5-苯基-2-邻甲苯-2H-1,2,3-三氮唑-4-羧酸乙酯的结构性质及其罗丹明衍生物检测汞离子  

Structural Properties of Ethyl 5-Phenyl-2-(o-tolyl)-2H-1,2,3-triazole-4-carboxylate and Its Appended Rhodamine for Detection of Hg^2+

作　　者：何文英[1] 廖元淏 丁国华 李建玲 刘炜[1] 刘艳萍[1] 冯华杰[1] HE Wen-ying;LIAO Yuan-hao;DING Guo-hua;LI Jian-ling;LIU Wei;LIU Yan-ping;FENG Hua-jie(Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education,Hainan Normal University,Haikou 571158,China;College of Life and Sciences,Hainan Normal University,Haikou 571158,China)

机构地区：[1]海南师范大学热带药用植物化学教育部重点实验室,海南海口571158 [2]海南师范大学生命科学学院,海南海口571158

出　　处：《化学试剂》2020年第5期483-492,共10页Chemical Reagents

基　　金：国家自然科学基金资助项目(21562019);海南省自然科学基金资助项目(219MS040);海南省自然科学基金创新研究团队项目(2016CXTD007)。

摘　　要：应用计算化学的方法研究了5-苯基-2-邻甲苯-2H-1,2,3-三氮唑-4-羧酸乙酯(EPTC)的结构及理论光谱,并与实验测定结果相比较;再将EPTC与罗丹明B合成了新化合物REPTC,采用紫外吸收和荧光光谱法测定了REPTC与16种金属离子的相互作用。实验结果表明:在pH 7.4的N,N-二甲基甲酰胺(DMF)-水溶液中,REPTC在2.33×10^-5~4.00×10^-5 mol/L的浓度范围内,仅对Hg^2+有高选择性的响应,表现为在577 nm处出现一个新的发射峰且强度显著增大,同时肉眼可观察到明显的颜色变化。结合电喷雾质谱及理论计算表明:Hg^2+的存在使得REPTC分子中罗丹明的螺环结构从闭环转为开环,可与Hg^2+形成物质的量比为1∶2的新配合物。荧光成像实验表明:REPTC可成功标记HeLa细胞中的Hg2+,进而可开发用于生物体系中Hg^2+的测定。A newly synthesized compound———ethyl 5-phenyl-2-(o-tolyl)-2H-1,2,3-triazole-4-carboxylate(EPTC)has been used to investigate its structural properties and theoretical spectrum which is consistent with the experimental spectrum.Then EPTC was successfully designed and synthesized to a new rhodamine B derivative REPTC confirmed by 1HNMR,13CNMR,and HRMS.The spectral sensing behaviors of REPTC toward 16 kinds of metal ions were determined by fluorescence spectra and UV absorption spectra.The probe REPTC showed high selectivity toward Hg^2+ions in DMF-H2O between a range of REPTC concentration 2.33×10^-5~4.00×10^-5 mol/L under physiological conditions(pH 7.4).A new emission peak appeared at 577 nm and enhanced significantly along with naked-eye sensitive color changes,which spirolactamring moiety of rhodamine was converted to the open-ring form in the presence of Hg^2+and formed the new complex as 1∶2 material ratio.The fluorescence imaging results of Hg^2+in HeLa cell demonstrated that the probe was successfully labeled and it could be further exploited and used in biological systems.

关 键 词：5-苯基-2-邻甲苯-2H-1 2 3-三氮唑-4-羧酸乙酯 结构性质 合成 Hg^2+离子 细胞成像 

分 类 号：O657[理学—分析化学]