Aggregation-Enhanced Sonodynamic Activity of Phthalocyanine–Artesunate Conjugates
Peng-Hui Zhao
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorYu-Lin Wu
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorXue-Yan Li
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorLin-Lin Feng
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorLing Zhang
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorBi-Yuan Zheng
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorCorresponding Author
Dr. Mei-Rong Ke
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorCorresponding Author
Prof. Jian-Dong Huang
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorPeng-Hui Zhao
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorYu-Lin Wu
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorXue-Yan Li
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorLin-Lin Feng
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorLing Zhang
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorBi-Yuan Zheng
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorCorresponding Author
Dr. Mei-Rong Ke
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorCorresponding Author
Prof. Jian-Dong Huang
College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou, Fujian, 350108 China
Search for more papers by this authorAbstract
The clinical prospect of sonodynamic therapy (SDT) has not been fully realized due to the scarcity of efficient sonosensitizers. Herein, we designed phthalocyanine–artesunate conjugates (e.g. ZnPcT4A), which could generate up to ca. 10-fold more reactive oxygen species (ROS) than the known sonosensitizer protoporphyrin IX. Meanwhile, an interesting and significant finding of aggregation-enhanced sonodynamic activity (AESA) was observed for the first time. ZnPcT4A showed about 60-fold higher sonodynamic ROS generation in the aggregated form than in the disaggregated form in aqueous solutions. That could be attributed to the boosted ultrasonic cavitation of nanostructures. The level of the AESA effect depended on the aggregation ability of sonosensitizer molecules and the particle size of their aggregates. Moreover, biological studies demonstrated that ZnPcT4A had high anticancer activities and biosafety. This study thus opens up a new avenue the development of efficient organic sonosensitizers.
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References
- 1
- 1aS. Umemura, N. Yumita, R. Nishigaki, K. Umemura, Ultrason. Symp. Proc. 1989, 2, 955–960;
10.1109/ULTSYM.1989.67130 Google Scholar
- 1bS. Son, J. H. Kim, X. Wang, C. Zhang, S. A. Yoon, J. Shin, A. Sharma, M. H. Lee, L. Cheng, J. Wu, J. S. Kim, Chem. Soc. Rev. 2020, 49, 3244–3261.
- 2
- 2aX. Xing, S. Zhao, T. Xu, L. Huang, Y. Zhang, M. Lan, C. Lin, X. Zheng, P. Wang, Coord. Chem. Rev. 2021, 445, 214087;
- 2bK. Zhang, H. Xu, X. Jia, Y. Chen, M. Ma, L. Sun, H. Chen, ACS Nano 2016, 10, 10816–10828;
- 2cY. Wang, Y. Xu, S. Dong, P. Wang, W. Chen, Z. Lu, D. Ye, B. Pan, D. Wu, C. D. Vecitis, G. Gao, Nat. Commun. 2021, 12, 3508.
- 3
- 3aX. Lin, S. Liu, X. Zhang, R. Zhu, S. Chen, X. Chen, J. Song, H. Yang, Angew. Chem. Int. Ed. 2020, 59, 1682–1688; Angew. Chem. 2020, 132, 1699–1705;
- 3bF. Gong, L. Cheng, N. Yang, O. Betzer, L. Feng, Q. Zhou, Y. Li, R. Chen, R. Popovtzer, Z. Liu, Adv. Mater. 2019, 31, 1900730;
- 3cJ. Li, Y. Luo, K. Pu, Angew. Chem. Int. Ed. 2021, 60, 12682–12705; Angew. Chem. 2021, 133, 12792–12815.
- 4
- 4aW. Um, H. Ko, D. G. You, S. Lim, G. Kwak, M. K. Shim, S. Yang, J. Lee, Y. Song, K. Kim, J. H. Park, Adv. Mater. 2020, 32, 1907953;
- 4bT. Tuziuti, K. Yasui, M. Sivakumar, Y. Iida, N. Miyoshi, J. Phys. Chem. A 2005, 109, 4869–4872;
- 4cV. Choi, M. A. Rajora, G. Zheng, Bioconjugate Chem. 2020, 31, 967–989.
- 5
- 5aZ. Li, J. Han, L. Yu, X. Qian, H. Xing, H. Lin, M. Wu, T. Yang, Y. Chen, Adv. Funct. Mater. 2018, 28, 1800145;
- 5bQ. Wu, F. Zhang, X. Pan, Z. Huang, Z. Zeng, H. Wang, J. Jiao, X. Xiong, L. Bai, D. Zhou, H. Liu, Adv. Mater. 2021, 33, 2007073;
- 5cS. Bai, N. Yang, X. Wang, F. Gong, L. Cheng, ACS Nano 2020, 14, 15119–15130;
- 5dX. Tan, J. Huang, Y. Wang, S. He, L. Jia, Y. Zhu, K. Pu, Y. Zhang, X. Yang, Angew. Chem. Int. Ed. 2021, 60, 14051–14059; Angew. Chem. 2021, 133, 14170–14178.
