SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2016 , Vol. 36 >Issue 7: 1539 - 1554

DOI: https://doi.org/10.6023/cjoc201511038

Reviews

Recent Progress in Fluorescent Probes for the Detection of Hypochlorous Acid

  • Wang Yanbao ,
  • Zhao Baoxiang
Expand
  • a. Department of Chemistry and Chemical Engineering, Jining University, Qufu 273155;
    b. School of Chemistry and Chemical Engineering, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100

Received date: 2015-11-19

  Revised date: 2016-03-07

  Online published: 2016-03-18

Fold

Abstract

Hypochlorous acid (HClO) is one of the biologically important reactive oxygen species (ROS), which plays important roles in the human immune defence system, and contributes to the destruction of invading bacteria and pathogens. But excessive formation of HClO can lead to tissue damage and a series of human diseases, such as atherosclerosis, arthritis and even cancers, etc. Therefore, a rapid, sensitive, and selective detection of HClO in biological samples is important. In recent years, fluorescent probes for HClO have been developed due to various advantages such as simplicity of operation, lower limit of detection, low toxicity, high sensitivity and selectivity. A general overview of the recent research on the design, synthesis and application of fluorescent probes for hypochlorous acid is provided.

Key words： hypochlorous acid; fluorescent probe; reactive oxygen species; bioimaging

Cite this article

Wang Yanbao , Zhao Baoxiang . Recent Progress in Fluorescent Probes for the Detection of Hypochlorous Acid[J]. Chinese Journal of Organic Chemistry, 2016 , 36(7) : 1539 -1554 . DOI: 10.6023/cjoc201511038

