综述与进展

次氯酸比色荧光探针的研究进展

  • 余青 ,
  • 陈晓丽 ,
  • 刘华 ,
  • 张奇龙
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  • 贵州医科大学基础医学院 贵阳 550025

收稿日期: 2019-11-04

  修回日期: 2019-12-21

  网络出版日期: 2020-01-15

基金资助

贵州省科学技术基金(Nos.[2019]2792,[2018]5779-14)资助项目.

Recent Progress in Colorimetric and Fluorimetric Probes for the Detection of Hypochlorous Acid

  • Yu Qing ,
  • Chen Xiaoli ,
  • Liu Hua ,
  • Zhang Qilong
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  • Guizhou Medical University, School of Basic Medicine, Guiyang 550025

Received date: 2019-11-04

  Revised date: 2019-12-21

  Online published: 2020-01-15

Supported by

Project supported by the Science and Technology Foundation of Guizhou Province (Nos. [2019]2792, [2018]5779-14).

摘要

次氯酸(HClO)和次氯酸钠(NaClO)广泛存在于生命体和环境中,并与生命体的健康或疾病密切相关.近年来,为揭示HClO对生物体的作用及作用机制,已经设计出许多HClO比色荧光探针,这些次氯酸比色荧光探针由于具有灵敏、快速、高选择性、可视化和实时监测等优点而被用于环境或生物体中HClO或ClO-的检测.根据探针对HClO识别机制的不同,将HClO比色荧光探针分为五大类,总结评价近五年来次氯酸比色荧光探针的设计、特征及实际应用.

本文引用格式

余青 , 陈晓丽 , 刘华 , 张奇龙 . 次氯酸比色荧光探针的研究进展[J]. 有机化学, 2020 , 40(5) : 1206 -1231 . DOI: 10.6023/cjoc201911004

Abstract

Hypochlorous acid (HClO) and sodium hypochlorite (NaClO) exist widely in living organisms and environment and is closely related to the health or disease of living organisms. In recent years, in order to reveal the effect and mechanism of HClO on living organisms, many HClO colorimetric and fluorimetric probes have been designed and applied to the detection HClO or ClO- in environment or living organisms due to their sensitivity, rapidity, high selectivity and real-time monitoring. According to the different recognition mechanism of probes for HClO, HCO colorimetric fluorescent probes are divided into five categories. The design, characteristics and practical application of hypochlorite colorimetric fluorescent probes in the past five years are summarized and evaluated.

