SIOC English
有机化学
高级检索

有机化学 >

2019 , Vol. 39 >Issue 12: 3498 - 3504

DOI: https://doi.org/10.6023/cjoc201906004

研究论文

一种“关-开”型生物硫醇荧光探针和生物成像应用

  • 周婷婷 ,
  • 杨瑜涛 ,
  • 周柯岩 ,
  • 胥稳智 ,
  • 李玮
展开
  • a 河北大学化学与环境科学学院 保定 071002;
    b 河北大学药物化学与分子诊断教育部重点实验室 保定 071002

收稿日期: 2019-06-05

  修回日期: 2019-07-06

  网络出版日期: 2019-08-01

基金资助

国家自然科学基金（No.21807021）、河北大学药物化学与分子诊断教育部重点实验室提升计划（No.ts2019004）、河北省自然科学青年基金（No.B2017201093）和河北大学高层次引进人才资助项目.

收起

An “Off-On” Fluorescent Probe for Biothiols and Its Application in Bioimaging

  • Zhou Tingting ,
  • Yang Yutao ,
  • Zhou Keyan ,
  • Xu Wenzhi ,
  • Li Wei
Expand
  • a College of Chemistry & Environmental Science, Hebei University, Baoding 071002;
    b Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Hebei University, Baoding 071002

Received date: 2019-06-05

  Revised date: 2019-07-06

  Online published: 2019-08-01

Supported by

Project supported by the National Natural Science Foundation of China (No. 21807021), the Priority Strategy Project of Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education (No. ts2019004), the Science Foundation for Youth of Hebei Province (No. B2017201093) and the Hebei University Science Foundation for High-Level Personnel.

Fold

摘要

设计合成了一种基于香豆素衍生物的“关-开”型荧光探针CO-NBS，用于选择性识别生物硫醇，包括半胱氨酸（Cys）、高半胱氨酸（Hcy）和谷胱甘肽（GSH）.采用紫外-可见吸收光谱和荧光光谱对该探针的光学性能进行研究，实验结果表明，该探针能够实现对Cys、Hcy和GSH快速、高灵敏性和高选择性的检测，检测限分别为92、30、62 nmol/L.此外，该探针具有低细胞毒性和良好的生物相容性，能够成功应用于活细胞和斑马鱼中的生物硫醇的荧光成像.

关键词： 荧光探针; 香豆素衍生物; 生物硫醇; 荧光成像

本文引用格式

周婷婷 , 杨瑜涛 , 周柯岩 , 胥稳智 , 李玮 . 一种“关-开”型生物硫醇荧光探针和生物成像应用[J]. 有机化学, 2019 , 39(12) : 3498 -3504 . DOI: 10.6023/cjoc201906004

Abstract

An "off-on" fluorescent probe CO-NBS based coumarin derivative was designed and synthesized, which can respond selectively with biothiols including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH). The optical properties were studied by UV-Vis absorption spectrum and fluorescence spectrum. The results showed that probe was capable to respond rapidly, sensitively and selectively to Cys, Hcy and GSH with the detection limits of 92, 30 and 62 nmol/L, respectively. In addition, with low cytotoxicity and good biocompatibility, the probe can be successfully applied to image biothiols in living cells and in living zebrafish.

Key words： fluorescent probe; coumarin derivatives; biothiols; fluorescence imaging

