Chinese Journal of Organic Chemistry >
Synthesis of A Sulfonamide-Substituted Benzothiadiazole-Based Fluorescent Dye and Study of Its Application for Long-Term Cancer Cell Tracking
Received date: 2022-02-28
Revised date: 2022-04-18
Online published: 2022-05-07
Supported by
111 Project of Hubei Province(2018-19-1)
To develop long-term cancer cell tracking dyes with anti-photobleaching, large Stokes shift, and excellent biocompatibility is the research hotspot in the field of biological imaging. In this study, a donor-acceptor-donor (D-A-D) stuctured benzothiadiazole (BTD)-based fluorescent dye was sythesized, namely SIBIS. The BTD with excellent optical properties was chosen as the core stucture and the N,N-dimethyl substituted sulfonamide was selceted to improve the biocompatibility and solubility of fluorescent dye. SIBIS possessed aggregation-induced emission (AIE), large Stokes shift (155 nm) and low cytotoxicity. The endocytosis results in different cell lines showed that SIBIS could target lysosome of living cells. The long-term 4T1 cell tracking results showed that SIBIS could effectively trace cell divisions for more than 15 generations. Therefore, SIBIS can serve as a kind of promising long-term cell traking agents tumor cells, and has a great potential for further biological applications for tracking various kinds of lysosomal related inflammation and diseases.
Weikang Xia , Chuang Liu , Sheng Ye , Lei Wang , Ruiyuan Liu . Synthesis of A Sulfonamide-Substituted Benzothiadiazole-Based Fluorescent Dye and Study of Its Application for Long-Term Cancer Cell Tracking[J]. Chinese Journal of Organic Chemistry, 2022 , 42(8) : 2535 -2541 . DOI: 10.6023/cjoc202202037
| [1] | Siegel, R. L.; Miller, K. D.; Fuchs, H. E.; Jemal, A. Ca-Cancer J. Clin. 2021, 71, 7. |
| [2] | Shi, J.; Kantoff, P. W.; Wooster, R.; Farokhzad, O. C. Nat. Rev. Cancer 2017, 17, 20. |
| [3] | Dhanasekaran, R.; Deutzmann, A.; Mahauad-Fernandez, W. D.; Hansen, A. S.; Gouw, A. M.; Felsher, D. W. Nat. Rev. Clin. Oncol. 2022, 19, 23. |
| [4] | Blanpain, C. Nat. Cell Biol. 2013, 15, 126. |
| [5] | Chen, Z.; Li, J.; Chen, X.; Cao, J.; Zhang, J.; Min, Q.; Zhu, J. J. J. Am. Chem. Soc. 2015, 137, 1903. |
| [6] | Ning, X.; Bao, H.; Liu, X.; Fu, H.; Wang, W.; Huang, J.; Zhang, Z. Nanoscale 2019, 11, 20932. |
| [7] | Das, B.; Girigoswami, A.; Pal, P.; Dhara, S. Mater. Sci. Eng.,C 2019, 102, 427. |
| [8] | Song, L.; Lin, X. H.; Song, X. R.; Chen, S.; Chen, X. F.; Li, J.; Yang, H. H. Nanoscale 2017, 9, 2718. |
| [9] | Ma, H.; Hu, D.; Zhao, J.; Tian, M.; Yuan, J.; Wei, Y. CCS Chem. 2021, 3, 1569. |
| [10] | Wang, Z. L.; Qiao, R. R.; Tang, N.; Lu, Z. W.; Wang, H.; Zhang, Z. X.; Xue, X. D.; Huang, Z. Y.; Zhang, S. R.; Zhang, G. X.; Li, Y. P. Biomaterials 2017, 127, 25. |
| [11] | Kikuchi, K. Chem. Soc. Rev. 2010, 39, 2048. |
| [12] | Geng, X.; Sun, Y.; Li, Z.; Yang, R.; Zhao, Y.; Guo, Y.; Xu, J.; Li, F.; Wang, Y.; Lu. S.; Qu, L. Small 2019, 15, 1901517. |
| [13] | Chen, X.; Zhang, X.; Xia, L. Y.; Wang, H. Y.; Chen, Z.; Wu, F. G. Nano Lett. 2018, 18, 1159. |
| [14] | Yang, Z.; Wang, X.; Liang, G.; Yang, A.; Li, J. J. Mater. Chem. B 2022, 10, 518. |
| [15] | Andreiuk, B.; Reisch, A.; Lindecker, M.; Follain, G.; Peyriéras, N.; Goetz, J. G.; Klymchenko, A. S. Small 2017, 13, 1701582. |
