Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2535-2541.DOI: 10.6023/cjoc202202037 Previous Articles     Next Articles



夏伟康a,b, 刘闯c, 叶盛c, 汪磊a,b,*(), 刘瑞源c,*()   

  1. a 三峡大学材料与化工学院 湖北宜昌 443002
    b 湖北省三峡实验室 湖北宜昌 443007
    c 南方医科大学生物医学工程学院 广州 510515
  • 收稿日期:2022-02-28 修回日期:2022-04-18 发布日期:2022-05-06
  • 通讯作者: 汪磊, 刘瑞源
  • 基金资助:

Synthesis of A Sulfonamide-Substituted Benzothiadiazole-Based Fluorescent Dye and Study of Its Application for Long-Term Cancer Cell Tracking

Weikang Xiaa,b, Chuang Liuc, Sheng Yec, Lei Wanga,b(), Ruiyuan Liuc()   

  1. a College of Materials and Chemical Engineering, China Three Gorges University, Yichang, Hubei 443002
    b Hubei Three Gorges Laboratory, Yichang, Hubei 443007
    c School of Biomedical Engineering, Southern Medical University, Guangzhou, 510515
  • Received:2022-02-28 Revised:2022-04-18 Published:2022-05-06
  • Contact: Lei Wang, Ruiyuan Liu
  • 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.

Key words: long-term cancer cell tracking, benzothiadiazole, N,N-dimethyl substituted sulfonamide, aggregation-induced emission