参考文献

[1] Zhang, S.; Ong, C. N.; Shen, H. M. Cancer Lett. 2004, 208, 143.
[2] Wang, S. Q.; Shen, S. L.; Zhang, Y. R.; Dai, X.; Zhao, B. X. Chin. J. Org. Chem. 2014, 34, 1717(in Chinese). (王胜清, 申世立, 张延如, 戴溪, 赵宝祥, 有机化学, 2014, 34, 1717.)
[3] Yan, P. P.; Wang. T.; Zhang. D.; Ma, X. Y. Chin. J. Org. Chem. 2019, 39, 916(in Chinese). (闫沛沛, 王婷, 张丹, 马晓雪, 有机化学, 2019, 39, 916.)
[4] Niu, L. Y.; Chen, Y. Z.; Zheng, H. R.; Wu, L. Z.; Tung, C. H.; Yang, Q. Z. Chem. Soc. Rev. 2015, 44, 6143.
[5] Weerapana, E.; Wang, C.; Simon, G. M.; Richter, F.; Khare, S.; Dillon, M. B. D.; Bachovchin, D. A.; Mowen, K.; Baker, D. Nature 2010, 468, 790.
[6] Yue, Y. K.; Huo, F. J.; Ning, P.; Zhang, Y. H.; Chao, J. B.; Meng, X. M.; Yin, C. X. J. Am. Chem. Soc. 2017, 139, 3181
[7] Huo, F. J.; Sun, Y. Q.; Su, J.; Chao, J. B.; Zhi, H. J.; Yin, C. X. Org. Lett. 2009, 11, 4918.
[8] Qian, Q.; Chen, S. H.; Chen, J. L.; Liu, R.; Wang, Y. S.; Yang, X.; Ye, Y. Chin. J. Org. Chem. 2019, 39, 2089(in Chinese). (田庆, 陈双虎, 陈景龙, 刘蕊, 汪雨诗, 杨晓朋, 叶勇, 有机化学, 2019, 39, 2089.)
[9] Fowler, B. Semin. Vasc. Med. 2005, 5, 77.
[10] Seshadri, S.; Beiser, A.; Selhub, J.; Jacques, P. F.; Rosenberg, I. H. R.; D'Agostino, B.; Wilson, P. W. F.; Wolf, P. A. N. Engl. J. Med. 2002, 346, 476.
[11] Refsum, H.; Ueland, P. M.; Nygard, O.; Vollset, S. E. Annu. Rev. Med. 1998, 49, 31.
[12] van Meurs, J. B. J.; Dhonukshe-Rutten, R. A. M.; Pluijm, S. M. F.; von der Klift, M.; de Jonge, R.; Lindemans, J.; de Groot, L. C. P. G. M.; Hofman, A.; Witteman, J. C. M.; van Leeuwen, J. P. T. M.; Breteler, M. M. B.; Lips, P.; Pols, H. A. P.; Uitterlinden, A. G. N. Engl. J. Med. 2004, 350, 2033.
[13] Hong, R.; Han, G.; Fernández, J. M.; Kim, B. J.; Forbes, N. S.; Rotello, V. M. J. Am. Chem. Soc. 2006, 128, 1078.
[14] Hassan, S. S. M.; Rechnitz, G. A. Anal. Chem. 1982, 54, 1972.
[15] Hwang, C.; Sinskey, A.; Lodish, H. Science 1992, 257, 1496.
[16] Liu, Y. C.; Xiang, K. Q.; Tian, B. Z.; Zhang, J. L. Tetrahedron Lett. 2016, 57, 2478.
[17] Pan, J.; Xu, J. C.; Zhang, Y. L.; Wang, L.; Qin, C. Q.; Zeng, L. T.; Zhang, Y. Spectrochim. Acta, Part A 2016, 168, 132.
[18] Li, X. Q.; Huo, F. J.; Yue, Y. K.; Zhang, Y. B.; Yin, C. X. Sens. Actuators, B 2017, 253, 42.
[19] Xie, J. Y.; Li, C. Y.; Li, Y. F.; Fei, J. J.; Xu, F.; Yang, J. O.; Liu, J. Anal. Chem. 2016, 88, 9746.
[20] Yang, Y.; Zhao, Q.; Feng, W.; Li, F. Chem. Rev. 2013, 113, 192.
[21] Chan, J.; Dodani, S. C.; Chang, C. J. Nat. Chem. 2012, 4, 973.
[22] Yang, Z.; Cao, J.; He, Y.; Yang, J. H.; Kim, T.; Peng, X.; Kim, J. S. Chem. Soc. Rev. 2014, 43, 4563.
[23] Chen, S.; Wang, J.; Hou, P.; Liu, L.; Wang, X. J. Instrum. Anal. 2016, 35, 1004(in Chinese). (陈颂, 王静, 侯鹏, 刘磊, 王鑫, 分析测试学报, 2016, 35, 1004.)
[24] Wang, P.; Wang, Q. Q.; Huang, J. X.; Li, N.; Gu, Y. Q. Biosens. Bioelectron. 2017, 92, 583.
[25] Yu, Y. W.; Yang, J. J.; Xu, X. H.; Jiang, Y. L.; Wang, B. X. Sens. Actuators, B 2017, 251, 902.
[26] Wang, J. Y.; Liu, Z. R.; Ren, M. G.; Kong, X. Q.; Lin, W. Y. J. Mater. Chem. B 2017, 5, 134.
[27] Tong, L. L.; Qian, Y. J. Mater. Chem. B 2018, 6, 1791.
[28] Wang, L. Y.; Chen, X. G.; Cao, D. R. Sens. Actuators, B 2017, 244, 531.
[29] Zhao, J. Z.; Huang, L.; Cui, X. N.; Li, S. J.; Wu, H. J. J. Mater. Chem. B 2015, 3, 9194.
[30] Kong, F. P.; Liang, Z. Y.; Luan D. R.; Liu, X. J.; Xu, K. H.; Tang, B. Anal. Chem. 2016, 88, 6450.
[31] Xu, K. H.; Qiang, M. M.; Gao, W.; Su, R. X.; Li, N.; Gao, Y.; Xie, Y. X.; Kong, F. P.; Tang, B. Chem. Sci. 2013, 4, 1079.
[32] Ye, Z.; Duan, C.; Hu, Q.; Zhang, Y.; Qin, C. Q.; Zeng, L. T. J.Mater. Chem. B 2017, 5, 3600.
[33] Yang, J.; Lu, Y. R; Ni, W. H.; Yin, W. B.; Liu, T. H.; Chen, S. J. Instrum. Anal. 2018, 37, 1004(in Chinese). (杨晶, 卢宜然, 倪伟华, 尹博文, 刘桃花, 陈颂, 分析测试学报, 2018, 37, 1004.)
[34] Li, J. S., Zhou, W. Y.; Ouyang, X. Y.; Yu, H.; Yang, R. H.; Tan, W. H.; Yuan, J. L. Anal. Chem. 2011, 83, 1356.
Options
文章导航

/

〈 〉