References

[1] Dickinson, B. C.; Huynh, C.; Chang, C. J. J. Am. Chem. Soc. 2010, 132, 5906.
[2] Zielonka, J.; Sikora, A.; Hardy, M.; Joseph, J.; Dranka, B. P.; Kalyanaraman, B. Chem. Res. Toxicol. 2012, 25, 1793.
[3] Zhu, H. J.; Xu, H. D.; Yan, Y. H.; Zhang, K.; Yu, T.; Jiang, H.; Wang, S. H. Sens. Actuators, B 2014, 202, 667.
[4] Yuan, L.; Lin, W. Y.; Chen, H. Biomaterials 2013, 34, 9566.
[5] Winterbourn, C. C. Biochim. Biophys. Acta 2014, 1840, 730.
[6] Kettle, A. J.; Albrett, A. M.; Chapman, A. L.; Dickerhof, N.; Forbes, L. V.; Khalilova, I.; Turner, R. Biochim. Biophys. Acta 2014, 1840, 781.
[7] Patterson, E. K.; Fraser, D. D.; Capretta, A.; Potter, R. F.; Cepinskas, G. Free Radical Biol. Med. 2014, 70, 167.
[8] Xiao, H. D.; Xin, K.; Dou, H. F.; Yin, G.; Quan, Y. W.; Wang, R. Y. Chem. Commun. 2015, 51, 1442.
[9] Yue, Y. K.; Yin, C. X.; Huo, F. J.; Chao, J. B.; Zhang, Y. B. Sens. Actuators, B 2014, 202, 551.
[10] Zhang, R.; Song, B.; Dai, Z. C.; Ye, Z. Q.; Xiao, Y. N.; Liu, Y.; Yuan, J. L. Biosens. Bioelectron. 2013, 50, 1.
[11] Wu, Z. S.; Wu, X. J.; Li, Z.; Yang, Y. H.; Han, J. H.; Han, S. F. Bioorg. Med. Chem. Lett. 2013, 23, 4354.
[12] Aiken, M. L.; Painter, R. G.; Zhou, Y.; Wang, G. S. Free Radical Biol. Med. 2012, 53, 2308.
[13] Petrônio, M. S.; Ximenes, V. F. Biochim. Biophys. Acta 2012, 1824, 1090.
[14] Goswami, S.; Maity, S.; Maity, A. C.; Das, A. K. Sens. Actuators, B 2014, 204, 741.
[15] Ellis, D.; Thomas, R. C. Nature 1976, 262, 224.
[16] Zhang, R. G.; Kelen, S. G.; LaManna, J. C. J. Appl. Phys. 1990, 68, 1101.
[17] Hesse, S. J. A.; Ruijter, G. J. G.; Dijkema, C.; Vissser, J. J. Biotechnol. 2000, 77, 5.
[18] Huang, Y. Y.; Wang, M. J.; Yang, Z.; She, M. Y.; Wang, S.; Liu, P.; Li, J. L.; Shi, Z. Chin. Chem. Lett. 2014, 25, 1077.
[19] Zhang, D. Q. Spectrochim. Acta A 2010, 77, 397.
[20] Uno, S.; Kamiya, M.; Yoshihara, T.; Sugawara, K.; Okabe, K.; Tarhan, M. C.; Fujita, H.; Funatsu, T.; Okada, Y.; Tobita, S.; Urano, Y. Nat. Chem. 2014, 6, 681.
[21] Yang, Y. T.; Yin, C. X.; Huo, F. J.; Chao, J. B.; Zhang, Y. B.; Jin, S. Sens. Actuators, B 2014, 199, 226.
[22] Ximenes, V. F.; Fonseca, L. M.; Almeida, A. C. Arch. Biochem. Biophys. 2011, 507, 315.
[23] Dickinson, B. C.; Srikun, D.; Chang, C. J. Curr. Opin. Chem. Biol. 2010, 14, 50.
[24] Painter, R. G.; Marrero, L.; Lombard, G. A.; Valentine, V. G.; Nauseef, W. M.; Wang, G. S. J. Leukoc. Biol. 2010, 87, 933.
[25] Yang, Y. C.; Lu, H. H.; Wang, W. T.; Liau, I. Anal. Chem. 2011, 83, 8267.
