Chinese Journal of Organic Chemistry >
Development of an Ultrasensitive Mitochondria-Targeted Near Infrared Fluorescent Probe for SO2 and Its Imaging in Living Cells and Mice
Received date: 2020-12-29
Revised date: 2021-02-14
Online published: 2021-02-26
Supported by
Project supported by the NSFC(21672083); Project supported by the NSFC(21877048); Project supported by the NSFC(22077048); startup fund of Guangxi University(A3040051003); Guangxi Natural Science Foundation(2019GXNSFBA245068)
Sulfur dioxide (SO2) and its derivatives (sulfites, bisulfites, etc.), as important components of active sulfur species, are closely related to the physiological processes of living organisms. In addition, excessive intake of SO2 may cause irreparable damage to the respiratory system, such as lung cancer, tracheitis, asthma, etc. Near-infrared emission fluorescent probes have strong penetrating ability and can detect biomolecules in vivoeffectively. Therefore, in this paper, a mitochondrial targeted near-infrared SO2 fluorescent probe based on the Michael addition mechanism was designed. The solution spectroscopic experiments show that XA-SO2 has significant selectivity and sensitivity to SO2, and has the ability to rapidly detect SO2. It is worth noting that XA-SO2 has good membrane permeability and has successfully detected extracellular/endogenous levels. More importantly, XA-SO2 could be enriched effectively on the mitochondria of cells, which is promising for realizing the dynamic detection of SO2 in the mitochondria of living cells.
Key words: sulfur dioxide; fluorescent probe; bioimaging; Michael addition; mitochondria
Fang Li , Yonghe Tang , Rui Guo , Weiying Lin . Development of an Ultrasensitive Mitochondria-Targeted Near Infrared Fluorescent Probe for SO2 and Its Imaging in Living Cells and Mice[J]. Chinese Journal of Organic Chemistry, 2021 , 41(3) : 1108 -1116 . DOI: 10.6023/cjoc202012049
| [1] | Sun, Y. Q.; Liu, J.; Zhang, J.; Yang, T.; Guo, W. Chem. Commun. 2013, 49, 2637. |
| [2] | Meng, Z.; Yang, Z.; Li, J.; Zhang, Q. Chemosphere 2012, 89, 579. |
| [3] | Smith, T.; Peters, J.; Reading, J.; Castle, C. Am. Rev. Respir. Dis. 1977, 116, 31. |
| [4] | Cheng, W.; Xu, J.; Guo, Z.; Yang, D.; Chen, X.; Yan, W.; Miao, P. J. Mater. Chem. B 2018, 6, 5775. |
| [5] | Kobayashi, S.; Tsuzuki, M.; Sato, N. Plant Cell Physiol. 2015, 56, 1521. |
| [6] | Beeson, W.; Abbey, D.; Knutsen, S. Environ. Health Perspect. 1998, 106, 813. |
| [7] | Zhang, Q.; Prabhu, A.; San, A.; Al-Sharab, J.; Levon, K. Biosens. Bioelectron. 2015, 72, 100. |
| [8] | Lee, W.; Teschke, K.; Kauppinen, T.; Andersen, A.; Jappinen, P.; Szadkowskastanczyk, I.; Pearce, N.; Persson, B.; Environ, A. Health Perspect. 2002, 110, 991. |
| [9] | Sang, N.; Yun, Y.; Yao, G. Y.; Li, H. Y.; Guo, L.; Li, G. K. Toxicol. Sci. 2011, 124, 400. |
| [10] | Stipanuk, M.; Ueki, I. J. Inherited Metab. Dis. 2011, 34, 17. |
| [11] | Ubuka, T.; Ohta, J.; Yao, W.; Abe, T.; Teraoka, T.; Kurozumi, Y. Amino Acids 1992, 2, 143. |
| [12] | Li, J.; Meng, Z.; Nitric Oxide, 2009, 20, 166. |
| [13] | Jin, H. F.; Wang, Y.; Wang, X. B.; Sun, Y.; Tang, C. S.; Du, J. B. Nitric Oxide 2013, 32, 561. |
| [14] | Wang, X. B.; Huang, X. M.; Ochs, T.; Li, X. Y.; Jin, H. F.; Tang, C. S.; Du, J. B. Basic Res. Cardiol. 2011, 106, 865. |
