Citation: Hailing Zhao, Nan Li, Caixia Ma, Zhengwei Wei, Qiya Zeng, Keyi Zhang, Na Zhao, Ben Zhong Tang. An AIE probe for long-term plasma membrane imaging and membrane-targeted photodynamic therapy[J]. Chinese Chemical Letters, ;2023, 34(4): 107699. doi: 10.1016/j.cclet.2022.07.042 shu

An AIE probe for long-term plasma membrane imaging and membrane-targeted photodynamic therapy

Hailing Zhao ^a ,
Nan Li ^a ,
Caixia Ma ^a ,
Zhengwei Wei ^a ,
Qiya Zeng ^a ,
Keyi Zhang ^a ,
Na Zhao ^{a, *,} ,
Ben Zhong Tang ^b

a.
Key Laboratory of Macromolecular Science of Shaanxi Province, Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, and School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China
b.
School of Science and Engineering, Shenzhen Institute of Aggregate Science and Technology, The Chinese University of Hong Kong, Shenzhen 518172, China

nzhao@snnu.edu.cn

Received Date: 5 May 2022
Revised Date: 19 July 2022
Accepted Date: 21 July 2022
Available Online: 23 July 2022

Figures(6)

Two red-emissive luminogens (TPTH and TPTB) with typical aggregation-induced emission characteristics were developed. By introducing the heavy atom of Br at the end of alkyl chain, TPTB exhibited higher reactive oxygen species generation efficiency through both types Ⅰ and Ⅱ pathways. Due to its excellent biocompatibility and proper lipophilicity, TPTB could be used for long-term cell membrane staining and this staining ability was independent of the change of plasma membrane potential. Furthermore, TPTB could ablate the cancer cells through cell membrane-targeted photodynamic therapy.
- Aggregation-induced emission,
- Plasma membrane,
- Fluorescent probe,
- Long-term imaging,
- Photodynamic therapy
1. [1]
  M.S. Bretscher, M.C. Raff, Nature 258 (1975) 43−49. doi: 10.1038/258043a0
2. [2]
  H.E. Grecco, M. Schmick, P.I.H. Bastiaens, Cell 144 (2011) 897−907. doi: 10.1016/j.cell.2011.01.029
3. [3]
  Y. Zhang, X. Chen, C. Gueydan, J. Han, Cell Res. 28 (2018) 9−21. doi: 10.1038/cr.2017.133
4. [4]
  H. Zhu, J. Fan, J. Du, X. Peng, Acc. Chem. Res. 49 (2016) 2115−2126. doi: 10.1021/acs.accounts.6b00292
5. [5]
  P. Gao, W. Pan, N. Li, B. Tang, Chem. Sci. 10 (2019) 6035−6071. doi: 10.1039/c9sc01652j
6. [6]
  W.C.C. Tan, S.N. Nerurkar, H.Y. Cai, et al., Cancer Commun. 40 (2020) 135−153. doi: 10.1002/cac2.12023
7. [7]
  Y. Zhang, K. Park, K. Suazo, M.D. Distefano, Chem. Soc. Rev. 47 (2018) 9106−9136. doi: 10.1039/c8cs00537k
8. [8]
  L. Wang, M.S. Frei, A. Salim, K. Johnsson, J. Am. Chem. Soc. 141 (2019) 2770−2781. doi: 10.1021/jacs.8b11134
9. [9]
  H.R. Jia, Y.X. Zhu, Q.Y. Duan, F.G. Wu, Chem. Soc. Rev. 50 (2021) 6240−6277. doi: 10.1039/d1cs00067e
10. [10]
  K. Li, Y. Lyu, Y. Huang, et al., Proc. Natl. Acad. Sci. USA 118 (2021) e201803318.
11. [11]
  M.G. Honig, R.I. Hume, Trends Neurosci. 12 (1989) 333−341. doi: 10.1016/0166-2236(89)90040-4
12. [12]
  J. Mei, Y. Hong, J.W.Y. Lam, et al., Adv. Mater. 26 (2014) 5429−5479. doi: 10.1002/adma.201401356
13. [13]
  J. Mei, N.L.C. Leung, R.T.K. Kwok, J.W.Y. Lam, B.Z. Tang, Chem. Rev. 115 (2015) 11718−11940. doi: 10.1021/acs.chemrev.5b00263
