thiol from other amino acids. On being mixed with thiol in buffered DMSO:HEPES=1:1 solution at pH 7.4, the probe exhibited the blue emission at 474 nm. This probe is very sensitive and displayed a linear fluorescence off-on response to thiol. The fluorescence emission of the probe is pH independent in the physiological pH range. Living cell imaging of HeLa cells confirmed its cell permeability and its ability to selectively detect thiol in cells. The structure of the probe was characterized by IR, NMR and HRMS spectroscopy analysis.
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Rong-Rong
authors.initials: RR
authors.lastname: Zhang
authors.affiliation: Institute of Developmental Biology, School of Life Science, Shandong University, Jinan 250100, PR China.
authors.forename: Jin-Feng
authors.initials: JF
authors.lastname: Zhang
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China; Linyi City Engineering Consulting Institute, Shandong University, Linyi 276015, PR China.
authors.forename: Sheng-Qing
authors.initials: SQ
authors.lastname: Wang
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Yan-Long
authors.initials: YL
authors.lastname: Cheng
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: D000178:Acrylamides / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D002021:Buffers; D060326:Chemistry Techniques, Synthetic; D003545:Cysteine / Q000737:chemistry; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D006531:HEPES / Q000737:chemistry; D006367:HeLa Cells / Q000187:drug effects; D006801:Humans; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D018613:Microscopy, Confocal; D008967:Molecular Biology / Q000379:methods*; D015394:Molecular Structure; D010539:Permeability; D011720:Pyrazoles / Q000737:chemistry; D012680:Sensitivity and Specificity; D013050:Spectrometry, Fluorescence; D013055:Spectrophotometry, Infrared; D013438:Sulfhydryl Compounds / Q000032:analysis* / Q000737:chemistry
chemical_list: D000178:Acrylamides; D000814:Aniline Compounds; D002021:Buffers; D005456:Fluorescent Dyes; C000601429:N-(4-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl)acrylamide; D011720:Pyrazoles; D013438:Sulfhydryl Compounds; C031280:pyrazole; D003545:Cysteine; D006531:HEPES; D004121:Dimethyl Sulfoxide
keywords: Fluorescent probe; Pyrazoline; Selective; Thiol