| [15] | Meng, Z.; Yang, Z.; Li, J.; Zhang, Q. Chemosphere 2012, 89, 579. |
| [16] | Wang, X. B.; Du, J. B.; Cui, H. Life Sci. 2014, 98, 63. |
| [17] | Zorov, D. B.; Isaev, N. K.; Plotnikov, E. Y.; Zorova, L. D.; Stelmashook, E. V.; Vasileva, A. K.; Arkhangelskaya, A. A.; Khrjapenkova, T. G. Biochemistry 2007, 72, 1115. |
| [18] | Du, S. X.; Jin, H. X.; Bu, D. F.; Zhao, X.; Geng, B.; Tang, C. S.; Du, J. B. Acta Pharmacol. Sin. 2008, 29, 923. |
| [19] | Xu, W.; Teoh, C. L.; Peng, J.; Su, D.; Yuan, L.; Chang, Y.-T. Biomaterials 2015, 56, 1. |
| [20] | Zhao, Y.; Qiu, W.; Yang, C.; Wang, J. Energy Fuels 2017, 31, 693. |
| [21] | Palenzuela, B.; Simonet, B.; R?′os, A.; Valcárcel, M. Anal. Chim. Acta 2005, 535, 65. |
| [22] | Daunoravicius, Z.; Padarauskas, A. Electrophoresis 2002, 23, 2439. |
| [23] | Pundir, C.; Rawal, R. Anal. Bioanal. Chem. 2013, 405, 3049. |
| [24] | Segundo, M.; Rangel, A.; Cladera, A.; Cerdá, V. Analyst 2000, 125, 1501. |
| [25] | Williams, T.; McElvany, S.; Ighodalo, E. Anal. Chim. Acta 1981, 123, 351. |
| [26] | Yue, Y. K.; Huo, F. J.; Yin, C. X. Sci. China Chem. 2017, 42, 249. (in Chinese) |
| [26] | (岳永康, 霍方俊, 阴彩霞, 中国科学: 化学, 2017, 42, 249.) |
| [27] | Zhang, S. X.; Niu, Q. M.; Wu, S. Z.; Lu, H. J.; Xing, G. W. Chin. J. Org. Chem. 2019, 39, 940. (in Chinese) |
| [27] | (张晟曦, 牛晴旻, 吴松泽, 吕海娟, 邢国文, 有机化学, 2019, 39, 940.) |
| [28] | Zhang, J. D.; Liu, A. C.; Chen, J.; Yuan, G. H.; Jin, H. Y. Prog. Chem. 2020, 32, 594. (in Chinese) |
| [28] | (张继东, 刘阿晨, 陈娇, 袁光辉, 金华峰, 化学进展, 2020, 32, 594.) |
| [29] | Zhang, L.; Li, X. A.; Gillis, K. D.; Glass, T. E. Angew. Chem. Int. Ed. 2019, 58, 7611. |
| [30] | Yue, Y. K.; Huo, F. G.; Ning, P.; Zhang, Y. B.; Chao, J. B.; Meng, X. M.; Yin, C. X. J. Am. Chem. Soc. 2017, 139, 3181. |
| [31] | Cao, D. X.; Liu, Z. Q.; Verwilst, P.; Koo, S.; Jangjili, P.; Kim, J. S.; Lin, W. Y. Chem. Rev. 2019, 119, 10403. |
| [32] | Yang, B.; Xua, J.; Zhu, H. L. Free Radical Biol. Med. 2019, 145, 42. |
| [33] | Jia, L.; Niu, L, Y.; Yang, Q, Z. Anal. Chem. 2020, 92, 10800. |
| [34] | Li, J. Z.; Sun, Y. H.; Wang, C. Y.; Cao, S. Y.; Guo, Z. Q.; Shen, Y. J.; Zhu, W. H. Anal. Chem. 2019, 91, 11946. |
| [35] | Li, T.; Huo, F. J.; Chao, J. B.; Yin, C. X. Chem. Commun. 2020, 56, 11453. |
| [36] | Chen, H.; Dong, B. L.; Tang, Y. H.; Lin, W. Y. Acc. Chem. Res. 2017, 50, 6, 1410. |
| [37] | Zhang, W. J.; Liu, T.; Huo, F. J.; Ning, P.; Wen, Y.; Meng, X. M.; Yin, C. X. Sci. China Chem. 2017, 47, 1022. (in Chinese) |
| [37] | (张伟杰, 刘涛, 霍方俊, 温莹, 孟祥明, 阴彩霞, 中国科学: 化学, 2017, 47, 1022.) |
| [38] | Zhang, W. J.; Huo, F, J.; Cheng, F, Q.; Yin, C. Y. J. Am. Chem. Soc. 2020, 142, 13, 6324. |
| [39] | Geng, L. H.; Yang, X. F.; Zhong, Y. G.; Li, Z.; Li, H. Dyes Pigm. 2015, 120, 213. |
| [40] | Huang, C, B.; Chen, H.; Li, F. Q.; An, S. Y.; Chin. J. Org. Chem. 2019, 39, 2467. (in Chinese) |
| [40] | (黄池宝, 陈会, 李福琴, 安思雅, 有机化学, 2019, 39, 2467.) |
| [41] | Yan, Y. H.; Wu, Q. R.; Che, Q. L.; Ding, M. M.; Xu, M.; Miao, J. Y.; Zhao, B. X.; Lin, Z. M. Analyst 2020, 145, 2937. |
| [42] | Zhang, W. J.; Huo, F. J.; Zhang, Y. B.; Yin, C. X. J. Mater. Chem. B 2019, 7, 1945. |
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