14. [14]
  J. Liang, B.Z. Tang, B. Liu, Chem. Soc. Rev. 44 (2015) 2798−2811. doi: 10.1039/C4CS00444B
15. [15]
  C.W.T. Leung, Y. Hong, S. Chen, et al., J. Am. Chem. Soc. 135 (2013) 62–65. doi: 10.1021/ja310324q
16. [16]
  Y. Cui, R. Zhang, L. Yang, S. Lv, Chin. Chem. Lett. 30 (2019) 1078−1082. doi: 10.1016/j.cclet.2018.10.017
17. [17]
  Y. Li, Y. Wu, J. Chang, et al., Chem. Commun. 49 (2013) 11335−11337. doi: 10.1039/c3cc46991c
18. [18]
  G. Liu, D. Chen, L. Kong, et al., Chem. Commun. 51 (2015) 8555−8558. doi: 10.1039/C5CC02054A
19. [19]
  W. Zhang, C.Y.Y. Yu, R.T.K. Kwok, J.W.Y. Lam, B.Z. Tang, J. Mater. Chem. B 6 (2018) 1501−1507. doi: 10.1039/c7tb02947k
20. [20]
  Y. Zhang, Y. Yan, S. Xia, et al., ACS Appl. Mater. Interfaces 12 (2020) 20172–20179. doi: 10.1021/acsami.0c00903
21. [21]
  L. Shi, Y. Liu, K. Li, et al., Angew. Chem. Int. Ed. 59 (2020) 9962−9966. doi: 10.1002/anie.201909498
22. [22]
  J. Yang, J.J. Hu, J. Wei, et al. CCS Chem. 4 (2022) 464−475. doi: 10.31635/ccschem.021.202101349
23. [23]
  S.M. Sayed, H. Jia, Y. Jiang, et al., J. Mater. Chem. B 9 (2021) 4303−4308. doi: 10.1039/d1tb00049g
24. [24]
  W. Zhang, Y. Huang, Y. Chen, et al., ACS Appl. Mater. Interfaces 11 (2019) 10567–10577. doi: 10.1021/acsami.9b00643
25. [25]
  Z. Long, J. Hu, L. Yuan, et al., Nano Today 41 (2021) 101312. doi: 10.1016/j.nantod.2021.101312
26. [26]
  M. Wu, M. Gu, J. Leung, et al., Small 17 (2021) 2101770. doi: 10.1002/smll.202101770
27. [27]
  M. Wu, X.G. Liu, H. Chen, et al., Angew. Chem. Int. Ed. 60 (2021) 9093−9098. doi: 10.1002/anie.202016399
28. [28]
  J.N. Zhang, H. Kang, N. Li, et al., Chem. Sci. 8 (2017) 577−582. doi: 10.1039/C6SC02875F
29. [29]
  Z. Zhuang, J. Dai, M. Yu, et al., Chem. Sci. 11 (2020) 3405−3417. doi: 10.1039/d0sc00785d
30. [30]
  X. Hou, F. Yi, X.L. Han, et al., Chem. Eng. J. 432 (2022) 134327. doi: 10.1016/j.cej.2021.134327
31. [31]
  F.A. Villamena, E.J. Locigno, A. Rockenbauer, C.M. Hadad, J.L. Zweier, J. Phys. Chem. A 110 (2006) 13253−13258. doi: 10.1021/jp064892m
32. [32]
  H.J. Apell, Curr. Opin. Cell Biol. 2 (1990) 708−713. doi: 10.1016/0955-0674(90)90114-T
1. [1]
  Xuejian Xing , Pan Zhu , E Pang , Shaojing Zhao , Yu Tang , Zheyu Hu , Quchang Ouyang , Minhuan Lan . D-A-D-structured boron-dipyrromethene with aggregation-induced enhanced phototherapeutic efficiency for near-infrared fluorescent and photoacoustic imaging-guided synergistic photodynamic and photothermal cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109452-. doi: 10.1016/j.cclet.2023.109452
2. [2]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
3. [3]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
4. [4]
  Leichen Wang , Anqing Mei , Na Li , Xiaohong Ruan , Xu Sun , Yu Cai , Jinjun Shao , Xiaochen Dong . Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy. Chinese Chemical Letters, 2024, 35(6): 108974-. doi: 10.1016/j.cclet.2023.108974
5. [5]
  Jun-Jie Fang , Zheng Liu , Yun-Peng Xie , Xing Lu . Superatomic Ag₅₈ nanoclusters incorporating a [MS₄@Ag₁₂]²⁺ (M = Mo or W) kernel show aggregation-induced emission. Chinese Chemical Letters, 2024, 35(10): 109345-. doi: 10.1016/j.cclet.2023.109345