[26] Kim, G.; Lee, Y. E. K.; Xu, H.; Philbert, M. A.; Kopelman, R. Anal. Chem. 2010, 82, 2165.
[27] Shi, W.; Ma, H. M. Chem. Commun. 2012, 48, 8732.
[28] Zheng, H.; Zhan, X. Q.; Bian, Q. N.; Zhang, X. J. Chem. Commun. 2013, 49, 429.
[29] Wang, B. S.; Li, P.; Yu, F. B.; Chen, J. S.; Qu, Z. J.; Han, K. L. Chem. Commun. 2013, 49, 5790.
[30] Zhang, Q. J.; Zhu, Z. C.; Zheng, Y. L.; Cheng, J. G.; Zhang, N.; Long, Y. T.; Zheng, J.; Qian, X. H.; Yang, Y. J. J. Am. Chem. Soc. 2012, 134, 18479.
[31] Chen, G.; Song, F.; Wang, J.; Yang, Z.; Sun, S.; Fan, J.; Qiang, X.; Wang, X.; Dou, B.; Peng, X. Chem. Commun. 2012, 48, 2949.
[32] Ding, Y. B.; Tang, Y. Y.; Zhu, W. H.; Xie, Y. S. Chem. Soc. Rev. 2015, 44, 1101.
[33] Xie Y.S.; Wei. P. C.; Li, X.; Hong, T.; Zhang, K.; Furuta, H. J. Am. Chem. Soc. 2013, 135, 19119.
[34] Ding, Y. B.; Li, X.; Li, T.; Zhu, W. H.; Xie, Y. S. J. Org. Chem. 2013, 78, 5328.
[35] Chen, B.; Ding, Y. B.; Li, X.; Zhu, W. H.; Hill, J. P.; Ariga, K.; Xie, Y. S. Chem. Commun. 2013, 49, 10136.
[36] Xie, Y. S.; Ding, Y. B.; Li, X.; Wang, C.; Hill, J. P.; Ariga, K.; Zhang, W. B.; Zhu, W. H. Chem. Commun. 2012, 48, 11513.
[37] Ding, Y. B.; Xie, Y. S; Li, X.; Hill, J. P.; Zhang, W. B.; Zhu, W. H. Chem. Commun. 2011, 47, 5431.
[38] 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.)
[39] Chen, Z. L.; Li, H. L.; Wei, J.; Xiao, Y.; Yu, H. B. Chin. J. Org. Chem. 2015, 35, 789 (in Chinese). (陈忠林, 李红玲, 韦驾, 肖义, 于海波, 有机化学, 2015, 35, 789.)
[40] He, Y.; Feng, R. K.; Yi, Y. R.; Liu, Z. X. Chin. J. Org. Chem. 2014, 34, 2236 (in Chinese). (何源, 冯若昆, 易云瑞, 刘占祥, 有机化学, 2014, 34, 2236.)
[41] Xu, Q. C.; Jin, C.; Zhu, X. H.; Xing, G. W. Chin. J. Org. Chem. 2014, 34, 647 (in Chinese). (徐勤超, 金灿, 朱雪慧, 邢国文, 有机化学, 2014, 34, 647.)
[42] Huang, Y. Y.; Wang, M. J.; She, M. Y.; Yang, Z.; Liu, P.; Li, J. L.; Shi, Z. Chin. J. Org. Chem. 2014, 34, 1 (in Chinese). (黄阳阳, 王梦嘉, 厍梦尧, 杨征, 刘萍, 李剑利, 史真, 有机化学, 2014, 34, 1.)
[43] Dickinson, B. C.; Chang, C. J. Nat. Chem. Biol. 2011, 7, 504.
[44] Cheng, X.; Jia, H.; Long, T.; Feng, J.; Qin, J.; Li, Z. Chem. Commun. 2011, 47, 11978.
[45] Egawa, T.; Koide, Y.; Hanaoka, K.; Komatsu, T.; Terai, T.; Nagano, T. Chem. Commun. 2011, 47, 4162.
[46] Liu, S. R.; Vedamalai, M.; Wu, S. P. Anal. Chim. Acta. 2013, 800, 71.
[47] Gai, L. Z.; Mack, J.; Liu, H.; Xu, Z.; Lu, H.; Li, Z. F. Sens. Actuators, B 2013, 182, 1.
[48] Zhu, H.; Fan, J. L.; Wang, J. Y.; Mu, H. Y.; Peng, X. J. J. Am. Chem. Soc. 2014, 136, 12820.
[49] Park, J.; Kim, H.; Choi, Y.; Kim, Y. Analyst 2013, 138, 3368.
