席夫碱多功能金属离子探针的合成及在生物成像中的应用
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摘要
设计并合成了一个双席夫碱探针L,经~1H NMR、~(13)C NMR、HRMS(ESI-MS)及FT-IR等对其结构和组成进行了表征。紫外-可见光谱和荧光光谱研究结果表明,在无水乙醇-Tris-HCl缓冲液(9∶1,V/V,p H 7.40)中,探针L能同时对Ca~(2+)、Cu~(2+)和Zn~(2+)表现出较高的灵敏度和选择性。探针L对Cu~(2+)的检测,在335 nm处表现了显著的吸收强度增强;对Ca~(2+)和Zn~(2+)的检测,分别于515和486 nm处表现了特异的荧光增强。对Ca~(2+)、Cu~(2+)和Zn~(2+)的检出限分别为9.00×10!~7mol/L、9.23×10!~7mol/L和5.14×10!~7mol/L。将探针L应用于实际样品(药物、水样和血清)中Ca~(2+)、Cu~(2+)及Zn~(2+)检测,结果令人满意。探针L可用于Hep G2细胞、斑马鱼和活体小鼠中Ca~(2+)和Zn~(2+)的成像检测。
A novel probe L based on Schift base derivative was synthesized and characterized by1 H NMR,13 C NMR,HRMS and FT-IR spectroscopy. The interaction of this probe L with Ca~(2+),Cu~(2+)and Zn~(2+)was investigated by UV-Vis and fluorescence spectra systematically. The results showed that L exhibited high selectivity and sensitivity toward Ca~(2+),Cu~(2+)and Zn~(2+)ions over a wide range of metal ions and anions in ethanol and Tris-HCl( pH 7.4,9∶ 1,V/V) buffer solution. Meanwhile,L responded these three analytes with unique absorbance enhancement at 335 nm for Cu~(2+)and distinct fluorescent turned on signal changes at 512 nm and 486 for Ca~(2+)and Zn~(2+),respectively. The detection limits of L for Ca~(2+),Cu~(2+)and Zn~(2+)ions were 9.00×10~(-7) mol/L,9.23 × 10~(-7) mol/L and 5.14 × 10~(-7) mol/L,respectively. In additional,L was also successfully used to detect Ca~(2+),Cu~(2+)and Zn~(2+)in the samples( drug,water and serum samples) with satisfactory results.Notably,the L was successfully applied to imaging of Ca~(2+)and Zn~(2+)in HepG2 cells,zebra fish and living mice,which indicated that L had great potential in detection of Ca~(2+)and Zn~(2+)in vitro and in vivo.
A novel probe L based on Schift base derivative was synthesized and characterized by1 H NMR,13 C NMR,HRMS and FT-IR spectroscopy. The interaction of this probe L with Ca~(2+),Cu~(2+)and Zn~(2+)was investigated by UV-Vis and fluorescence spectra systematically. The results showed that L exhibited high selectivity and sensitivity toward Ca~(2+),Cu~(2+)and Zn~(2+)ions over a wide range of metal ions and anions in ethanol and Tris-HCl( pH 7.4,9∶ 1,V/V) buffer solution. Meanwhile,L responded these three analytes with unique absorbance enhancement at 335 nm for Cu~(2+)and distinct fluorescent turned on signal changes at 512 nm and 486 for Ca~(2+)and Zn~(2+),respectively. The detection limits of L for Ca~(2+),Cu~(2+)and Zn~(2+)ions were 9.00×10~(-7) mol/L,9.23 × 10~(-7) mol/L and 5.14 × 10~(-7) mol/L,respectively. In additional,L was also successfully used to detect Ca~(2+),Cu~(2+)and Zn~(2+)in the samples( drug,water and serum samples) with satisfactory results.Notably,the L was successfully applied to imaging of Ca~(2+)and Zn~(2+)in HepG2 cells,zebra fish and living mice,which indicated that L had great potential in detection of Ca~(2+)and Zn~(2+)in vitro and in vivo.
