研究简报

一种基于半萘基罗丹明衍生物的H2S荧光探针及其应用

  • 陈卫星 ,
  • 王婷 ,
  • 张云飞 ,
  • 李淑颖 ,
  • 周宏伟 ,
  • 贾延琳 ,
  • 金洗郎
展开
  • a 西安工业大学材料与化工学院 西安 710021;
    b 中南大学材料科学与工程学院 长沙 410083

收稿日期: 2020-06-02

  修回日期: 2020-06-24

  网络出版日期: 2020-07-17

基金资助

国家自然科学基金(Nos.51603164,21807085)、陕西省自然科学基金(No.2018JQ2015)资助项目.

A Seminaphthorhodafluor-Based Fluorescent Probe for H2S Detection and Its Application

  • Chen Weixing ,
  • Wang Ting ,
  • Zhang Yunfei ,
  • Li Shuying ,
  • Zhou Hongwei ,
  • Jia Yanlin ,
  • Jin Xilang
Expand
  • a School of Material and Chemical Engineering, Xi'an Technological University, Xi'an 710021;
    b College of Materials Science and Engineering, Central South University, Changsha, 410083

Received date: 2020-06-02

  Revised date: 2020-06-24

  Online published: 2020-07-17

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 51603164, 21807085), and the Natural Science Foundation Research Project of Shaanxi Province (No. 2018JQ2015).

摘要

一种基于半萘基染料的新型比色和长波长荧光探针SR被设计与合成.该探针基于二硝基苯醚的水解反应导致独特的螺环的关-开机理.荧光强度值(635 nm)和紫外吸光度值(590 nm)与H2S的浓度(2.00~10.00 μmol/L)呈现良好的线性关系,检测限分别为0.50和1.00 μmol/L.离子干扰实验显示探针SR具有良好的抗干扰能力,并能够应用于复杂体系中的H2S检测.同时,该探针进一步应用于滤纸、凝胶和Hela细胞中H2S的快速和有效检测,该工作进一步拓宽了荧光探针对化学和环境中H2S进行检测的应用范围.

本文引用格式

陈卫星 , 王婷 , 张云飞 , 李淑颖 , 周宏伟 , 贾延琳 , 金洗郎 . 一种基于半萘基罗丹明衍生物的H2S荧光探针及其应用[J]. 有机化学, 2020 , 40(9) : 2956 -2962 . DOI: 10.6023/cjoc202006001

Abstract

A novel colorimetric and long-wavelength fluorescent probe (SR) based on seminaphthorhodafluor dye was designed and synthesized, which was used to detect H2S through the thiolysis reaction of dinitrophenyl ether and unique OFF-ON mechanism based on the spiro-ring of probe SR. The fluorescent intensity (635 nm) and absorbance (590 nm) changes exhibited an excellent linear relationship with the H2S concentration ranging from 2.00 to 10.00 μmol/L and the detection limits were 0.50 and 1.00 μmol/L, respectively. Ions interference experiments showed that probe SR had an excellent anti-interference ability and could be used to detect H2S in complex systems. The probe SR was further exploited for filter paper, hydrogel and Hela cells for the rapid and convenient detection of H2S, which extended the applications of fluorescent probes for the detection of H2S in chemistry and the environment.

