Design of High Efficiency Cationic Photosensitizer and Its Application in Low Irradiation Dose Photodynamic Antibacterial

doi:10.6023/cjoc202503024

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (11): 4143-4151.DOI: 10.6023/cjoc202503024 Previous Articles Next Articles

ARTICLES

高效率阳离子型光敏剂的设计及其在低辐照剂量光动力抗菌中应用

白雪^a, 谢祎黎^b, 李君缘^a, 莫梓华^a, 万清^a^,^c^,^*()

^a 南昌航空大学材料科学与工程学院南昌 330036
^b 豫章师范学院生态与环境学院南昌 330103
^c 华南理工大学聚集诱导发光高等研究院广州 510530

收稿日期:2025-03-24 修回日期:2025-06-07 发布日期:2025-08-18
基金资助:
国家自然科学基金(52303233); 中国科协青年人才托举(2023QNRC001); 江西省自然科学基金(20224BAB214001); 江西省自然科学基金(20232BAB203026); 广东省基础与应用基础研究基金(2023A1515110186)

Design of High Efficiency Cationic Photosensitizer and Its Application in Low Irradiation Dose Photodynamic Antibacterial

Xue Bai^a, Yili Xie^b, Junyuan Li^a, Zihua Mo^a, Qing Wan^a^,^c^,^*()

^a School of Materials Science and Engineering, Nanchang Hangkong University, Nanchang 330063
^b School of Ecology and Environment, Yuzhang Normal University, Nanchang 330103
^c Aggregation-Induced Emission (AIE) Institute, South China University of Technology, Guangzhou 510530

Received:2025-03-24 Revised:2025-06-07 Published:2025-08-18
Contact: *E-mail: wanqingwork@nchu.edu.cn
Supported by:
National Natural Science Foundation of China(52303233); Young Elite Scientists Sponsorship Program by the China Association for Science and Technology(2023QNRC001); Natural Science Foundation of Jiangxi Province(20224BAB214001); Natural Science Foundation of Jiangxi Province(20232BAB203026); Guangdong Basic and Applied Basic Research Foundation(2023A1515110186)

1. .pdf(1826KB)

Abstract

Fluorescent image-guided photodynamic therapy (PDT) has many advantages such as in situ visualization, precision treatment, easy operation, and no drug resistance, which has shown important application potential in the imaging and treatment of cancer cells and drug-resistant bacteria. Photosensitizer (PS) is an important part of PDT, and its fluorescence and reactive oxygen species (ROS) efficiency directly affect phototherapeutic effect. Traditional methods mainly enhance the intramolecular charge transfer or introduction of the heavy atom effect to promote the intersystem crossing (ISC) process to produce more triplet energy, but seriously quenching the fluorescent efficiency of the PS. Therefore, it is important to develop molecular engineering that can improve simultaneously the fluorescence and ROS efficiency of PS. This work reports a strategy to improve the molecular molar absorption coefficient by introducing fusing ring units with different rigidity between the electronic donor and acceptor, which not only improves the photoluminescence quantum efficiency, but also greatly improving the efficiency of producing type I/II ROS. Using triphenylamine as electronic donor and cationic pyridine as acceptor, three cationic PSs (TPA-B-PI, TPA-N-PI and TPA-Py-PI) with different molar absorption coefficients were designed and prepared by introducing benzene, naphthalene and pyrene rings between electronic donor and acceptor. The photophysical and photo-sensitive properties of the PSs were researched in detail. Experimental results showed that, owing to the larger absorption cross section of pyrene molecule, TPA-Py-PI exhibited a superior molar absorption coefficient. Furthermore, more singlet and triplet excitons were generated after excitation, resulting in the best fluorescence quantum efficiency and type I/II ROS efficiency. The results of photodynamic antibacterial experiment showed that the TPA-Py-PI had good antibacterial effect on Staphylococcus aureus (S. aureus), drug-resistant Staphylococcus aureus (MRSA) and Escherichia coli (E. coli). Moreover, TPA-Py-PI achieved good antibacterial efficiency of 99.99% against MRSA at low concentration (25 nmol/L) and irradiation dose (20 mW/cm²).