参考文献

[1] Steinbeck, M. J.; Nesti, L. J.; Sharkey, P. F.; Javad, P. J. Orthop. Res. 2010, 25, 1128.
[2] Strzepa, A.; Pritchard, K. A.; Dittel, B. N. Cell Immunol. 2017, 317, 142.
[3] Shi, L.; Li, X.; Zhou, M.; Muhammad, F.; Ding, Y.; Wei, H. Analyst 2017, 142, 2104.
[4] Liu, Z.; Jiang, T.; Wang, B.; Ke, B.; Zhou, Y.; Du, L.; Li, M. Anal. Chem. 2016, 88, 1511.
[5] Mohammadi, A.; Dehghan, Z.; Rassa, M.; Chaibakhsh, N. Sens. Actuators, B 2016, 230, 388.
[6] Kim, H. N.; Ren, W. X.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2012, 41, 3210.
[7] Jung, Y. K.; Park, H. G. Biosens. Bioelectron. 2015, 72, 127.
[8] Abnous, K.; Danesh, N. M.; Ramezani, M.; Emrani, A. S.; Taghdisi, S. M. Biosens. Bioelectron. 2016, 78, 80.
[9] Kim, S. K.; Lee, D. H.; Hong, J. I. Acc. Chem. Res. 2009, 42, 23.
[10] Cui, K.; Zhang, D.; Zhang, G.; Zhu, D. Tetrahedron Lett. 2010, 51, 6052.
[11] Zhang, W.; Guo, C.; Liu, L.; Qin, J.; Yang, C. Org. Biomol. Chem. 2011, 9, 5560.
[12] Cheng, X.; Jia, H.; Long, T.; Feng, J.; Qin, J.; Li, Z. Chem. Commun. 2011, 47, 11978.
[13] Zhou, Y.; Pei, W.; Wang, C.; Zhu, J.; Wu, J.; Yan, Q.; Zhang, Q. Small 2014, 10, 3560.
[14] Cao, L.; Zhang, R.; Zhang, W.; Du, Z.; Liu, C.; Ye, Z.; Yuan, J. Biomaterials 2015, 68, 21.
[15] Lu, F.; Nabeshima, T. Dalton Trans. 2014, 43, 9529.
[16] Zhao, C.; An, J.; Zhou, L.; Fei, Q.; Wang, F.; Tan, J.; Zhu, W. H. Chem. Commun. 2015, 52, 2075.
[17] Xiao, H.; Xin, K.; Dou, H.; Yin, G.; Quan, Y.; Wang, R. Chem. Commun. 2015, 51, 1442.
[18] Sun, M.; Yu, H.; Zhu, H.; Ma, F.; Zhang, S.; Huang, D.; Wang, S. Anal. Chem. 2014, 86, 671.
[19] Wang, Y. B.; Zhao, B. X. Chin. J. Org. Chem. 2016, 36, 1539(in Chinese). (王延宝, 赵宝祥, 有机化学, 2016, 36, 1539.)
[20] Zhang, Y. R.; Liu, Y.; Feng, X.; Zhao, B. X. Sens. Actuators, B 2017, 240, 18.
[21] Shen, Y.; Zhang, X.; Huang, X.; Wen, S.; Liu, M.; Deng, Y.; Yao, S. RSC Adv. 2015, 5, 1039.
[22] Cao, J.; Jiang, D. M.; Ren, X.; Li, T.; Gong, X. T.; Yang, Y. R.; Zhang, H. L. Dyes Pigm. 2017, 146, 279.
[23] Choi, M. G.; Ryu, H.; Cho, M. J.; Lee, S. K.; Chang, S. K. Sens. Actuators, B 2017, 244, 307.
[24] Soni, D.; Gangada, S.; Duvva, N.; Roy, T. K.; Nimesh, S.; Arya, G.; Chitta, R. New J. Chem. 2017, 41, 5322.
[25] Wu, L.; Wu, I. C.; DuFort, C. C.; Carlson, M. A.; Wu, X.; Chen, L.; Chiu, D. T. J. Am. Chem. Soc. 2017, 139, 6911.
[26] Yin, C.; Zhen, X.; Fan, Q.; Huang, W.; Pu, K. ACS Nano 2017, 11, 4174.
[27] Zhang, B.; Yang, X.; Zhang, R.; Liu, Y.; Ren, X.; Xian, M.; Ye, Y.; Zhao, Y. Anal. Chem. 2017, 89, 10384.
[28] Feng, H.; Meng, Q.; Wang, Y.; Duan, C.; Wang, C.; Jia, H.; Zhang, R. Chem.-Asian. J. 2018, 13, 2611.
[29] He, L.; Zhang, Y.; Xiong, H.; Wang, J.; Geng, Y.; Wang, B.; Song, X. Dyes Pigm. 2019, 166, 390.