| [16] | Xia, Q.; Chen, Z. K.; Zhang, Z. D.; Liu, R. Y. Chin. J. Org. Chem. 2018, 38, 2700. (in Chinese) |
| [16] | (夏琦, 陈子康, 张志德, 刘瑞源, 有机化学, 2018, 38, 2700.) |
| [17] | Li, D.; Qin, W.; Xu, B.; Qian, J.; Tang, B. Z. Adv. Mater. 2017, 29, 1703643. |
| [18] | Yong, K.-T.; Law, W.-C.; Hu, R.; Ye, L.; Liu, L.; Swihart, M. T.; Prasad, P. N. Chem. Soc. Rev. 2013, 42, 1236. |
| [19] | Kaur, P.; Singh, K. J. Mater. Chem. C 2019, 7, 11361. |
| [20] | Xie, J.; Wang, L.; Su, X.; Rodrigues, J. Curr. Org. Chem. 2021, 25, 2142. |
| [21] | Yu, H. X.; Zhi, J.; Chang, Z. F.; Shen, T.; Ding, W. L.; Zhang, X.; Wang, J. L. Mater. Chem. Front. 2019, 3, 151. |
| [22] | Li, Y.; Zhou, Y.; Yue, X.; Dai, Z. Adv. Healthcare Mater. 2020, 9, 2001327. |
| [23] | Yu, C. J.; Guo, X.; Fang, X. B.; Chen, N.; Wu, Q. H.; Hao, E. H.; Jiao, L. J. Dyes Pigm. 2022, 197, 109838. |
| [24] | Yu, C. J.; Fang, X. B.; Wang, H.; Guo, X.; Sun, L. L.; Wu, Q. H.; Jiao, L. J.; Hao, E. H. J. Org. Chem. 2021, 86, 11492. |
| [25] | Guo, X.; Tang, B.; Wu, H.; Wu, Q. H.; Xie, Z.Y.; Yu, C. J.; Hao, E. H.; Jiao, L. J. Mater. Chem. Front. 2021, 5, 3664. |
| [26] | Shi, Z. X.; Han, X.; Hu, W. B.; Bai, H.; Peng, B.; Ji, L.; Fan, Q. L.; Li, L.; Huang, W. Chem. Soc. Rev. 2020, 49, 7533. |
| [27] | Fan, G. W.; Wang, N. N.; Zhang, J.; Ji, X.; Qi, S. C.; Tao, Y. F.; Zhao, W. L. Dyes Pigm. 2022, 199, 110073. |
| [28] | Pham, T. C.; Nguyen, V. N.; Choi, Y.; Lee, S.; Yoon, J. Chem. Rev. 2021, 121, 13454. |
| [29] | Chi, C. Y.; Mikhailovsky, A.; Bazan, G. C. J. Am. Chem. Soc. 2007, 129, 11134. |
| [30] | Neto, B. A.; Carvalho, P. H.; Correa, J. R. Acc. Chem. Res. 2015, 48, 1560. |
| [31] | Yao, H.; Dai, J.; Zhuang, Z.; Yao, J.; Wu, Z.; Wang, S.; Xia, F.; Zhou, J.; Lou, X. D.; Zhao, Z. Z. Sci. China: Chem. 2020, 63, 1815. |
| [32] | Wang, L.; Xia, Q.; Hou, M. R.; Yan, C. G.; Xu, Y.; Qu, J. Q.; Liu, R. R. J. Mater. Chem. B 2017, 5, 9183. |
| [33] | Liu, J.; Li, K.; Liu, B. Adv. Sci. 2015, 2, 1500008. |
| [34] | Qin, W.; Li, K.; Feng, G.; Li, M.; Yang, Z.; Liu, B.; Tang, B. Z. Adv. Funct. Mater. 2014, 24, 635. |
| [35] | Bujacz, G.; Alexandratos, J.; Wlodawer, A.; Merkel, G.; Andrake, M.; Katz, R. A.; Skalka, A. M. J. Biol. Chem. 1997, 272, 18161. |
| [36] | Tamura, T.; Ueda, T.; Goto, T.; Tsukidate, T.; Shapira, Y.; Nishikawa, Y.; Fujisawa, A.; Hamachi, I. Nat. Commun. 2018, 9, 1870. |
| [37] | Wang, L.; Tran, M.; D’Este, E.; Roberti, J.; Koch, B.; Xue, L.; Johnsson, K. Nat. Chem. 2020, 12, 165. |
| [38] | Gao, S.; Yu, S.; Zhang, Y.; Wu, A.; Zhang, S.; Wei, G.; Wang, H.; Xiao, Z.; Lu, W. Adv. Funct. Mater. 2021, 31, 2008356. |
| [39] | Yang, Z.; Zhang, Z.; Sun, Y.; Lei, Z.; Wang, D.; Ma, H.; Tang, B. Z. Biomaterials 2021, 275, 120934. |
| [40] | Tian, X. Q.; Zuo, M. Z.; Niu, P. B.; Wang, K. Y.; Hu, X. Y. Chin. J. Org. Chem. 2020, 40, 1823. (in Chinese) |
| [40] | (田雪琪, 左旻瓒, 牛蓬勃, 王开亚, 胡晓玉, 有机化学, 2020, 40, 1823.) |
| [41] | Wang, L. F.; Qian, Y. Chin. J. Org. Chem. 2020, 40, 1246. (in Chinese) |
| [41] | (王凌锋, 钱鹰, 有机化学, 2020, 40, 1246.) |
| [42] | Bock, L.; Miller, G. H.; Schaper, K. -J.; Seydel, J. K. J. Med. Chem. 1974, 17, 23. |
| [43] | Rousseau, J. F.; Dodd, R. H. Heterocycles 2001, 55, 2289. |
/
| 〈 |
|
〉 |