Key words: photodynamic therapy, cationic photosensitizer, molar absorbance coefficient, antibacterial

Cite this article

Xue Bai, Yili Xie, Junyuan Li, Zihua Mo, Qing Wan. Design of High Efficiency Cationic Photosensitizer and Its Application in Low Irradiation Dose Photodynamic Antibacterial[J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 4143-4151.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

Scheme 1. Synthestic route of compound TPA-B-PI, TPA-N-PI, and TPA-Py-PI

Figure 1. Electronic distribution of HOMOs and LUMOs of TPA-B-PI, TPA-N-PI and TPA-Py-PI calculated by using the MX-062/6-31G (d,p) basis set

Figure 2. (A) UV-Vis absorption, (B) PL spectra and (C) normalized PL spectra of TPA-B-PI, TPA-N-PI and TPA-Py-PI in THF Concentration of PS: 10 μmol/L

Figure 3. (A) Change of absorption intensity of ABDA probe in PSs-contained DMSO/H2O mixture; (B) Change of fluorescence intensity of DHR123 probe and (C) HPF probe in PSs-contained DMSO/H2O mixture Concentration of PS: 10 μmol/L, concentration of ABDA: 20 μmol/L, concentration of DHR123: 5 μmol/L, concentration of HPF: 5 μmol/L, DMSO/H2O (V/V=1/99), white light power: 30 mW/cm2

Figure 4. After the action with or without white light irradiation by the plate dilution method, the photosensitizer (A) bacteriostatic plate image and (B) colony count statistics for S. aureus and MRSA (20 mW/cm2, 20 min under white light)

