title: A new turn-on fluorescence probe for Zn(2+) in aqueous solution and imaging application in living cells.
abstract: We designed and synthesized a new pyrazoline-based turn-on fluorescence probe for Zn(2+) by the reaction of chalcone and thiosemicarbazide. The structure of the probe was characterized by IR, NMR and HRMS spectroscopy. The probe (L) exhibits high selectivity and sensitivity for detecting Zn(2+) in buffered EtOH/HEPES solution (EtOH/HEPES=1/1, pH 7.2) with 80-fold fluorescence enhancement, which is superior to previous reports. Job's plot analysis revealed 1:1 stoichiometry between probe L and Zn(2+) ions. The association constant estimated by the Benesi-Hildebrand method and the detection limit were 3.92×10(3)M(-1) and 5.2×10(-7)M, respectively. A proposed binding mode was confirmed by (1)H NMR titration experiments and density functional theory (DFT) calculations. The probe is cell-permeable and stable at the physiological pH range in biological systems. Because of its fast response to Zn(2+), the probe can monitor Zn(2+) in living cells. Moreover, the selective binding of L and Zn(2+) was reversible with the addition of EDTA in buffered EtOH/HEPES solution and Zn(2+) could be imaged in SH-SY5Y neuron cells.
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Meng-Meng
authors.initials: MM
authors.lastname: Li
authors.affiliation: Institute of Developmental Biology, School of Life Science, Shandong University, Jinan 250100, PR China.
authors.forename: Fang-Wu
authors.initials: FW
authors.lastname: Wang
authors.affiliation: Chemical Technology Academy of Shandong Province, Jinan 250014, PR China.
authors.forename: Xiao-Yun
authors.initials: XY
authors.lastname: Wang
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Ting-Ting
authors.initials: TT
authors.lastname: Zhang
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Xu
authors.affiliation: Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Xiao
authors.affiliation: Institute of Developmental Biology, School of Life Science, Shandong University, Jinan 250100, PR China.
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: D045744:Cell Line, Tumor; D005456:Fluorescent Dyes / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D009474:Neurons / Q000737:chemistry*; D011720:Pyrazoles / Q000737:chemistry*; D013854:Thioamides / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
chemical_list: C000596871:3-(2-hydroxy-5-methylphenyl)-5-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carbothioamide; D005456:Fluorescent Dyes; D011720:Pyrazoles; D013854:Thioamides; D015032:Zinc
keywords: Fluorescent probe; Imaging; Neuron cells; Pyrazoline; Reversibility; Zinc ion