Citation: Hao Sun, Shengke Li, Qian Liu, Minzan Zuo, Xueqi Tian, Kaiya Wang, Xiao-Yu Hu. Supramolecular prodrug vesicles for selective antimicrobial therapy employing a chemo-photodynamic strategy[J]. Chinese Chemical Letters, ;2025, 36(3): 109999. doi: 10.1016/j.cclet.2024.109999 shu

Supramolecular prodrug vesicles for selective antimicrobial therapy employing a chemo-photodynamic strategy

Hao Sun ^{a, 1} ,
Shengke Li ^{b, 1,} ,
Qian Liu ^a ,
Minzan Zuo ^a ,
Xueqi Tian ^a ,
Kaiya Wang ^{a, *,} ,
Xiao-Yu Hu ^{a, c, *,}

a.
College of Materials Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing 211106, China
b.
Macao Centre for Research and Development in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macau 999078, China
c.
Qinghai Provincial Key Laboratory of Tibetan Medicine Research and Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, China

walterli@um.edu.mo

kwang6@nuaa.edu.cn

huxy@nuaa.edu.cn

Received Date: 1 March 2024
Revised Date: 29 April 2024
Accepted Date: 10 May 2024
Available Online: 11 May 2024

Figures(6)

Supramolecular prodrug vesicles (H-4⊃B-2@MB) with selective antibacterial activity have been successfully constructed. Specifically, a natural antibiotic prodrug (B-2) with glutathione (GSH)-responsiveness was synthesized. The hydrophobic interaction between B-2 and a novel water-soluble cavitand with deep cavity (H-4) resulted in the formation of a host-guest complex, which further self-assembled into supramolecular vesicles. The formed vesicles could effectively encapsulate the photosensitizer methylene blue (MB), enabling co-delivery of antibiotics and photosensitizers in the presence of GSH. Moreover, upon excitation at 630 nm, the photosensitizers generate reactive oxygen species (ROS), effectively eradicating E. coli through combined chemo-photodynamic therapy. Considering that GSH is predominantly present in Gram-negative bacteria such as E. coli, this strategy exhibits substantial potential for selectively inhibiting bacteria characterized by high GSH levels to regulate bacterial colony equilibrium.
- Supramolecular prodrug,
- Selective antibacterial activity,
- Host-guest complex,
- Cavitand,
- Combination therapy
1. [1]
  F. Li, M. Zang, S. Liu, et al., J. Mater. Chem. B 9 (2021) 2066–2072. doi: 10.1039/d0tb02786c
2. [2]
  D. He, Y. Tan, P. Li, et al., Chin. Chem. Lett. 32 (2021) 1743–1746. doi: 10.1016/j.cclet.2020.12.034
3. [3]
  V.-N. Nguyen, Z. Zhao, B.Z. Tang, et al., Chem. Soc. Rev. 51 (2022) 3324–3340. doi: 10.1039/d1cs00647a
4. [4]
  Y. Zhao, L. Chen, Y. Wang, et al., Nano Res. 14 (2021) 4417–4441. doi: 10.1007/s12274-021-3417-4
5. [5]
  X. Tian, S. Li, K. Velmurugan, et al., Mater. Chem. Front. 7 (2023) 2484–2492. doi: 10.1039/d3qm00153a
6. [6]
  M.M.S. Lee, E.Y. Yu, D. Yan, et al., ACS Nano 17 (2023) 17004–17020. doi: 10.1021/acsnano.3c04266
7. [7]
  X. Zhang, X. Chen, Y. Guo, et al., Angew. Chem. Int. Ed. 60 (2021) 14013–14021. doi: 10.1002/anie.202102059
8. [8]
  X. Hu, H. Zhang, Y. Wang, et al., Chem. Eng. J. 450 (2022) 138129. doi: 10.1016/j.cej.2022.138129
9. [9]
  R. Bholakant, B. Dong, X. Zhou, et al., J. Mater. Chem. B 9 (2021) 8718–8738. doi: 10.1039/d1tb01771c
10. [10]
  D. Lee, J. Shin, H. Son, et al., Nanoscale Adv. 5 (2023) 1600–1610. doi: 10.1039/d3na00043e
11. [11]
  J. Xu, Y. Lai, F. Wang, et al., Chin. Chem. Lett. 34 (2023) 108332. doi: 10.1016/j.cclet.2023.108332
12. [12]
  R. Wu, H. Wang, L. Hai, et al., Chin. Chem. Lett. 31 (2020) 189–192. doi: 10.1016/j.cclet.2019.05.004
13. [13]
  K. Liu, Y. Liu, Y. Yao, et al., Angew. Chem. Int. Ed. 52 (2013) 8285–8289. doi: 10.1002/anie.201303387