References 35

[1]	Gurney, J.; Simonet, C.; Waldetoft, K. W.; Brown, S. P. Nat. Prod. Rep. 2022, 39, 325. doi: 10.1039/D1NP00053E
[2]	Rogers, A. P.; Mileto, S. J.; Lyras, D. Nat. Rev. Microbiol. 2023, 21, 260. doi: 10.1038/s41579-022-00794-x
[3]	Kanj, S. S.; Bassetti, M.; Kiratisin, P.; Rodrigues, C.; Villegas, M. V.; Yu, Y.; van Duin, D. Int. J. Antimicrob. Agents 2022, 60, 106633.
[4]	Dequin, P.-F.; Aubron, C.; Faure, H.; Garot, D.; Guillot, M.; Hamzaoui, O.; Lemiale, V.; Maizel, J.; Mootien, J. Y.; Osman, D.; Simon, M.; Thille, A. W.; Vinsonneau, C.; Kuteifan, K. Ann. Intensive Care 2023, 13, 2. doi: 10.1186/s13613-022-01097-3
[5]	Nardulli, P.; Hall, G. G.; Quarta, A.; Fruscio, G.; Laforgia, M.; Garrisi, V. M.; Ruggiero, R.; Scacco, S.; De Vito, D. Medicina (Lithuania) 2022, 58, 1257. doi: 10.3390/medicina58091257
[6]	Viswanathan, V. K. Gut Microbes 2014, 5, 3. doi: 10.4161/gmic.28027 pmid: 24637595
[7]	Richter, M. F.; Hergenrother, P. J. Ann. N. Y. Acad. Sci. 2019, 1435, 18. doi: 10.1111/nyas.2019.1435.issue-1
[8]	Munoz, K. A.; Hergenrother, P. J. Acc. Chem. Res. 2021, 54, 1322. doi: 10.1021/acs.accounts.0c00895
[9]	Luna, Y.; Yifan, W.; Chenhao, W.; Feng, L.; Weiping, C.; Yonggang, W.; Hongchi, Z. Aust. J. Chem. 2025, ch24146.
[10]	Jana, D.; Zhao, Y. Explor (Beijing) 2022, 2, 20210238.
[11]	Gangopadhyay, M.; Jana, A.; Rajesh, Y.; Bera, M.; Biswas, S.; Chowdhury, N.; Zhao, Y.; Mandal, M.; Singh, N. D. P. Chemistry- Select 2016, 6523.
[12]	Li, Y.; Ma, J.; Liang, W.; Tian, Y.; Li, X.; Wu, D.; Shi, Z.; Fang, X. Chem. Eng. J. 2023, 451, 138531. doi: 10.1016/j.cej.2022.138531
[13]	Yan, Y.-H.; Liang, P.-Z.; Zhou, Y.; Yuan, L.; Peng, X.-J.; Fan, J.-L.; Zhang, X.-B. Acta Chim. Sinica 2023, 81, 1642 (in Chinese). doi: 10.6023/A23050243
	(闫英红, 梁平兆, 邹杨, 袁林, 彭孝军, 樊江莉, 张晓兵, 化学学报, 2023, 81, 1642.) doi: 10.6023/A23050243
[14]	Kamkaew, A.; Lim, S. H.; Lee, H. B.; Kiew, L. V.; Chung, L. Y.; Burgess, K. Chem. Soc. Rev. 2013, 42, 77. doi: 10.1039/C2CS35216H
[15]	Lu, B.; Wang, L.; Tang, H.; Cao, D. J. Mater. Chem. B 2023, 11, 4600. doi: 10.1039/D3TB00545C
[16]	Kang, M.; Zhang, Z.; Song, N.; Li, M.; Sun, P.; Chen, X.; Wang, D.; Tang, B. Z. Aggregate 2020, 80.
[17]	Voskuhl, J.; Giese, M. Aggregate 2021, e124.
[18]	Zhang, Z.; Kang, M.; Tan, H.; Song, N.; Li, M.; Xiao, P.; Yan, D.; Zhang, L.; Wang, D.; Tang, B. Z. Chem. Soc. Rev. 2022, 1983.
[19]	Huang, Y.-Q.; Luo, J.-W.; Li, J.-Q.; Zhang, R.; Liu, X.-F.; Fan, Q.-L.; Huang, W. Acta Chim. Sinica 2024, 82, 903 (in Chinese). doi: 10.6023/A24040115
	(黄艳琴, 罗集文, 李佳启, 张瑞, 刘兴奋, 范曲立, 黄维, 化学学报, 2024, 82, 903.) doi: 10.6023/A24040115
[20]	Li, Y.; Wang, W.; Zhang, Y.-T.; Xiao, S.-Z.; Lan, H.-C.; Geng, P. Acta Chim. Sinica 2024, 82, 443 (in Chinese). doi: 10.6023/A24010035
	(李燕, 王玮, 张毓婷, 肖述章, 兰海闯, 耿鹏, 化学学报, 2024, 82, 443.) doi: 10.6023/A24010035
[21]	Lv, X.; Wu, Y.; Zhang, B.-R.; Guo, W. Acta Chim. Sinica 2023, 81, 359 (in Chinese). doi: 10.6023/A22120487
	(吕鑫, 吴仪, 张勃然, 郭炜, 化学学报, 2023, 81, 359.) doi: 10.6023/A22120487
[22]	Wang, Y.; Liao, J.; Lyu, Y.; Guo, Q.; Zhu, Z.; Wu, X.; Yu, J.; Wang, Q.; Zhu, W.-H. Adv. Funct. Mater. 2023, 33, 2301692. doi: 10.1002/adfm.v33.33
[23]	Wan, Q.; Li, Y.; Ding, K.; Xie, Y.; Fan, J.; Tong, J.; Zeng, Z.; Li, Y.; Zhao, C.; Wang, Z.; Tang, B. Z. J. Am. Chem. Soc. 2023, 145, 1607. doi: 10.1021/jacs.2c09210
[24]	Tianfu, Z.; Zeming, L.; Wenxue, T.; Daoming, Z.; Meng, L.; Yip, L. J. W.; Qinqin, H.; Zhong, T. B. Nano Today 2022, 46, 101620. doi: 10.1016/j.nantod.2022.101620
[25]	Guo, X.-L.; Li, J.-P.; Liu, Z.-Y.; Li, Q. Prog. Chem. 2022, 34, 2489 (in Chinese).
	(郭玲香, 李菊平, 刘志洋, 李全, 化学进展, 2022, 34, 2489.) doi: 10.7536/PC220335
[26]	Yang, X.; Wang, X.; Zhang, X.; Zhang, J.; Lam, J. W. Y.; Sun, H.; Yang, J.; Liang, Y.; Tang, B. Z. Adv. Mater. 2024.
[27]	He, Z.; Gao, Y.; Huang, Z.; Zhan, M.; Tian, S.; Fang, F.; Zhao, D.; Li, Z. a.; Meng, F.; Tang, B. Z.; Luo, L. ACS Nano 2025.
[28]	Peng, Y.-Z.; Guo, G.-C.; Guo, S.; Kong, L.-H.; Lu, T.-B.; Zhang, Z.-M. Angew. Chem. Int. Ed. 2021, 60, 22062.
[29]	Chen, W.; Zhang, Y.; Yi, H.-B.; Wang, F.; Chu, X.; Jiang, J.-H. Angew. Chem. Int. Ed. 2023, 62, e202300162.
[30]	Zhao, M.; Zhang, Y. Y.; Miao, J.; Zhou, H.; Jiang, Y.; Zhang, Y.; Miao, M. Q.; Chen, W.; Xing, W.; Li, Q.; Miao, Q. Q. Adv. Mater. 2024, 36, 2305243. doi: 10.1002/adma.v36.4
[31]	Luo, X.; Li, J.; Li, C.; Heng, L.; Dong, Y. Q.; Liu, Z.; Bo, Z.; Tang, B. Z. Adv. Mater. 2011, 3261.
[32]	Chen, Z.; Li, Z.; Yang, L.; Liang, J.; Yin, J.; Yu, G.-A.; Liu, S. H. Dyes Pigm. 2015, 170.
[33]	Takenaka, K.; Mohanta, S. C.; Sasai, H. Angew. Chem. Int. Ed. 2014, 4675.
[34]	Wan, Q.; Zhang, R.; Zhuang, Z.; Li, Y.; Wang, Z.; Zhang, W.; Hou, J.; Tang, B. Z. Adv. Funct. Mater. 2024, 2312870.
[35]	Li, M.; Xia, J.; Tian, R.; Wang, J.; Fan, J.; Du, J.; Long, S.; Song, X.; Foley, J. W.; Peng, X. J. Am. Chem. Soc. 2018, 14851.

