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2021 , Vol. 41 >Issue 3: 1200 - 1206

DOI: https://doi.org/10.6023/cjoc202009016

研究论文

基于硝基还原机理的一氧化碳荧光探针的开发及细胞成像研究

  • 陈恩庆 ,
  • 唐永和 ,
  • 王蕾 ,
  • 任江波 ,
  • 林伟英
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  • a 广西电化学能源材料重点实验室 广西大学光功能材料与化学生物学研究院 广西大学化学化工学院 南宁 530004
    b 南宁市食品药品检验所 南宁 530007

收稿日期: 2020-09-07

  修回日期: 2020-10-06

  网络出版日期: 2020-10-28

基金资助

国家自然科学基金(21672083); 国家自然科学基金(21877048); 国家自然科学基金(22077048); 广西大学启动基金(A3040051003); 广西省自然科学基金(2019GXNSFBA245068)

收起

Development of a New Carbon Monoxide Fluorescent Probe Based on Nitro Reduction and Its Bioimaging Research in Living Cells

  • Enqing Chen ,
  • Yonghe Tang ,
  • Lei Wang ,
  • Jiangbo Ren ,
  • Weiying Lin
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  • a Guangxi Key Laboratory of Electrochemical Energy Materials, Institute of Optical Materials and Chemical Biology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004
    b Nanning Institute for Food and Drug Control, Nanning 530007
* Corresponding author. E-mail:

Received date: 2020-09-07

  Revised date: 2020-10-06

  Online published: 2020-10-28

Supported by

National Natural Science Foundation of China(21672083); National Natural Science Foundation of China(21877048); National Natural Science Foundation of China(22077048); Startup Fund of Guangxi University(A3040051003); Natural Science Foundation of Guangxi Province(2019GXNSFBA245068)

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摘要

一氧化碳(CO)作为一种重要的细胞气体信号传递分子, 参与生物体内重要的生理和病理功能. 选用经典的荧光平台——萘酰亚胺荧光平台, 以硝基基团作为识别位点, 通过严谨的设计和两步合成的方法, 开发了一种新型用来检测一氧化碳的荧光增强型荧光探针NaLy-CO. 光谱测试数据表明, 该荧光探针对一氧化碳具有较好的选择性和灵敏度. 利用荧光共聚焦成像技术, 成功地对细胞外源性和内源性一氧化碳进行了检测. 此外, 共定位成像实验表明, 该荧光探针可以用于检测细胞溶酶体中的一氧化碳.

关键词： 一氧化碳; 荧光探针; 生物成像; 硝基; 萘酰亚胺

本文引用格式

陈恩庆 , 唐永和 , 王蕾 , 任江波 , 林伟英 . 基于硝基还原机理的一氧化碳荧光探针的开发及细胞成像研究[J]. 有机化学, 2021 , 41(3) : 1200 -1206 . DOI: 10.6023/cjoc202009016

Abstract

Carbon monoxide (CO), as an important cell signaling molecule, is involved in important physiological and pathological functions in organism. A new fluorescence enhanced CO fluorescent probe NaLy-CO was developed by using naphthalimide dye as fluorescence platform and nitro group as the recognition site. The results of spectrum test in solution showed that the fluorescent probe NaLy-CO had good selectivity and sensitivity to CO. The fluorescent probe NaLy-CO was successfully used to detect exogenous and endogenous CO in living HeLa cells by using confocal fluorescence imaging technology. In addition, the colocation imaging experiments showed that the fluorescent probe NaLy-CO could detect CO in the lysosome of living cells.