14. [14]
  M. Piksa, C. Lian, I.C. Samuel, et al., Chem. Soc. Rev. 52 (2023) 1697–1722. doi: 10.1039/d0cs01051k
15. [15]
  J. Xie, Y. Wang, W. Choi, et al., Chem. Soc. Rev. 50 (2021) 9152–9201. doi: 10.1039/d0cs01370f
16. [16]
  M. Overchuk, R.A. Weersink, B.C. Wilson, et al., ACS Nano 17 (2023) 7979–8003. doi: 10.1021/acsnano.3c00891
17. [17]
  B. Li, W. Wang, L. Zhao, et al., ACS Nano 17 (2023) 4601–4618. doi: 10.1021/acsnano.2c10694
18. [18]
  Y. Yang, P. He, Y. Wang, et al., Angew. Chem. Int. Ed. 56 (2017) 16239–16242. doi: 10.1002/anie.201708971
19. [19]
  D. Lee, L. Dong, Y. Kim, et al., Adv. Healthc. Mater. 12 (2023) 2203136. doi: 10.1002/adhm.202203136
20. [20]
  X. Huang, C. Lu, W. Zhang, et al., ACS Nano 17 (2023) 14893–14903. doi: 10.1021/acsnano.3c03458
21. [21]
  K. Wang, Q. Liu, L. Zhou, et al., Chin. Chem. Lett. 34 (2023) 108559. doi: 10.1016/j.cclet.2023.108559
22. [22]
  K. Wang, R. Zhang, Z. Song, et al., Adv. Sci. 10 (2023) 2206897. doi: 10.1002/advs.202206897
23. [23]
  T. Zhang, K. Wang, X. Huang, et al., Chem. Eur. J. 29 (2023) e202203738. doi: 10.1002/chem.202203738
24. [24]
  Y. Zhou, H. Tang, H. Wu, et al., Chin. Chem. Lett. 35 (2024) 108626. doi: 10.1016/j.cclet.2023.108626
25. [25]
  S. Li, J.J. Li, Y.Y. Zhao, et al., ACS Nano 17 (2023) 25468–25482. doi: 10.1021/acsnano.3c09140
26. [26]
  S. Li, Y. Wang, X. Wang, et al., ACS Nano 17 (2023) 22399–22409. doi: 10.1021/acsnano.3c04718
27. [27]
  Q. Cheng, S. Li, Y. Ma, et al., Chin. Chem. Lett. 31 (2020) 1235–1238. doi: 10.1016/j.cclet.2019.10.020
28. [28]
  G. Sun, M. Zuo, Z. Xu, et al., ACS Appl. Bio. Mater. 5 (2022) 3320–3328. doi: 10.1021/acsabm.2c00318
29. [29]
  R.J. Hooley, S.R. Shenoy, J. Rebek, Jr., Org. Lett. 10 (2008) 5397–5400. doi: 10.1021/ol8022775
30. [30]
  Y. Liang, M. Zhu, T. Xu, et al., Molecules 28 (2023) 5715. doi: 10.3390/molecules28155715
31. [31]
  J. Xing, Q. Gong, R. Zou, et al., Chin. Chem. Lett. 34 (2023) 107786. doi: 10.1016/j.cclet.2022.107786
32. [32]
  G.V. Smirnova, O.N. Oktyabrsky, Biochemistry 70 (2005) 1199–1211. doi: 10.1007/s10541-005-0248-3
33. [33]
  M.B. Hillyer, C.L.D. Gibb, P. Sokkalingam, et al., Org. Lett. 18 (2016) 4048–4051. doi: 10.1021/acs.orglett.6b01903
34. [34]
  F.U. Rahman, H.N. Feng, Y. Yu, Org. Chem. Front. 6 (2019) 998–1001. doi: 10.1039/c9qo00049f
35. [35]
  X. Tian, M. Zuo, P. Niu, et al., ACS Appl. Mater. Interfaces 13 (2021) 37466–37474. doi: 10.1021/acsami.1c07106
36. [36]
  P. Koprowski, A. Kubalski, Pflugers Arch. 438 (1999) 361–364. doi: 10.1007/s004240050921
1. [1]
  Ningyue Xu , Jun Wang , Lei Liu , Changyang Gong . Injectable hydrogel-based drug delivery systems for enhancing the efficacy of radiation therapy: A review of recent advances. Chinese Chemical Letters, 2024, 35(8): 109225-. doi: 10.1016/j.cclet.2023.109225
2. [2]
  Tingting Hu , Chao Shen , Xueyan Wang , Fengbo Wu , Zhiyao He . Tumor microenvironment-sensitive polymeric nanoparticles for synergetic chemo-photo therapy. Chinese Chemical Letters, 2024, 35(11): 109562-. doi: 10.1016/j.cclet.2024.109562
3. [3]
  Cheng He , Renlan Huang , Lingling Wei , Qiuhui He , Jinbo Liu , Jiao Chen , Ge Gao , Cheng Yang , Wanhua Wu . Uncovering the mask of sensitizers to switch on the TTA-UC emission by supramolecular host-guest complexation. Chinese Chemical Letters, 2025, 36(4): 110103-. doi: 10.1016/j.cclet.2024.110103
4. [4]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
5. [5]
  Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818
6. [6]