[50] Emrullaho?lu, M.; Üçüncü, M.; Karaku?, E. Chem. Commun. 2013, 49, 7836.
[51] Hu, J. J.; Wong, N. K.; Gu, Q. S.; Bai, X. Y.; Ye, S.; Yang, D. Org. Lett. 2014, 16, 3544.
[52] Liu, S. R.; Wu, S. P. Org. Lett. 2013, 15, 878.
[53] Venkatesan, P.; Wu, S. P. Analyst 2015, 140, 1349.
[54] Yuan, L.; Lin, W. Y.; Yang, Y. T.; Chen, H. J. Am. Chem. Soc. 2012, 134, 1200.
[55] Zhang, Z.; Zheng, Y.; Hang, W.; Yan, X. M.; Zhao, Y. F. Talanta 2011, 85, 779.
[56] Zhan, X. Q.; Yan, J. H.; Su, J. H.; Wang, Y. C.; He, J.; Wang, S. Y.; Zheng, H.; Xu, J. G. Sens. Actuators, B 2010, 150, 774.
[57] Koide, Y.; Urano, Y.; Hanaoka, K.; Terai, T.; Nagano, T. J. Am. Chem. Soc. 2011, 133, 5680.
[58] Hu, Z. Q.; Zhu, J. H.; Gu, Y. Y.; Hu, W. Z.; Li, M.; Jiang, Y. Microchim. Acta 2014, 181, 1401.
[59] Yuan, L.; Lin, W. Y.; Xie, Y. N.; Chen, B.; Song, J. Z. Chem. Eur. J. 2012, 18, 2700.
[60] Zuo, Q. P.; Li, Z. J.; Hu, Y. H.; Li, B.; Huang, L. H.; Wang, C. J.; Liu, S. K.; Liao, H. Q. J. Fluoresc. 2012, 22, 1201.
[61] Zhang, Z.; Deng, C. Q.; Meng, L. S.; Zheng, Y.; Yan, X. M. Anal. Methods 2015, 7, 107.
[62] Zhou, J.; Li, L. H.; Shi, W.; Gao, X. H.; Li, X. H.; Ma, H. M. Chem. Sci. 2015, 6, 4884.
[63] Liu, Y. L.; Sun, Y.; Du, J.; Lv, X.; Zhao, Y.; Chen, M. L.; Wang, P.; Guo, W. Org. Biomol. Chem. 2011, 9, 432.
[64] Zhang, Y. R.; Meng, N.; Miao, J. Y.; Zhao, B. X. Chem. Eur. J. 2015, 21, 19058.
[65] Tang, Z; Ding, X. L.; Liu, Y.; Zhao Z. M. Zhao, B. X. RSC Adv. 2015, 5, 99664.
[66] Chan, J.; Dodani, S. C.; Chang, C. J. Nat. Chem. 2012, 4, 973.
[67] Xu, Q. L.; Lee, K. A.; Lee, S.; Lee, K. M.; Lee, W. J.; Yoon, J. J. Am. Chem. Soc. 2013, 135, 9944.
[68] Huo, F. J.; Zhang, J. J.; Yang, Y. T.; Chao, J. B.; Yin, C. X.; Zhang, Y. B.; Chen, T. G. Sens. Actuators, B 2012, 166, 44.
[69] Best, Q. A.; Sattenapally, N.; Dyer, D. J.; Scott, C. N.; McCarroll, M. E. J. Am. Chem. Soc. 2013, 135, 13365.
[70] Jin, X. L.; Hao, L. K.; Hu, Y. L.; She, M. Y.; Shi, Y. N.; Obst, M.; Li, J. L.; Shi, Z. Sens. Actuators, B 2013, 186, 56.
[71] Yin, W. Z.; Zhu, H. J.; Wang, R. Y. Dyes Pigm. 2014, 107, 127.
[72] Mujumdar, R. B.; Ernst, L. A.; Mujumdar, S. R.; Lewis, C. J.; Waggoner, A. S. Bioconjug. Chem. 1993, 4, 105.
[73] Lou, Z. R.; Li, P.; Song, P.; Han, K. L. Analyst. 2013, 138, 6291.
[74] Cheng, G. H.; Fan, J. L.; Sun, W.; Cao, J. F.; Hu, C.; Peng, X. J. Chem. Commun. 2014, 50, 1018.
[75] Sun, M. T.; Yu, H.; Zhu, H. J.; Ma, F.; Zhang, S.; Huang, D. J.; Wang, S. H. Anal. Chem. 2014, 86, 671.