[30] Song, H.; Zhou, Y.; Xu, C.; Wang, X.; Zhang, J.; Wang, Y.; Peng, X. Dyes Pigm. 2019, 162, 160.
[31] Wu, X.; Li, Z.; Yang, L.; Han, J.; Han, S. Chem. Sci. 2013, 4, 460.
[32] Liu, F.; Tang, Y.; Kuang, Y.; Pan, D., Liu, X.; Yu, R. Q.; Jiang, J. H. RSC Adv. 2016, 6, 107910.
[33] Lin, Q. S.; Huang, Y. L.; Fan, X. X.; Zheng, X. L.; Chen, X. L.; Zhan, X. Q.; Zheng, H. Talanta 2017, 170, 496.
[34] Shen, S. L.; Huang, X. Q.; Zhang, Y. Y.; Zhu, Y.; Hou, C.; Ge, Y. Q.; Cao, X. Q. Sens. Actuators, B 2018, 263, 252.
[35] Shen, S. L.; Huang, X. Q.; Jiang, H. L.; Lin, X. H.; Cao, X. Q. Anal. Chim. Acta 2019, 1046, 185.
[36] Yao, S. K.; Qian, Y. Sens. Actuators, B 2017, 252, 877.
[37] Gong, Y. J.; Lv, M. K.; Zhang, M. L.; Kong, Z. Z.; Mao, G. J. Talanta 2019, 192, 128.
[38] Wu, Z.; Wu, X.; Li, Z.; Yang, Y.; Han, J.; Han, S. Bioorg. Med. Chem. Lett. 2013, 23, 4354.
[39] Mei, Q.; Deng, W.; Yisibashaer, W.; Jing, H.; Du, G.; Wu, M.; Zhang, Y. Small 2015, 11, 4568.
[40] Zhu, B.; Wu, L.; Zhang, M.; Zhao, Z.; Wang, Z.; Duan, Q.; Liu, C. Sens. Actuators, B 2018, 267, 589.
[41] Wu, G.; Zeng, F.; Wu, S. Anal. Methods 2013, 5, 5589.
[42] Cheng, G.; Fan, J.; Sun, W.; Sui, K.; Jin, X.; Wang, J.; Peng, X. Analyst 2013, 138, 6091.
[43] Guo, B.; Nie, H.; Yang, W.; Tian, Y.; Jing, J.; Zhang, X. Sens. Actuators, B 2016, 236, 459.
[44] Xu, X. X.; Qian, Y. Spectrochim. Acta, Part A 2017, 183, 356.
[45] Goswami, S.; Das, S.; Aich, K.; Nandi, P. K.; Ghoshal, K.; Quah, C. K.; Abdel-Aziz, H. A. RSC Adv. 2014, 4, 24881.
[46] Goswami, S.; Das, A. K.; Manna, A.; Maity, A. K.; Saha, P.; Quah, C. K.; Abdel-Aziz, H. A. Anal. Chem. 2014, 86, 6315.
[47] Long, Y.; Zhou, J.; Yang, M. P.; Liu, X. J.; Zhang, M.; Yang, B. Q. Sens. Actuators, B 2016, 232, 327.
[48] Ren, M.; Deng, B.; Zhou, K.; Kong, X.; Wang, J. Y.; Xu, G.; Lin, W. J. Mater. Chem. B 2016, 4, 4739.
[49] Xia, Y.; Liu, X.; Wang, D.; Wang, Z.; Liu, Q.; Yu, H.; Song, Y. Chin. Chem. Lett. 2018, 29, 1517.
[50] Shen, S. L.; Zhao, X.; Zhang, X. F.; Liu, X. L.; Wang, H.; Dai, Y. Y.; Zhao, B. X. J. Mater. Chem. B 2017, 5, 289.
[51] Zhu, J. H.; Wong, K. M. C. Sens. Actuators, B 2018, 267, 208
[52] Lee, H. J.; Cho, M. J.; Chang, S. K. Inorg. Chem. 2015, 54, 8644.
[53] Zhang, R.; Liang, L.; Meng, Q.; Zhao, J.; Ta, H. T.; Li, L.; Zhang, Z.; Sultanbawa, Y.; Xu, Z. P. Small 2019, 15, 1803712.
[54] Wu, J.; Liu, W.; Ge, J.; Zhang, H.; Wang, P. Chem. Soc. Rev. 2011, 40, 3483.
[55] Chen, W. C.; Venkatesan, P.; Wu, S. P. Anal. Chim. Acta 2015, 882, 68.
[56] Wang, E.; Qiao, H.; Zhou, Y.; Pang, L.; Yu, F.; Zhang, J.; Ma, T. RSC Adv. 2015, 5, 73040.
[57] Qiao, L.; Nie, H.; Wu, Y.; Xin, F.; Gao, C.; Jing, J.; Zhang, X. J. Mater. Chem. B 2017, 5, 525.
[58] Zang, L.; Liang, C.; Wang, Y.; Bu, W.; Sun, H.; Jiang, S. Sens. Actuators, B 2015, 211, 164.