参考文献

[1] Filipovic, M. R.; Zivanovic, J.; Alvarez, B.; Banerjee, R. Chem. Rev. 2018, 118, 1253.
[2] Boehning, D.; Snyder, S. H. Ann. Rev. Neurosci. 2003, 26, 105.
[3] Tang, C.; Li, X.; Du, J. Curr. Vasc. Pharmacol. 2006, 4, 17.
[4] 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.
[5] Zanardo, R. C. O.; Brancaleone, V.; Distrutti, E.; Fiorucci, S.; Cirino, G.; Wallace, J. L. FASEB J. 2006, 20, 2118.
[6] Fiorucci, S.; Antonelli, E.; Mencarelli, A.; Orlandi, S.; Renga, B.; Rizzo, G.; Distrutti, E.; Shah, V.; Morelli, A. Hepatology 2005, 42, 539.
[7] Kabil, O.; Banerjee, R. J. Biol. Chem. 2010, 285, 21903.
[8] Lefer, D. J. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 17907.
[9] Kamoun, P.; Belardinelli, M.-C.; Chabli, A.; Lallouchi, K.; Chadefaux-Vekemans, B. Am. J. Med. Genet., Part A 2003, 116A, 310.
[10] Chen, F.; Han, D.; Liu, H.; Wang, S.; Li, K.-B.; Zhang, S.; Shi, W. Analyst 2018, 143, 440.
[11] Jin, Y.; Liu, R.; Zhan, Z.; Lv, Y. Talanta 2019, 202, 159.
[12] Zong, L.; Zhang, M.; Song, Y.; Xie, Y.; Feng, J.; Li, Q.; Li, Z. Sens. Actuators. B 2018, 257, 882.
[13] Ma, C.; Wei, C.; Li, X.; Zheng, X.; Chen, B.; Wang, M.; Zhang, P.; Li, X. Dyes Pigm. 2019, 162, 624.
[14] 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.
[15] Jiao, X.; Li, Y.; Niu, J.; Xie, X.; Wang, X.; Tang, B. Anal. Chem. 2018, 90, 533.
[16] 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). (陈宇, 毕克英, 郝瑞亭, 谢萍, 黄丽娜, 王玉敏, 张俊峰, 徐锐, 吴相华, 有机化学, 2020, 40, 511.)
[17] Tang, L.; Xia, J.; Zhong, K.; Tang, Y.; Gao, X.; Li, J. Dyes Pigm. 2020, 178, 108379.
[18] He, P.; Tang, L.; Zhong, K.; Hou, S.; Yan, X. Chin. J. Org. Chem. 2017, 37, 423(in Chinese). (何平, 汤立军, 钟克利, 侯淑华, 燕小梅, 有机化学, 2017, 37, 423.)
[19] 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.
[20] Zhong, K.; Zhao, J.; Li, Q.; Hou, S.; Tang, Z.; Bian, Y.; Tang, L. Chin. J. Org. Chem. 2018, 38, 1786(in Chinese). (钟克利, 赵杰, 李秋莹, 侯淑华, 汤轶伟, 边延江, 汤立军, 有机化学, 2018, 38, 1786.)
[21] Zhao, X.-J.; Jiang, Y.-R.; Li, Y.-T.; Yang, B.-Q.; Liu, C.; Liu, Z.-H. Spectrochim. Acta. Part A 2019, 212, 71.
[22] 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.
[23] Zhong, K.; Deng, L.; Zhao, J.; Yan, X.; Sun, T.; Li, J.; Tang, L. RSC Adv. 2018, 8, 23924.
[24] Li, W.; Zhou, S.; Zhang, L.; Yang, Z.; Chen, H.; Chen, W.; Qin, J.; Shen, X.; Zhao, S. Sens. Actuators. B 2019, 284, 30.
[25] Zhang, K.; Zhang, J.; Xi, Z.; Li, L.-Y.; Gu, X.; Zhang, Q.-Z.; Yi, L. Chem. Sci. 2017, 8, 2776.
[26] Gong, S.; Zhou, E.; Hong, J.; Feng, G. Anal. Chem. 2019, 91, 13136.
[27] Cheng, H.-B.; Li, Y.; Tang, B. Z.; Yoon, J. Chem. Soc. Rev. 2020, 49, 21.
[28] 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.
[29] Li, X.; Li, X.; Ma, H. Chem. Sci. 2020, 11, 1617.
[30] 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.
[31] Zhong, K.; Zhou, S.; Yan, X.; Li, X.; Hou, S.; Cheng, L.; Gao, X.; Li, Y.; Tang, L. Dyes Pigm. 2020, 174, 108049.
[32] 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.
[33] 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.
[34] 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.
[35] Poronik, Y. M.; Vygranenko, K. V.; Gryko, D.; Gryko, D. T. Chem. Soc. Rev. 2019, 48, 5242.
[36] Yang, Z.; She, M.; Ma, S.; Yin, B.; Liu, P.; Liu, X.; Zhao, S.; Li, J. Sens. Actuators. B 2017, 242, 872.
[37] Jin, X.; Zhao, S.; Wang, T.; Si, L.; Liu, Y.; Zhao, C.; Zhou, H.; Leng, X.; Zhang, X. Anal. Bioanal. Chem. 2019, 411, 5985.
[38] 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.
[39] 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.
[40] 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.
文章导航

/

〈 〉