高效率阳离子型光敏剂的设计及其在低辐照剂量光动力抗菌中应用

Design of High Efficiency Cationic Photosensitizer and Its Application in Low Irradiation Dose Photodynamic Antibacterial

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 35

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hua-Nan Wang, He Wu, Ye Zhao, Yi Gu, Gang Chen. Advances in the Process Chemistry of Semisynthetic Antibiotics Based on Complex Natural Products^★ [J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3045-3074.
[2]	Shutian Bu, Yong Wang, Wenjian Yin, Qingyun Wen, Pei Wang, Weiming Zhu. Staurosporine Natural Products Derived from Marine Streptomyces sp. OUCMDZ-5522 [J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2486-2500.
[3]	Jiaqiang Yang, Xurong Zhou, Yangmi Chen, Huixian She. Synthesis and Antibacterial Activities of Osthole Derivatives Containing Phosphonateptide Fragment [J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1306-1314.
[4]	Jianye Yang, Pei Zhou, Qifei Shen, Peijuan Zhang, Yanzi Xu, Bingjie Zhao, Dongfeng Dang. Progress of Organic Radical Materials in Biomedical Applications [J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 4013-4025.
[5]	Yixuan Chen, Zheng Zhao. Aggregation-Induced Emission Photosensitizers for Photodynamic Antimicrobial Therapy [J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 3998-4012.
[6]	Hanyu Jia, Yuewen Yu, Guangxue Feng, BenZhong Tang. Construction of Type I Aggregation-Induced Emission Photosensitizers for Photodynamic Therapy via Photoinduced Electron Transfer Mechanism [J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2530-2537.
[7]	Limin Wang, Xiaoyu Song, Senxiang Cheng, Tong Chen, Deyun Cui. Synthesis and Activity Study of 1,2-Benzisothiazol-3-one Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1897-1906.
[8]	Lingdong Li, Weilun Zhang, Pengfei Liu, Zijie Zhou, Hao Zhou, Zhongtian Du. Synthesis of Gemini-Quaternary Ammonium N-Chloramine Biocides for Antibacterial Applications [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 2041-2048.
[9]	Jiaqiang Yang, Xuejiao Wu, Zicong Lu, Yangmi Chen, Huixian She, Haijun Liu. Design, Synthesis and Antibacterial Activities of Osthole Derivatives Containing Thiazole Fragment [J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3541-3549.
[10]	Haibo Huo, Guixia Li, Shijun Wang, Chun Han, Baojun Shi, Jian Li. Novel γ-Carboline Derivatives as Antibacterial Agents: Synthesis and Antibacterial Evaluation [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 204-215.
[11]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.
[12]	Weizhong Ding, Bingwen Zhang, Yanqing Xue, Yuqi Lin, Zhijun Tang, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. A New Polyketide from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3319-3322.
[13]	Yifang Chen, Xin Luo, Yu Wang, Zhifu Xing, Ju Peng, Jixiang Chen. Design, Synthesis and Antibacterial Activity of 1,3,4-Oxadiazole Sufones Containing Sulfonamide Structure [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 274-284.
[14]	Dan Huang, Xuhua Nong, Jianni Yang, Chen Li, Changri Han, Guangying Chen, Xiaoping Song, Zhenfan Sun, Yang Hui, Wenhao Chen. Study on the Secondary Metabolites of the Endophytic Fungus Aspergillus terreus HQ100X-1 in Scutellaria formosana [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2961-2966.
[15]	Huanhuan Wang, Pu Yang, Hongjin Zhai, Shuo Zhang, Yaquan Cao, Yingxue Yang, Chunli Wu. Design, Synthesis and Activity Evaluation of New Tylosin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 557-572.