An "Off-On" Fluorescent Probe for Biothiols and Its Application in Bioimaging
- Corresponding author: Yang Yutao, yutaoyang2016@163.com Li Wei, liweihebeilab@163.com
Citation:
Zhou Tingting, Yang Yutao, Zhou Keyan, Xu Wenzhi, Li Wei. An "Off-On" Fluorescent Probe for Biothiols and Its Application in Bioimaging[J]. Chinese Journal of Organic Chemistry,
;2019, 39(12): 3498-3504.
doi:
10.6023/cjoc201906004
Zhang, S.; Ong, C. N.; Shen, H. M. Cancer Lett. 2004, 208, 143.
doi: 10.1016/j.canlet.2003.11.028
Wang, S. Q.; Shen, S. L.; Zhang, Y. R.; Dai, X.; Zhao, B. X. Chin. J. Org. Chem. 2014, 34, 1717(in Chinese).
Yan, P. P.; Wang. T.; Zhang. D.; Ma, X. Y. Chin. J. Org. Chem. 2019, 39, 916(in Chinese).
Niu, L. Y.; Chen, Y. Z.; Zheng, H. R.; Wu, L. Z.; Tung, C. H.; Yang, Q. Z. Chem. Soc. Rev. 2015, 44, 6143.
doi: 10.1039/C5CS00152H
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.
doi: 10.1038/nature09472
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
doi: 10.1021/jacs.6b12845
Huo, F. J.; Sun, Y. Q.; Su, J.; Chao, J. B.; Zhi, H. J.; Yin, C. X. Org. Lett. 2009, 11, 4918.
doi: 10.1021/ol901951h
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).
Fowler, B. Semin. Vasc. Med. 2005, 5, 77.
doi: 10.1055/s-2005-872394
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.
doi: 10.1056/NEJMoa011613
Refsum, H.; Ueland, P. M.; Nygard, O.; Vollset, S. E. Annu. Rev. Med. 1998, 49, 31.
doi: 10.1146/annurev.med.49.1.31
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.
doi: 10.1056/NEJMoa032546
Hong, R.; Han, G.; Fernández, J. M.; Kim, B. J.; Forbes, N. S.; Rotello, V. M. J. Am. Chem. Soc. 2006, 128, 1078.
doi: 10.1021/ja056726i
Hassan, S. S. M.; Rechnitz, G. A. Anal. Chem. 1982, 54, 1972.
doi: 10.1021/ac00249a013
Hwang, C.; Sinskey, A.; Lodish, H. Science 1992, 257, 1496.
doi: 10.1126/science.1523409
Liu, Y. C.; Xiang, K. Q.; Tian, B. Z.; Zhang, J. L. Tetrahedron Lett. 2016, 57, 2478.
doi: 10.1016/j.tetlet.2016.04.068
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.
doi: 10.1016/j.saa.2016.05.054
Li, X. Q.; Huo, F. J.; Yue, Y. K.; Zhang, Y. B.; Yin, C. X. Sens. Actuators, B 2017, 253, 42.
doi: 10.1016/j.snb.2017.06.120
Xie, J. Y.; Li, C. Y.; Li, Y. F.; Fei, J. J.; Xu, F.; Yang, J. O.; Liu, J. Anal. Chem. 2016, 88, 9746.
doi: 10.1021/acs.analchem.6b02646
Yang, Y.; Zhao, Q.; Feng, W.; Li, F. Chem. Rev. 2013, 113, 192.
doi: 10.1021/cr2004103
Chan, J.; Dodani, S. C.; Chang, C. J. Nat. Chem. 2012, 4, 973.
doi: 10.1038/nchem.1500
Yang, Z.; Cao, J.; He, Y.; Yang, J. H.; Kim, T.; Peng, X.; Kim, J. S. Chem. Soc. Rev. 2014, 43, 4563.
doi: 10.1039/C4CS00051J
Chen, S.; Wang, J.; Hou, P.; Liu, L.; Wang, X. J. Instrum. Anal. 2016, 35, 1004(in Chinese).
Wang, P.; Wang, Q. Q.; Huang, J. X.; Li, N.; Gu, Y. Q. Biosens. Bioelectron. 2017, 92, 583.
doi: 10.1016/j.bios.2016.10.056
Yu, Y. W.; Yang, J. J.; Xu, X. H.; Jiang, Y. L.; Wang, B. X. Sens. Actuators, B 2017, 251, 902.
doi: 10.1016/j.snb.2017.05.150
Wang, J. Y.; Liu, Z. R.; Ren, M. G.; Kong, X. Q.; Lin, W. Y. J. Mater. Chem. B 2017, 5, 134.
doi: 10.1039/C6TB02610A
Tong, L. L.; Qian, Y. J. Mater. Chem. B 2018, 6, 1791.
doi: 10.1039/C7TB03199H
Wang, L. Y.; Chen, X. G.; Cao, D. R. Sens. Actuators, B 2017, 244, 531.
doi: 10.1016/j.snb.2017.01.024
Zhao, J. Z.; Huang, L.; Cui, X. N.; Li, S. J.; Wu, H. J. J. Mater. Chem. B 2015, 3, 9194.
Kong, F. P.; Liang, Z. Y.; Luan D. R.; Liu, X. J.; Xu, K. H.; Tang, B. Anal. Chem. 2016, 88, 6450.
doi: 10.1021/acs.analchem.6b01135
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.
doi: 10.1039/c2sc22076h
Ye, Z.; Duan, C.; Hu, Q.; Zhang, Y.; Qin, C. Q.; Zeng, L. T. J.Mater. Chem. B 2017, 5, 3600.
doi: 10.1039/C7TB00489C
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.
Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb2+ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
Xinyi Hong , Tailing Xue , Zhou Xu , Enrong Xie , Mingkai Wu , Qingqing Wang , Lina Wu . Non-Site-Specific Fluorescent Labeling of Proteins as a Chemical Biology Experiment. University Chemistry, 2024, 39(4): 351-360. doi: 10.3866/PKU.DXHX202310010
Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
Jinghan ZHANG , Guanying CHEN . Progress in the application of rare-earth-doped upconversion nanoprobes in biological detection. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2335-2355. doi: 10.11862/CJIC.20240249
Yue WANG , Zhizhi GU , Jingyi DONG , Jie ZHU , Cunguang LIU , Guohan LI , Meichen LU , Jian HAN , Shengnan CAO , Wei WANG . Effects of kelp-derived carbon dots on embryonic development of zebrafish. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1209-1217. doi: 10.11862/CJIC.20230423
Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu2+. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe3+ and Cu2+ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
(a1-3) Image of cells in the absence of probe CO-NBS, (b1-3) image of cells which were incubated with probe CO-NBS (10 μmol/L) for 30 min, (c1-3) the cells were pretreated with NEM (1 mmol/L), (d1-3, e1-3, f1-3) the cells were pretreated with NEM (1 mmol/L) for 30 min and then incubated with Cys, Hcy and GSH (1 mmol/L) for 30 min and probe CO-NBS (10 μmol/L) for 30 min subsequently. Emission was collected at 493~591 nm, excited at 458 nm, scale bar: 40 μm