A Seminaphthorhodafluor-Based Fluorescent Probe for H2S Detection and Its Application
- Corresponding author: Jia Yanlin, jiayanlin@126.com Jin Xilang, jinxilang_911@163.com
Citation:
Chen Weixing, Wang Ting, Zhang Yunfei, Li Shuying, Zhou Hongwei, Jia Yanlin, Jin Xilang. A Seminaphthorhodafluor-Based Fluorescent Probe for H2S Detection and Its Application[J]. Chinese Journal of Organic Chemistry,
;2020, 40(9): 2956-2962.
doi:
10.6023/cjoc202006001
Filipovic, M. R.; Zivanovic, J.; Alvarez, B.; Banerjee, R. Chem. Rev. 2018, 118, 1253.
doi: 10.1021/acs.chemrev.7b00205
Boehning, D.; Snyder, S. H. Ann. Rev. Neurosci. 2003, 26, 105.
doi: 10.1146/annurev.neuro.26.041002.131047
Tang, C.; Li, X.; Du, J. Curr. Vasc. Pharmacol. 2006, 4, 17.
doi: 10.2174/157016106775203144
Li, L.; Bhatia, M.; Zhu, Y. Z.; Zhu, Y. C.; Ramnath, R. D.; Wang, Z. J.; Anuar, F. B. M.; Whiteman, M.; Salto-Tellez, M.; Moore, P. K. FASEB J. 2005, 19, 1196.
doi: 10.1096/fj.04-3583fje
Zanardo, R. C. O.; Brancaleone, V.; Distrutti, E.; Fiorucci, S.; Cirino, G.; Wallace, J. L. FASEB J. 2006, 20, 2118.
doi: 10.1096/fj.06-6270fje
Fiorucci, S.; Antonelli, E.; Mencarelli, A.; Orlandi, S.; Renga, B.; Rizzo, G.; Distrutti, E.; Shah, V.; Morelli, A. Hepatology 2005, 42, 539.
doi: 10.1002/hep.20817
Kabil, O.; Banerjee, R. J. Biol. Chem. 2010, 285, 21903.
doi: 10.1074/jbc.R110.128363
Lefer, D. J. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 17907.
doi: 10.1073/pnas.0709010104
Kamoun, P.; Belardinelli, M.-C.; Chabli, A.; Lallouchi, K.; Chadefaux-Vekemans, B. Am. J. Med. Genet., Part A 2003, 116A, 310.
doi: 10.1002/ajmg.a.10847
Chen, F.; Han, D.; Liu, H.; Wang, S.; Li, K.-B.; Zhang, S.; Shi, W. Analyst 2018, 143, 440.
Jin, Y.; Liu, R.; Zhan, Z.; Lv, Y. Talanta 2019, 202, 159.
doi: 10.1016/j.talanta.2019.04.067
Zong, L.; Zhang, M.; Song, Y.; Xie, Y.; Feng, J.; Li, Q.; Li, Z. Sens. Actuators. B 2018, 257, 882.
doi: 10.1016/j.snb.2017.11.048
Ma, C.; Wei, C.; Li, X.; Zheng, X.; Chen, B.; Wang, M.; Zhang, P.; Li, X. Dyes Pigm. 2019, 162, 624.
doi: 10.1016/j.dyepig.2018.10.072
Han, L.; Shi, R.; Xin, C.; Ci, Q.; Ge, J.; Liu, J.; Wu, Q.; Zhang, C.; Li, L.; Huang, W. ACS Sens. 2018, 3, 1622.
doi: 10.1021/acssensors.8b00456
Jiao, X.; Li, Y.; Niu, J.; Xie, X.; Wang, X.; Tang, B. Anal. Chem. 2018, 90, 533.
doi: 10.1021/acs.analchem.7b04234
Chen, Y.; Bi, K. Y.; Hao, R. T.; Xie, P.; Huang, L. N.; Wang, Y. M.; Zhang, J. F.; Xu, R.; Wu, X. H. Chin. J. Org. Chem. 2020, 40, 511(in Chinese).
Tang, L.; Xia, J.; Zhong, K.; Tang, Y.; Gao, X.; Li, J. Dyes Pigm. 2020, 178, 108379.
doi: 10.1016/j.dyepig.2020.108379
He, P.; Tang, L.; Zhong, K.; Hou, S.; Yan, X. Chin. J. Org. Chem. 2017, 37, 423(in Chinese).
Zhu, H.; Liang, C.; Cai, X.; Zhang, H.; Liu, C.; Jia, P.; Li, Z.; Yu, Y.; Zhang, X.; Sheng, W.; Zhu, B. Anal. Chem. 2020, 92, 1883.
doi: 10.1021/acs.analchem.9b04009
Zhong, K.; Zhao, J.; Li, Q.; Hou, S.; Tang, Z.; Bian, Y.; Tang, L. Chin. J. Org. Chem. 2018, 38, 1786(in Chinese).
