journal article·2019-03-20

Amphiphilic Tetraphenylethene-Based Pyridinium Salt for Selective Cell-Membrane Imaging and Room-Light-Induced Special Reactive Oxygen Species Generation

Weijie Zhang, Yuhua Huang, Yilong Chen, Engui Zhao, Yuning Hong, Sijie Chen, Jacky W. Y. Lam, Yuncong Chen, Jianquan Hou, Ben Zhong Tang

ACS Applied Materials & Interfaces· Volume 11· Issue 11
Publisher page

Abstract

The cell membrane is the protecting frontier of cells, which is crucial for maintaining cell integrity, and has a close relationship with cell growth and death. There is a growing need for cell membrane imaging and monitoring in both living and dying cells. Herein, we report a new amphiphilic tetraphenylethene-based pyridinium salt (TPE-MEM) with aggregation-induced emission features for discriminatory cell membrane imaging. The fluorogenic probe with high yield was synthesized following asymmetric McMurry reaction, Williamson ether synthesis reaction, Suzuki coupling, and aldol condensation between a double-charged pyridinium salt and hexyloxytetraphenylethene benzaldehyde. TPE-MEM shows good water solubility, biocompatibility, and cell membrane specificity. Interestingly, a reactive oxygen species (ROS) is produced by the molecule (TPE-MEM) under room-light irradiation, which could destroy the integrity of the plasma membrane and cause cell necrosis. This enables a visible observation of cell necrosis and the phototherapeutic effect under a mild condition. Preliminary animal investigations also demonstrated the photodynamic therapy (PDT) effectiveness of TPE-MEM in tumor growth inhibition. We conclude that TPE-MEM is potentially a cell membrane-selective photosensitizer for PDT and it is worthy of further exploration of the phototherapeutic effect on animals systematically.
Source: openalex_inverted_index · Quality: baseline

Research context

OpenAlex topics: Luminescence and Fluorescent Materials · Nanoplatforms for cancer theranostics · Molecular Sensors and Ion Detection

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Urology, The First Affiliated Hospital of Soochow University, 188 Shizi RD, Suzhou 215006, China

HKUST Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park Nanshan, Shenzhen 518057, China

Department of Chemistry, The Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction and Institute for Advanced Study, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China

School of Chemical Engineering and Energy Technology, Dongguan University of Technology, 1st University Road, Songshan Lake District, Dongguan 523808, China

Department of Chemistry and Physics, La Trobe Institute of Molecular Science, La Trobe University, Melbourne, Victoria, Australia 2086

Center for Aggregation-Induced Emission, SCUT-HKUST Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China

Funding

National Natural Science Foundation of China · Research Grants Council, University Grants Committee · Innovation and Technology Commission · Government of Jiangsu Province · Science and Technology Plan of Shenzhen

References (48)

Show source-provided references
1. 10.1038/nrc107110.1038/nrc1071 ↗
2. 10.1021/cr900236h10.1021/cr900236h ↗
3. 10.3322/caac.2011410.3322/caac.20114 ↗
4. 10.1021/cr900300p10.1021/cr900300p ↗
5. 10.3390/cancers302251610.3390/cancers3022516 ↗
6. 10.1054/bjoc.2001.179510.1054/bjoc.2001.1795 ↗
7. 10.2307/357981610.2307/3579816 ↗
8. 10.1016/j.bbcan.2007.07.00110.1016/j.bbcan.2007.07.001 ↗
9. 10.1039/B700350A10.1039/B700350A ↗
10. 10.1111/j.1751-1097.1997.tb03176.x10.1111/j.1751-1097.1997.tb03176.x ↗
11. 10.1111/j.1751-1097.1991.tb03669.x10.1111/j.1751-1097.1991.tb03669.x ↗
12. 10.1039/B108586G10.1039/B108586G ↗
13. 10.1111/j.1751-1097.1997.tb08581.x10.1111/j.1751-1097.1997.tb08581.x ↗
14. 10.1002/jcp.1027310.1002/jcp.10273 ↗
15. Fabris C. · Cancer Res. · 2001 · 61 · 7495
16. 10.1039/b206046a10.1039/b206046a ↗
17. Johnson I. · 2010
18. 10.1021/jo800852h10.1021/jo800852h ↗
19. 10.1039/B105159H10.1039/B105159H ↗
20. 10.1039/B904665H10.1039/B904665H ↗
21. 10.1039/c1cs15113d10.1039/c1cs15113d ↗
22. 10.1039/c0jm04449k10.1039/c0jm04449k ↗
23. 10.1039/c2jm31482g10.1039/c2jm31482g ↗
24. 10.1039/C1JM14054J10.1039/C1JM14054J ↗
25. 10.1039/c3tc30759j10.1039/c3tc30759j ↗
26. 10.1021/ar300346410.1021/ar3003464 ↗
27. 10.1021/ja310324q10.1021/ja310324q ↗
28. 10.1002/chem.20090250510.1002/chem.200902505 ↗
29. 10.1021/jp073147m10.1021/jp073147m ↗
30. 10.1021/ac101802810.1021/ac1018028 ↗
31. 10.1002/chem.20090077810.1002/chem.200900778 ↗
32. 10.1002/adma.20110171410.1002/adma.201101714 ↗
33. 10.1038/srep0115010.1038/srep01150 ↗
34. 10.1002/marc.20120076010.1002/marc.201200760 ↗
35. 10.1039/c2sc01108e10.1039/c2sc01108e ↗
36. 10.1021/ja400337p10.1021/ja400337p ↗
37. 10.1039/C3TB21675F10.1039/C3TB21675F ↗
38. 10.1002/adhm.20120047510.1002/adhm.201200475 ↗
39. 10.1039/c3cc46991c10.1039/c3cc46991c ↗
40. 10.1002/chem.20070172310.1002/chem.200701723 ↗
41. 10.1055/s-2007-96590610.1055/s-2007-965906 ↗
42. Alberts B. · 2002
43. Lodish H. · 2012
44. 10.2174/138945005454596210.2174/1389450054545962 ↗
45. 10.1016/S1572-1000(05)00110-910.1016/S1572-1000(05)00110-9 ↗
46. 10.1021/tx00026a01210.1021/tx00026a012 ↗
47. 10.1016/S0008-6363(99)00384-310.1016/S0008-6363(99)00384-3 ↗
48. 10.1038/3508500810.1038/35085008 ↗