引文
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13 WANG Tao,MA La-Mao-Cao,MA Heng-Chang. Chinese J.Appl. Chem.,2018,35(10):1155-1165王涛,马拉毛草,马恒昌.应用化学,2018,35(10):1155-1165
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15 Tang L J,Ding S L,Yan X M. Inorg.Chem. Commun.,2016,74:35-38
16 XIE Di-Huan,SUN Chun,WANG Xiao-Jing,HAN Jie. Chem. J. Chinese Universities,2016,37(11):1966-1971谢迪欢,孙春,王晓静,韩杰.高等学校化学学报,2016,37(11):1966-1971
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18 Navneet K,Shweta C,Gagandeep S,Pushap R,Aman B,Suban K S,Anil K,Narinder S. J. Mater. Chem. B,2018,6:4872-4902
19 Yang J,Yuan Z L,Yu G Q,He S L,Wu Q,Hu Q H,Jiang B,Wei G. J. Fluoresc.,2016,26:43-51
20 Yu G Q,Cao Y P,Liu H M,Wu Q,Hu Q H,Jiang B,Yuan Z L. Sens. Actuators B,2017,245:803-814
2 MI Xiao-Long,JIAO Xiao-Jie,LIU Chang,HE Song,ZENG Xian-Shun. Chem. J. Chinese Universities,2016,37(10):1784-1791米小龙,焦晓洁,刘畅,何松,曾宪顺.高等学校化学学报,2016,37(10):1784-1791
3 Hung Y H,Bush A I,Cherny R A. J. Biol. Inorg.Chem.,2010,15(1):61-76
4 Wu J X,Yan B. Dalton. Trans.,2017,46(43):15080-15086
5 YANG An-Bo,XU Zhu-Xiong,WU Jing,FENG Yu-Ying,WANG Bing-Xiang. Chem. J. Chinese Universities,2010,31(7):1365-1368杨安博,徐助雄,吴婧,冯玉英,王炳祥.高等学校化学学报,2010,31(7):1365-1368
6 Frederickson C J,Koh J Y,Bush A I. Nat. Revi. Neurosci.,2005,6(6):449-462
7 Millett C E,Mukherjee D,Reider A,Can A,Maureen G,Dietmar F,Teodor T P,Shannon L K,Erika F H S. Psychiat.Res.,2017,255:52-58
8 WU Hong-Mei,GUO Yu,CAO Jian-Fang,WU Zhong-Li. Chin. J. Lumin.,2018,38(5):621-626吴红梅,郭宇,曹建芳,吴中立.发光学报,2018,38(5):621-626
9 Habte G,Hwang I M,Kim J S,Hong J H,Hong Y S,Choi J Y,Nho E Y,Jamila N,Khan N,Kim K S. Food Chem.,2016,212:512-520
10 Burford N,Eelman D M,Mahony D E,Morash M. Chem. Commun.,2003,9(1):146-147
11 MI Hong-Yu,GUAN Ming-Ming,HUAN Yan-Fu,FEI Qiang,ZHANG Zhi-Quan,FENG Guo-Dong. Chem. J. Chinese Universities,2017,38(12):2163-2168米红玉,关明明,郇延富,费强,张志权,冯国栋.高等学校化学学报,2017,38(12):2163-2168
12 YU Guang-Qin,YUAN Ze-Li,YANG Jie,WU Qing,HU Qing-Hong,ZHANG Ming-Qin,JIANG Bo,WEI Gang. Chinese J. Anal. Chem.,2016,44(10):1495-1503余光勤,袁泽利,杨洁,吴庆,胡庆红,张铭钦,江波,卫钢.分析化学,2016,44(10):1495-1503
13 WANG Tao,MA La-Mao-Cao,MA Heng-Chang. Chinese J.Appl. Chem.,2018,35(10):1155-1165王涛,马拉毛草,马恒昌.应用化学,2018,35(10):1155-1165
14 Maria L G,Giuseppe T S,Cristina S,Stefania Z,Gaetano A T,Agata C,Enrico R. Inorg. Chem.,2018,57(5):2365-2373
15 Tang L J,Ding S L,Yan X M. Inorg.Chem. Commun.,2016,74:35-38
16 XIE Di-Huan,SUN Chun,WANG Xiao-Jing,HAN Jie. Chem. J. Chinese Universities,2016,37(11):1966-1971谢迪欢,孙春,王晓静,韩杰.高等学校化学学报,2016,37(11):1966-1971
17 DU Zai-Hui,LI Xiang-Yang,TIAN Jing-jing,ZHANG Yang-Zi,TIAN Hong-Tao,XU Wen-Tao. Chinese J. Anal. Chem.,2018,46(7):995-1004杜再慧,李相阳,田晶晶,张洋子,田洪涛,许文涛.分析化学,2018,46(7):995-1004
18 Navneet K,Shweta C,Gagandeep S,Pushap R,Aman B,Suban K S,Anil K,Narinder S. J. Mater. Chem. B,2018,6:4872-4902
19 Yang J,Yuan Z L,Yu G Q,He S L,Wu Q,Hu Q H,Jiang B,Wei G. J. Fluoresc.,2016,26:43-51
20 Yu G Q,Cao Y P,Liu H M,Wu Q,Hu Q H,Jiang B,Yuan Z L. Sens. Actuators B,2017,245:803-814