[76] Zhang, W. J.; Guo, C.; Liu, L. H.; Qin, J. G.; Yang, C. L. Org. Biomol. Chem. 2011, 9, 5560.
[77] Zhang, W. J.; Liu, L. H.; Liu, L.; Qin, J. G.; Yang, C. L. Polym. Chem. 2012, 50, 1174.
[78] Zhang, W. J.; Li, C. G.; Qin, J. G.; Yang, C. L. Polymer 2012, 53, 2356.
[79] Wysockia, L. M.; Lavis, L. D. Curr. Opin. Chem. Biol. 2011, 15, 752.
[80] Yu, S. Y.; Hsu, C. Y.; Chen, W. C.; Wei, L. F.; Wu, S. P. Sens. Actuators, B 2014, 196, 203.
[81] Li, G. P.; Zhu, D. J.; Liu, Q.; Xue, L.; Jiang, H. Org. Lett. 2013, 15, 2002.
[82] Zhang, Y. R.; Chen, X. P.; Shao, J.; Zhang, J. Y.; Yuan, Q.; Miao, J. Y.; Zhao, B. X. Chem. Commun. 2014, 50, 14241.
[83] Hou, J. T.; Li, K.; Yang, J.; Yu, K. K.; Liao, Y. X.; Ran, Y. Z.; Liu, Y. H.; Zhou, X. D.; Yu, X. Q. Chem. Commun. 2015, 51, 6781.
[84] Zhang, Y. R.; Zhao, Z. M.; Su, L.; Miao, J. Y.; Zhao, B. X. RSC Adv. 2016, 6, 17059.
[85] Terai, T.; Nagano, T. Pflugers Arch. 2013, 465, 347.
[86] Yu, X. J.; Zhang, W. Z.; Ye, Z. Q.; Song, B.; Yuan, J. L. J Fluoresc, 2015, 5, 1581.
[87] Yuan , L.; Lin, W. Y.; Song, J. Z.; Yang, Y. T. Chem. Commun. 2011, 47, 12691.
[88] Liu, F. Y.; Gao, Y. L.; Wang, J. T.; Sun, S. G. Analyst 2014, 139, 3324.
[89] Zhang, R.; Ye, Z. Q.; Song, B.; Dai, Z. C.; An, X.; Yuan, J. L. Inorg. Chem. 2013, 52, 10325.
[90] Ye, Z. Q.; Zhang, R.; Song, B.; Dai, Z. C.; Jin, D. Y.; Goldys, E. M.; Yuan, J. L. Dalton Trans. 2014, 43, 8414.
[91] Xiao, Y. N.; Zhang, R.; Ye, Z. Q.; Dai, Z. C.; An, H. Y.; Yuan, J. L. Anal. Chem. 2012, 84, 10785.
[92] Shi, J.; Li, Q. Q.; Zhang, X.; Peng, M.; Qin, J. G.; Li, Z. Sens. Actuators, B 2010, 145, 583.
[93] Liao, Y. X.; Wang, M. D.; Li, K.; Yang, Z. X.; Hou, J. T.; Wu, M. Y.; Liu, Y. H.; Yu, X. Q. RSC Adv., 2015, 5, 18275.
[94] Zhang, W.; Liu, W.; Li, P.; Kang, J. Q.; Wang, J. Y.; Wang, H.; Tang, B. Chem. Commun. 2015, 51, 10150.
[95] Li, J. F.; Huo, F. J.; Yin, C. X. RSC Adv. 2014, 4, 44610.
[96] Li, D. X.; Feng, Y.; Lin, J. Z.; Chen, M.; Wang, S. X.; Wang, X.; Sheng, H. T.; Shao, Z. L.; Zhu, M. Z.; Meng, X. M. Sens. Actuators, B 2016, 222, 483.
[97] Xu, Q. L.; Heo, C. H.; Kim, G. H.; Lee, W.; Kim, H. M.; Yoon, J. Angew. Chem., Int. Ed. 2015, 54, 4890.
[98] Wang, X. M.; Wang, X. H.; Feng, Y.; Zhu, M. Z.; Yin, H.; Guo, Q. X.; Meng, X. M. Dalton Trans. 2015, 44, 6613.
[99] Yuan, L.; Wang, L.; Agrawalla, B. K.; Park, S. J.; Zhu, Ha.; Sivaraman, B.; Peng, J. J.; Xu, Q. H.; Chang, Y. T. J. Am. Chem. Soc. 2015, 137, 5930.

Options
Outlines

/

〈 〉