- 6X. Lin, J. Song, X. Chen, H. Yang, Angew. Chem. Int. Ed. 2020, 59, 14212–14233; Angew. Chem. 2020, 132, 14316–14338.
- 7
- 7aJ. Zhu, C. Chu, D. Li, X. Pang, H. Zheng, J. Wang, Y. Shi, Y. Zhang, Y. Cheng, E. Ren, J. Cheng, X. Chen, G. Liu, Adv. Funct. Mater. 2019, 29, 1904056;
- 7bH. Zhang, L. Xing, Y. Liu, W. Yin, H. Li, C. Zhao, H. Li, Q. Meng, L. Wei, A. B. Nukhet, PLoS One 2014, 9, e86003;
- 7cH. J. Chen, X. R. Huang, X. B. Zhou, B. Y. Zheng, J. D. Huang, Chem. Commun. 2015, 51, 4681–4684;
- 7dA. Jh, B. Zx, C. Ya, C. Sh, W. D. Wei, W. A. Yong, G. E. Yu, B. Xsa, Biomaterials 2021, 269, 120636;
- 7eS. Liang, X. Deng, P. Ma, Z. Cheng, J. Lin, Adv. Mater. 2020, 32, 2003214.
- 8
- 8aM. Yuan, S. Liang, Y. Zhou, X. Xiao, B. Liu, C. Yang, P. Ma, Z. Cheng, J. Lin, Nano Lett. 2021, 21, 6042–6050;
- 8bP. Yan, L. H. Liu, P. Wang, ACS Appl. Bio Mater. 2020, 3, 3456–3475;
- 8cF. Gong, L. Cheng, N. Yang, Y. Gong, Y. Ni, S. Bai, X. Wang, M. Chen, Q. Chen, Z. Liu, Nat. Commun. 2020, 11, 3712;
- 8dW. Xu, D. Wang, B. Z. Tang, Angew. Chem. Int. Ed. 2021, 60, 7476–7487; Angew. Chem. 2021, 133, 7552–7563.
- 9
- 9aX. Li, D. Lee, J. D. Huang, J. Yoon, Angew. Chem. Int. Ed. 2018, 57, 9885–9890; Angew. Chem. 2018, 130, 10033–10038;
- 9bM. Yang, T. Yang, C. Mao, Angew. Chem. Int. Ed. 2019, 58, 14066–14080; Angew. Chem. 2019, 131, 14204–14219.
- 10H. N. Xu, H. J. Chen, B. Y. Zheng, Y. Q. Zheng, M. R. Ke, J. D. Huang, Ultrason. Sonochem. 2015, 22, 125–131.
- 11
- 11aX. Li, C. Y. Kim, S. Lee, D. Lee, H. Chung, G. Kim, S. Heo, C. Kim, K. Hong, J. Yoon, J. Am. Chem. Soc. 2017, 139, 10880–10886;
- 11bJ. Y. Liu, P. C. Lo, X. J. Jiang, W. P. Fong, Ng, Dennis, Dalton Trans. 2009, 21, 4041–4260.
- 12
- 12aS. J. Chung, K. Y. Kwon, S. W. Lee, J. I. Jin, C. H. Lee, C. E. Lee, Y. Park, Adv. Mater. 1998, 10, 1112–1116;
10.1002/(SICI)1521-4095(199810)10:14<1112::AID-ADMA1112>3.0.CO;2-P CAS Web of Science® Google Scholar
- 12bS. W. Thomas, G. D. Joly, T. M. Swager, Chem. Rev. 2007, 107, 1339–1386.
- 13M. Li, J. Xia, R. Tian, J. Wang, J. Fan, J. Du, S. Long, X. Song, J. W. Foley, X. Peng, J. Am. Chem. Soc. 2018, 140, 14851–14859.
- 14M. Zhu, J. Lu, Y. Hu, Y. Liu, S. Hu, C. Zhu, Environ. Sci. Pollut. Res. Int. 2020, 27, 31289–31299.
- 15X. Pan, L. Bai, H. Wang, Q. Wu, H. Wang, S. Liu, B. Xu, X. Shi, H. Liu, Adv. Mater. 2018, 30, 1800180.
- 16B. Y. Zheng, L. Wang, Q. Y. Hu, J. Shi, M. R. Ke, J. D. Huang, Dyes Pigm. 2020, 177, 108286.
- 17
- 17aU. Goswami, R. Kandimalla, S. Kalita, A. Chattopadhyay, S. S. Ghosh, ACS Omega 2018, 3, 11504–11516;
- 17bR. C. H. Wong, D. K. P. Ng, W. P. Fong, P. C. Lo, Chem. Eur. J. 2017, 23, 16505–16515.
- 18Y. Jia, Y. Cui, J. Fei, M. Du, L. Dai, J. Li, Y. Yang, Adv. Funct. Mater. 2012, 22, 1446–1453.
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