[59] Wang, B.; Chen, D.; Kambam, S.; Wang, F.; Wang, Y.; Zhang, W.; Chen, X. Dyes Pigm. 2015, 120, 22.
[60] Li, J.; Yang, X.; Zhang, D.; Liu, Y.; Tang, J.; Li, Y.; Ye, Y. Sens. Actuators, B 2018, 265, 84.
[61] Wu, W. L.; Zhao, Z. M.; Dai, X.; Su, L.; Zhao, B. X. Sens. Actuators, B 2016, 232, 390.
[62] Jia, H.; Xia, S.; Feng, H.; Meng, Q.; Duan, C.; Zhang, Z.; Zhang, R. Org. Biomol. Chem. 2018, 16, 2074.
[63] Goswami, S.; Aich, K.; Das, S.; Pakhira, B.; Ghoshal, K.; Quah, C. K., Sarkar, S. Chem.-Asian J. 2015, 10, 694.
[64] Ning, Y.; Cui, J.; Lu, Y.; Wang, X.; Xiao, C.; Wu, S.; Zhang, Y. Sens. Actuators, B 2018, 269, 322.
[65] Wang, Y.; Xia, J.; Han, J.; Bao, X.; Li, Y.; Tang, X.; Gao, M. Talanta 2016, 161, 847.
[66] Yang, Y.; Gao, C. Y.; Chen, J.; Zhang, N.; Dong, D. Anal. Methods 2016, 8, 805.
[67] Chen, B.; Fu, H.; Lv, Y.; Li, X.; Han, Y. Tetrahedron Lett. 2018, 59, 1116.
[68] Das, S.; Aich, K.; Patra, L.; Ghoshal, K.; Gharami, S.; Bhattacharyya, M.; Mondal, T. K. Tetrahedron Lett. 2018, 59, 1130.
[69] Feng, H.; Zhang, Z.; Meng, Q.; Jia, H.; Wang, Y.; Zhang, R. Adv. Sci. 2018, 5, 1800397.
[70] Yan, L.; Hu, C.; Li, J. Anal. Bioanal. Chem. 2018, 410, 7457.
[71] Huo, F.; Zhang, Y.; Yin, C. Sens. Actuators, B 2018, 269, 180.
[72] Yan, F.; Fan, K.; Ma, T.; Xu, J.; Wang, J.; Ma, C. Spectrochim. Acta, Part A 2019, 213, 254.
[73] Zhang, Z.; Fan, J.; Cheng, G.; Ghazali, S.; Du, J.; Peng, X. Sens. Actuators, B 2017, 246, 293.
[74] Xu, C.; Qian, Y. Dyes Pigm. 2019, 161, 303.
[75] Lou, Z.; Li, P.; Song, P.; Han, K. Analyst 2013, 138, 6291.
[76] Li, H.; Guan, L.; Zhang, X.; Yu, H.; Huang, D.; Sun, M.; Wang, S. Talanta 2016, 161, 592.
[77] Zhou, L.; Lu, D. Q.; Wang, Q.; Hu, S.; Wang, H.; Sun, H.; Zhang, X. Spectrochim. Acta, Part A 2016, 166, 129.
[78] Ma, Z.; Wang, X.; Wang, C.; Chen, X.; Lv, Q. Spectrochim. Acta, Part A 2019, 213, 370.
[79] Wu, W. L.; Zhao, X.; Xi, L. L.; Huang, M. F.; Zeng, W. H.; Miao, J. Y.; Zhao, B. X. Anal. Chim. Acta 2017, 950, 178.
[80] Zhang, L. J.; Ning, J. Y.; Miao, J. Y.; Liu, J. T.; Zhao, B. X. New J. Chem. 2018, 42, 2989.
[81] Xu, J.; Yuan, H.; Qin, C.; Zeng, L.; Bao, G. M. RSC Adv. 2016, 6, 107525.
[82] Song, X.; Dong, B.; Kong, X.; Wang, C.; Zhang, N.; Lin, W. Spectrochim. Acta, Part A 2018, 188, 394.
[83] Yan, Y. H.; Ma, H. L.; Miao, J. Y.; Zhao, B. X.; Lin, Z. M. Anal. Chim. Acta 2019, 1064, 87.
[84] Huang, Y.; Zhang, Y.; Huo, F., Chao, J.; Yin, C. Sens. Actuators, B 2019, 287, 453.
[85] Wu, W. L.; Ma, H. L.; Xi, L. L.; Huang, M. F.; Wang, K. M.; Miao, J. Y.; Zhao, B. X. Talanta 2019, 194, 308.
[86] Wu, Y.; Wang, J.; Zeng, F.; Huang, S.; Huang, J.; Xie, H.; Wu, S. ACS Appl. Mater. Interfaces 2016, 8, 1511.
[87] Hu, Q.; Qin, C.; Huang, L.; Wang, H.; Liu, Q.; Zeng, L. Dyes Pigm. 2018, 149, 253.