  Jianmei Guo , Yupeng Zhao , Lei Ma , Yongtao Wang . Ultra-long room temperature phosphorescence, intrinsic mechanisms and application based on host-guest doping systems. Chinese Journal of Structural Chemistry, 2024, 43(9): 100335-100335. doi: 10.1016/j.cjsc.2024.100335
7. [7]
  Huijie An , Chen Yang , Zhihui Jiang , Junjie Yuan , Zhongming Qiu , Longhao Chen , Xin Chen , Mutu Huang , Linlang Huang , Hongju Lin , Biao Cheng , Hongjiang Liu , Zhiqiang Yu . Luminescence-activated Pt(Ⅳ) prodrug for in situ triggerable cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109134-. doi: 10.1016/j.cclet.2023.109134
8. [8]
  Shuheng Zhang , Yuanyuan Zhang , Wanyu Wang , Yuzhu Hu , Xinchuan Chen , Bilan Wang , Xiang Gao . A combination strategy of DOX and VEGFR-2 targeted inhibitor based on nanomicelle for enhancing lymphoma therapy. Chinese Chemical Letters, 2024, 35(12): 109658-. doi: 10.1016/j.cclet.2024.109658
9. [9]
  Xianchen Hu , Junli Yang , Fang Gao , Zhiyong Zhao , Simin Liu . Highly selective [4+4] cross-photodimerization of (4a-azonia)anthracenes driven by confinement of D-A hetero-guest pair in cucurbit[10]uril host. Chinese Chemical Letters, 2025, 36(3): 109967-. doi: 10.1016/j.cclet.2024.109967
10. [10]
  Lin Li , Bingjun Sun , Jin Sun , Lin Chen , Zhonggui He . Binary prodrug nanoassemblies combining chemotherapy and ferroptosis activation for efficient triple-negative breast cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109538-. doi: 10.1016/j.cclet.2024.109538
11. [11]
  Chao Zhang , Ai-Feng Liu , Shihui Li , Fang-Yuan Chen , Jun-Tao Zhang , Fang-Xing Zeng , Hui-Chuan Feng , Ping Wang , Wen-Chao Geng , Chuan-Rui Ma , Dong-Sheng Guo . A supramolecular formulation of icariin@sulfonatoazocalixarene for hypoxia-targeted osteoarthritis therapy. Chinese Chemical Letters, 2025, 36(1): 109752-. doi: 10.1016/j.cclet.2024.109752
12. [12]
  Wenjia Wang , Xingyue He , Xiaojie Wang , Tiantian Zhao , Osamu Muraoka , Genzoh Tanabe , Weijia Xie , Tianjiao Zhou , Lei Xing , Qingri Jin , Hulin Jiang . Glutathione-depleted cyclodextrin pseudo-polyrotaxane nanoparticles for anti-inflammatory oxaliplatin (Ⅳ) prodrug delivery and enhanced colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108656-. doi: 10.1016/j.cclet.2023.108656
13. [13]
  Wei Su , Xiaoyan Luo , Peiyuan Li , Ying Zhang , Chenxiang Lin , Kang Wang , Jianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522
14. [14]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
15. [15]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
16. [16]
  Mengjuan Sun , Muye Zhou , Yifang Xiao , Hailei Tang , Jinhua Chen , Ruitao Zhang , Chunjiayu Li , Qi Ya , Qian Chen , Jiasheng Tu , Qiyue Wang , Chunmeng Sun . Reversibly size-switchable polyion complex micelles for antiangiogenic cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109110-. doi: 10.1016/j.cclet.2023.109110
17. [17]
  Xueru Zhao , Aopu Wang , Shimin Wang , Zhijie Song , Li Ma , Li Shao . Adsorption and visual detection of nitro explosives by pillar[n]arenes-based host–guest interactions. Chinese Chemical Letters, 2025, 36(4): 110205-. doi: 10.1016/j.cclet.2024.110205
18. [18]
  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
19. [19]
  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
20. [20]
  Panpan Wang , Hongbao Fang , Mengmeng Wang , Guandong Zhang , Na Xu , Yan Su , Hongke Liu , Zhi Su . A mitochondria targeting Ir(III) complex triggers ferroptosis and autophagy for cancer therapy: A case of aggregation enhanced PDT strategy for metal complexes. Chinese Chemical Letters, 2025, 36(1): 110099-. doi: 10.1016/j.cclet.2024.110099

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(79)
HTML views(7)

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