Zhao, X.-J.; Jiang, Y.-R.; Li, Y.-T.; Yang, B.-Q.; Liu, C.; Liu, Z.-H. Spectrochim. Acta. Part A 2019, 212, 71.
doi: 10.1016/j.saa.2018.12.046
Wu, M.-X.; Sha, X.-L.; Wei, X.-R.; Sun, R.; Chen, Y.; Gao, J.; Xu, Y.-J.; Ge, J.-F. Anal. Chim. Acta 2019, 1068, 60.
doi: 10.1016/j.aca.2019.03.057
Zhong, K.; Deng, L.; Zhao, J.; Yan, X.; Sun, T.; Li, J.; Tang, L. RSC Adv. 2018, 8, 23924.
doi: 10.1039/C8RA03457E
Li, W.; Zhou, S.; Zhang, L.; Yang, Z.; Chen, H.; Chen, W.; Qin, J.; Shen, X.; Zhao, S. Sens. Actuators. B 2019, 284, 30.
doi: 10.1016/j.snb.2018.12.106
Zhang, K.; Zhang, J.; Xi, Z.; Li, L.-Y.; Gu, X.; Zhang, Q.-Z.; Yi, L. Chem. Sci. 2017, 8, 2776.
doi: 10.1039/C6SC05646F
Gong, S.; Zhou, E.; Hong, J.; Feng, G. Anal. Chem. 2019, 91, 13136.
doi: 10.1021/acs.analchem.9b03383
Cheng, H.-B.; Li, Y.; Tang, B. Z.; Yoon, J. Chem. Soc. Rev. 2020, 49, 21.
doi: 10.1039/C9CS00326F
Kim, K. H.; Singha, S.; Jun, Y. W.; Reo, Y. J.; Kim, H. R.; Ryu, H. G.; Bhunia, S.; Ahn, K. H. Chem.l Sci. 2019.
Li, X.; Li, X.; Ma, H. Chem. Sci. 2020, 11, 1617.
doi: 10.1039/C9SC05505C
Chen, J.; Wang, Z.; She, M.; Liu, M.; Zhao, Z.; Chen, X.; Liu, P.; Zhang, S.; Li, J. ACS Appl. Mater. Interfaces 2019, 11, 32605.
doi: 10.1021/acsami.9b08522
Zhong, K.; Zhou, S.; Yan, X.; Li, X.; Hou, S.; Cheng, L.; Gao, X.; Li, Y.; Tang, L. Dyes Pigm. 2020, 174, 108049.
doi: 10.1016/j.dyepig.2019.108049
Zhong, K.; Chen, L.; Pan, Y.; Yan, X.; Hou, S.; Tang, Y.; Gao, X.; Li, J.; Tang, L. Spectrochim. Acta. Part A 2019, 221, 117135.
doi: 10.1016/j.saa.2019.117135
Jin, X.; Hao, L.; She, M.; Obst, M.; Kappler, A.; Yin, B.; Liu, P.; Li, J.; Wang, L.; Shi, Z. Anal. Chim. Acta 2015, 853, 514.
doi: 10.1016/j.aca.2014.10.005
She, M.; Yang, Z.; Hao, L.; Wang, Z.; Luo, T.; Obst, M.; Liu, P.; Shen, Y.; Zhang, S.; Li, J. Sci. Reports 2016, 6, 28972.
Poronik, Y. M.; Vygranenko, K. V.; Gryko, D.; Gryko, D. T. Chem. Soc. Rev. 2019, 48, 5242.
doi: 10.1039/C9CS00166B
Yang, Z.; She, M.; Ma, S.; Yin, B.; Liu, P.; Liu, X.; Zhao, S.; Li, J. Sens. Actuators. B 2017, 242, 872.
doi: 10.1016/j.snb.2016.09.170
Jin, X.; Zhao, S.; Wang, T.; Si, L.; Liu, Y.; Zhao, C.; Zhou, H.; Leng, X.; Zhang, X. Anal. Bioanal. Chem. 2019, 411, 5985.
doi: 10.1007/s00216-019-01973-1
Gu, B.; Su, W.; Huang, L.; Wu, C.; Duan, X.; Li, Y.; Xu, H.; Huang, Z.; Li, H.; Yao, S. Sens. Actuators. B 2018, 255, 2347.
doi: 10.1016/j.snb.2017.09.045
Jin, X.; Gao, J.; Wang, T.; Feng, W.; Li, R.; Xie, P.; Si, L.; Zhou, H.; Zhang, X. Spectrochim. Acta. Part A 2020, 224, 117467.
doi: 10.1016/j.saa.2019.117467
Wang, Z.; Zhou, H.; Chen, W.; Li, Q.; Yan, B.; Jin, X.; Ma, A.; Liu, H.; Zhao, W. ACS Appl. Mater. Interfaces 2018, 10, 14045.
doi: 10.1021/acsami.8b02060
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In the first row: probe SR+H2S, Cys, Lys, GSH, NO, H2O2, OCl-, ${\rm{O}}_{\rm{2}}^ - $, SCN-, ${\rm{SO}}_{\rm{4}}^{2 - }$, ${{\rm{S}}_{\rm{2}}}{\rm{O}}_{\rm{3}}^{2 - }$, ${\rm{SO}}_{\rm{3}}^{2 - }$, Zn2+, Ca2+, Mg+, K+, Na+, ${\rm{NO}}_{\rm{3}}^ - $, CN-, I-, Br-, Cl-, ${\rm{HCO}}_{\rm{3}}^ - $. In the second row: probe SR+H2S+other ions (Cys, Lys, GSH, NO, H2O2, OCl-, ${\rm{O}}_{\rm{2}}^ - $, SCN-, ${\rm{SO}}_{\rm{4}}^{2 - }$, ${{\rm{S}}_{\rm{2}}}{\rm{O}}_{\rm{3}}^{2 - }$, ${\rm{SO}}_{\rm{3}}^{2 - }$, Zn2+, Ca2+, Mg+, K+, Na+, ${\rm{NO}}_{\rm{3}}^ - $, CN-, I-, Br-, Cl-, ${\rm{HCO}}_{\rm{3}}^ - $). λex=550 nm
The concentrations of H2S from left to right were showed as follows: 0, 1, 10, 102, 103, 104 μmol/L