[88] Lv, J.; Chen, Y.; Wang, F.; Wei, T.; Zhang, Z.; Qiang, J.; Chen, X. Dyes Pigm. 2018, 148, 353.
[89] Gu, J.; Li, X.; Zhou, Z.; Liao, R.; Gao, J.; Tang, Y.; Wang, Q. Chem. Eng. J. 2019, 368, 157.
[90] Li, J.; Liu, T.; Huo, F.; Chao, J.; Zhang, Y.; Yin, C. Spectrochim. Acta, Part A 2017, 174, 17.
[91] Li, J.; Li, P.; Huo, F.; Yin, C.; Liu, T.; Chao, J.; Zhang, Y. Dyes Pigm. 2016, 130, 209.
[92] Xiao, H.; Li, J.; Zhao, J.; Yin, G.; Quan, Y.; Wang, J.; Wang, R. J. Mater. Chem. B 2015, 3, 1633.
[93] Zhang, Q.; Zhang, P.; Gong, Y.; Ding, C. Sens. Actuators, B 2019, 278, 73.
[94] Chen, H.; Sun, T.; Qiao, X. G.; Tang, Q. O.; Zhao, S. C.; Zhou, Z. Spectrochim. Acta, Part A 2018, 204, 196.
[95] Hu, J. J.; Wong, N. K.; Gu, Q.; Bai, X.; Ye, S.; Yang, D. Org. Lett. 2014, 16, 3544.
[96] Yue, Y.; Yin, C.; Huo, F.; Chao, J.; Zhang, Y. Sens. Actuators, B 2014, 202, 551-556.
[97] Guo, T.; Cui, L.; Shen, J.; Wang, R.; Zhu, W.; Xu, Y.; Qian, X. Chem. Commun. 2013, 49, 1862.
[98] Zhu, B.; Wu, L.; Zhang, M.; Wang, Y.; Liu, C.; Wang, Z.; Jia, P. Biosens. Bioelectron. 2018, 107, 218.
[99] Wang, X.; Xu, C.; Song, H.; Liu, X.; Xie, X.; Pang, X.; Zhou, Y. J. Lumin. 2019, 210, 472.
[100] Wang, Z.; Zhang, Y.; Song, J.; Li, M.; Yang, Y.; Gu, W.; Wang, S. Dyes Pigm. 2019, 161, 172.
[101] Wang, Q.; Jin, L.; Wang, W.; Dai, L.; Tan, X.; Zhao, C. Spectrochim. Acta, Part A 2019, 211, 239.
[102] Fan, J.; Mu, H.; Zhu, H.; Wang, J.; Peng, X. Analyst 2015, 140, 4594.
[103] Fan, J.; Mu, H.; Zhu, H.; Du, J.; Jiang, N.; Wang, J.; Peng, X. Ind. Eng. Chem. Res. 2015, 54, 8842.
[104] Ponnuvel, K.; Ramamoorthy, J.; Sivaraman, G.; Padmini, V. ChemistrySelect 2018, 3, 91.
[105] Xue, M.; Wang, H.; Chen, J.; Ren, J.; Chen, S.; Yang, H.; Zhang, P. Sens. Actuators, B. 2019, 282, 1.
[106] Wu, Z.; Wu, X.; Li, Z.; Yang, Y.; Han, J.; Han, S. Bioorg. Med. Chem. Lett. 2013, 23, 4354.
[107] Chen, Y.; Wei, T.; Zhang, Z.; Zhang, W.; Lv, J.; Chen, T.; Chen, X. Chin. Chem. Lett. 2017, 28, 1957.
[108] Pan, Y.; Han, Y. Tetrahedron Lett. 2017, 58, 1301.
[109] Wang, Q.; Liu, C.; Chang, J.; Lu, Y.; He, S.; Zhao, L.; Zeng, X. Dyes Pigm. 2013, 99, 733.
[110] Shu, W.; Yan, L.; Wang, Z.; Liu, J.; Zhang, S.; Liu, C.; Zhu, B. Sens. Actuators, B 2015, 221, 1130.
[111] Wang, C.; Ji, H.; Li, M.; Cai, L.; Wang, Z.; Li, Q.; Li, Z. Faraday Discuss. 2017, 196, 427.
[112] Li, J.; Yin, C.; Liu, T.; Wen, Y.; Huo, F. Sens. Actuators, B 2017, 252, 1112.
[113] Li, J.; Yin, C.; Huo, F.; Xiong, K.; Chao, J.; Zhang, Y. Sens. Actuators, B 2016, 231, 547.
[114] Jiang, Y.; Wu, S.; Jin, C.; Wang, B.; Shen, J. Sens. Actuators, B 2018, 265, 365.
[115] Wang, Z.; Zhang, Y.; Song, J.; Li, M.; Yang, Y.; Xu, X.; Wang, S. Sens. Actuators, B 2019, 284, 148.
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