Key words： carbon monoxide; fluorescent probe; bioimaging; nitro; naphthalimide

参考文献

[1]
Prockop, L. D.; Chichkova, R. I. J. Neurol. Sci. 2007, 262, 122.
[2]
Sjostrand, T. J. Clin. Invest. 1949, 28, 201.
[3]
Brune, B.; Ullrich, V. Mol. Pharmacol. 1987, 32, 497.
[4]
Prabhakar, N. R.; Dinerman, J. L.; Agani, F. H.; Snyder, S. H. Proc. Natl. Acad. Sci. U. S. A. 1995, 92, 1994.
[5]
Paro, F. M.; Steiner, A. A.; Branco, L. G. S. J. Therm. Biol. 2001, 26, 339.
[6]
Sato, K.; Balla, J.; Otterbein, L.; Smith, R. N.; Brouard, S.; Lin, Y.; Csizmadia, E.; Sevigny, J.; Robson, S. C.; Vercellotti, G.; Choi, A. M.; Bach, F. H.; Soares, M. P. J. Immunol. 2001, 166, 4185.
[7]
Foresti, R.; Motterlini, R. Free Radical Res. 1999, 31, 459.
[8]
Heinemann, S. H.; Hoshi, T.; Westerhausen, M.; Schiller, A. Chem. Commun. 2014, 50, 3644.
[9]
Lee, I. T.; Luo, S.-F.; Lee, C.-W.; Wang, S.-W.; Lin, C.-C.; Chang, C.-C.; Chen, Y.-L.; Chau, L.-Y.; Yang, C.-M. Am. J. Pathol. 2009, 175, 519.
[10]
Ryter, S. W.; Choi, A. M. K. Transl. Res. 2016, 167, 7.
[11]
Wu, L.; Wang, R. Pharmacol. Rev. 2005, 57, 585.
[12]
Schroeder, R. A.; Ewing, C. A.; Sitzmann, J. V.; Kuo, P. C. Dig. Dis. Sci. 2000, 45, 2405.
[13]
Watts, C. Biochim. Biophys. Acta, Proteins Proteomics 2012, 1824, 14.
[14]
Zhao, H. Traffic 2012, 13, 1307.
[15]
Li, M.; Wang, Y.; Liu, G.; Lü, H.; Xing, G. Chin. J. Org. Chem., 2017, 37, 356. (in Chinese)
[15]
(李美含, 王宇童, 刘广建, 吕海娟, 邢国文, 有机化学, 2017, 37, 356.)
[16]
Dell'Angelica, E. C. FASEB J. 2000, 14, 1265.
[17]
Benito-Garagorri, D.; Puchberger, M.; Mereiter, K.; Kirchner, K. Angew. Chem., Int. Ed. 2008, 47, 9142.
[18]
Kitagishi, H.; Minegishi, S.; Yumura, A.; Negi, S.; Taketani, S.; Amagase, Y.; Mizukawa, Y.; Urushidani, T.; Sugiura, Y.; Kano, K. J. Am. Chem. Soc. 2016, 138, 5417.
[19]
Park, S. S.; Kim, J.; Lee, Y. Anal. Chem. 2012, 84, 1792.
[20]
Lv, B.; Xu, X.; Huang, D.; Wu, P.; Sheng, Z.; Liu, W.; Li, D.; Alharbi, N. S.; Zhang, K.; Wang, S. Chin. J. Org. Chem. 2018, 38, 3165. (in Chinese)
[20]
(吕卉, 徐学涛, 黄丹颖, 吴盼盼, 盛钊君, 刘文锋, 李冬利, Alharbi, N. S., 张焜, 王少华, 有机化学, 2018, 38, 3165.)
[21]
Li, Y.; Lü, Z.; Liu, M.; Xing, G. Chin. J. Org. Chem. 2016, 36, 962. (in Chinese)
[21]
(李杨洁, 吕子奇, 刘敏, 邢国文, 有机化学, 2016, 36, 962.)
[22]
Luo, X.; Chen, M.; Yang, Q. Acta Chim. Sinica 2020, 78, 373. (in Chinese)
[22]
(罗兴蕊, 陈敏文, 杨晴来, 化学学报, 2020, 78, 373.)
[23]
Wei, C.; Zhang, P.; Li, X. Chin. J. Org. Chem. 2019, 39, 3375. (in Chinese)
[23]
(魏超, 张平竹, 李小六, 有机化学, 2019, 39, 3375.)
[24]
Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996, 96, 2035.
[25]
Wang, K.-R.; Qian, F.; Wang, X.-M.; Tan, G.-H.; Rong, R.-X.; Cao, Z.-R.; Chen, H.; Zhang, P.-Z.; Li, X.-L. Chin. Chem. Lett. 2014, 25, 1087.
[26]
Ma, C.; Wei, C.; Li, X.; Zheng, X.; Chen, B.; Wang, M.; Zhang, P.; Li, X. Dyes Pigm. 2019, 162, 624.
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