6. [6]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
7. [7]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
8. [8]
  Lei Shen , Hongmei Liu , Ming Jin , Jinchao Zhang , Caixia Yin , Shuxiang Wang , Yutao Yang . “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone. Chinese Chemical Letters, 2024, 35(10): 109572-. doi: 10.1016/j.cclet.2024.109572
9. [9]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
10. [10]
  Yu Qin , Mingyang Huang , Chenlu Huang , Hannah L. Perry , Linhua Zhang , Dunwan Zhu . O₂-generating multifunctional polymeric micelles for highly efficient and selective photodynamic-photothermal therapy in melanoma. Chinese Chemical Letters, 2024, 35(7): 109171-. doi: 10.1016/j.cclet.2023.109171
11. [11]
  Hao Cai , Xiaoyan Wu , Lei Jiang , Feng Yu , Yuxiang Yang , Yan Li , Xian Zhang , Jian Liu , Zijian Li , Hong Bi . Lysosome-targeted carbon dots with a light-controlled nitric oxide releasing property for enhanced photodynamic therapy. Chinese Chemical Letters, 2024, 35(4): 108946-. doi: 10.1016/j.cclet.2023.108946
12. [12]
  Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
13. [13]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
14. [14]
  Jiajia Lv , Jie Gao , Hongyu Li , Zeli Yuan , Nan Dong . Rational design of hydroxytricyanopyrrole-based probes with high affinity and rapid visualization for amyloid-β aggregates in vitro and in vivo. Chinese Chemical Letters, 2024, 35(5): 108940-. doi: 10.1016/j.cclet.2023.108940
15. [15]
  Kun-Heng Li , Hong-Yang Zhao , Dan-Dan Wang , Ming-Hui Qi , Zi-Jian Xu , Jia-Mi Li , Zhi-Li Zhang , Shi-Wen Huang . Mitochondria-targeted nano-AIEgens as a powerful inducer for evoking immunogenic cell death. Chinese Chemical Letters, 2024, 35(5): 108882-. doi: 10.1016/j.cclet.2023.108882
16. [16]
  Xinyue Lan , Junguang Liang , Churan Wen , Xiaolong Quan , Huimin Lin , Qinqin Xu , Peixian Chen , Guangyu Yao , Dan Zhou , Meng Yu . Photo-manipulated polyunsaturated fatty acid-doped liposomal hydrogel for flexible photoimmunotherapy. Chinese Chemical Letters, 2024, 35(4): 108616-. doi: 10.1016/j.cclet.2023.108616
17. [17]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
18. [18]
  Jinyu Guo , Yandai Lin , Shaohua He , Yueqing Chen , Fenglu Li , Renjie Ruan , Gaoxing Pan , Hexin Nan , Jibin Song , Jin Zhang . Utilizing dual-responsive iridium(Ⅲ) complex for hepatocellular carcinoma: Integrating photoacoustic imaging with chemotherapy and photodynamic therapy. Chinese Chemical Letters, 2024, 35(9): 109537-. doi: 10.1016/j.cclet.2024.109537
19. [19]
  Fengkai Zou , Borui Su , Han Leng , Nini Xin , Shichao Jiang , Dan Wei , Mei Yang , Youhua Wang , Hongsong Fan . Red-emissive carbon quantum dots minimize phototoxicity for rapid and long-term lipid droplet monitoring. Chinese Chemical Letters, 2024, 35(10): 109523-. doi: 10.1016/j.cclet.2024.109523
20. [20]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(262)
HTML views(36)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142