Citation: Qianyun Ye, Yuanyuan Liang, Yuhe Yuan, Xiaohuan Sun, Liqi Zhu, Xuan Wu, Jie Han, Rong Guo. pH-responsive chiral supramolecular cysteine-Zn²⁺-indocyanine green assemblies for triple-level chirality-specific anti-tumor efficacy[J]. Chinese Chemical Letters, ;2025, 36(5): 110432. doi: 10.1016/j.cclet.2024.110432 shu

pH-responsive chiral supramolecular cysteine-Zn²⁺-indocyanine green assemblies for triple-level chirality-specific anti-tumor efficacy

Qianyun Ye ^a ,
Yuanyuan Liang ^b ,
Yuhe Yuan ^a ,
Xiaohuan Sun ^{a, *,} ,
Liqi Zhu ^b ,
Xuan Wu ^a ,
Jie Han ^{a, *,} ,
Rong Guo ^a

a.
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China
b.
College of Veterinary Medicine, Yangzhou University, Yangzhou 225002, China

xhuansun@yzu.edu.cn

hanjie@yzu.edu.cn

Received Date: 23 April 2024
Revised Date: 6 September 2024
Accepted Date: 8 September 2024
Available Online: 12 September 2024

Figures(7)

Chirality, ubiquitous in living matter, plays vital roles in a series of physiological processes. The clarification of the multiple functions of chirality in bioapplications may provide innovative methodologies for engineering anti-tumor agents. Nevertheless, the related research has been rarely explored. In this study, the chiral supramolecular l/d-cysteine (Cys)-Zn²⁺-indocyanine green (ICG) nanoparticles were constructed through the coordination interaction between l/d-Cys and Zn²⁺, followed by the encapsulation of ICG. Experimental findings revealed that the d-Cys-Zn²⁺-ICG exhibited 17.31 times higher binding affinity toward phospholipid-composed liposomes compared to l-Cys-Zn²⁺-ICG. Furthermore, driven by chirality-specific interaction, a 2.07 folds greater cellular internalization of d-Cys-Zn²⁺-ICG than l-Cys-Zn²⁺-ICG was demonstrated. Additionally, the triple-level chirality-dependent photothermal, photodynamic and Zn²⁺ releasing anti-tumor effects of l/d Cys-Zn²⁺-ICG in vitro were verified. As a result, the d-formed nanoparticles achieved 1.93 times higher anti-tumor efficiency than the l-formed ones. The triple-level chirality-mediated anti-tumor effect highlighted in this study underscores the enormous potential of chirality in biomedicine and holds substantial significance in improving cancer therapeutic efficacy.
- Chirality,
- pH-responsiveness,
- Photothermal therapy,
- Photodynamic therapy,
- Zn²⁺ release
1. [1]
  S. Huang, H. Yu, Q. Li, Adv Sci. 8 (2021) 2002132.
2. [2]
  K. Hou, J. Zhao, H. Wang, et al., Nat. Commun. 11 (2020) 4790.
3. [3]
  D.A. Nicholson, A. Sengupta, D.J. Nesbitt, J. Phys. Chem. B 124 (2020) 11561–11572. doi: 10.1021/acs.jpcb.0c07420
4. [4]
  Y. Ma, L. Shi, H. Yue, X. Gao, Colloids Surf. B: Biointerfaces 195 (2020) 111268.
5. [5]
  P. Chen, P.P. Lv, C.S. Guo, et al., Chin. Chem. Lett. 34 (2023) 108041.
6. [6]
  Y. Ding, C. Wang, B. Lu, Y. Yao, Front. Chem. 9 (2021) 775436.
7. [7]
  Y. Wang, H. Zhong, J. Yang, Y. Yao, L. Li, Chin. Chem. Lett. 34 (2023) 108452.
8. [8]
  Y. Zhang, Y. Wang, T. Chen, et al., Chem. Commun. 59 (2023) 8266–8269. doi: 10.1039/d3cc01929b
9. [9]
  C.Q. Zhou, Y.Y. Ren, J. Han, et al., J. Am. Chem. Soc. 140 (2018) 9417–9425. doi: 10.1021/jacs.7b12178
10. [10]
  T. Tian, D. Wei, L.L. Ge, et al., J. Colloid Interface Sci. 601 (2021) 746–757.
11. [11]
  B.B. Xu, J. Ye, Y. Yuan, W.L. Duan, ACS Catal. 8 (2018) 11735–11740. doi: 10.1021/acscatal.8b03912
12. [12]
  W.Y. Ma, B.L. Wang, Y.G. Yang, J.Y. Li, Chin. Chem. Lett. 32 (2021) 3916–3920.
13. [13]
  X. Sun, Q. Ye, Y. Liang, et al., J. Colloid Interface Sci. 657 (2024) 993–1002.
14. [14]
  J. Zhou, J. Gu, X. Sun, et al., Adv. Sci. 11 (2024) 2308493.
15. [15]
  P.L. Gao, S. Chen, S. Liu, et al., ACS Appl. Mater. Interfaces 13 (2021) 56456–56464. doi: 10.1021/acsami.1c16091
16. [16]
  C.L. Hao, A.H. Qu, L.G. Xu, et al., J. Am. Chem. Soc. 141 (2019) 1091–1099. doi: 10.1021/jacs.8b11856
17. [17]
  G.Y. Yuan, Z. Xi, C. Wang, et al., Acta Phys. Chim. Sin. 39 (2023) 2212061. doi: 10.3866/pku.whxb202212061
18. [18]
  H. Zhang, C. Hao, A. Qu, et al., Angew. Chem. Int. Ed. 59 (2020) 7131–7138. doi: 10.1002/anie.202002028
19. [19]
  F. Li, Y. Li, X. Yang, et al., Angew. Chem. Int. Ed. 57 (2018) 2377–2382. doi: 10.1002/anie.201712453
20. [20]
  B. Chen, L. Song, Y. Yuan, et al., ACS Appl. Mater. Interfaces 15 (2023) 651–661. doi: 10.1021/acsami.2c19291
21. [21]
  L. Xu, X. Wang, W. Wang, et al., Nature 601 (2022) 366–373. doi: 10.1038/s41586-021-04243-2
22. [22]
  X. Dou, N. Mehwish, C. Zhao, et al., Acc. Chem. Res. 53 (2020) 852–862. doi: 10.1021/acs.accounts.0c00012
23. [23]
  D. Lovison, D. Alessi, L. Allegri, et al., Chem. Eur. J. 28 (2022) e202200200.
24. [24]
  C.L. Wang, X. Wang, D.D. Wang, et al., Chin. Chem. Lett. 34 (2023) 107332.
25. [25]
  J. Yeom, P.P.G. Guimaraes, H.M. Ahn, et al., Adv. Mater. 32 (2020) 1903878.
26. [26]
  N.N. Zhang, H.-R. Sun, S. Liu, et al., CCS Chem. 4 (2022) 660–670. doi: 10.31635/ccschem.021.202000637
27. [27]
  Y. Zhang, F. Wang, C. Liu, et al., ACS Nano 12 (2018) 651–661. doi: 10.1021/acsnano.7b07746
28. [28]
  Y. Teng, M. Li, X. Huang, J. Ren, ACS Appl. Bio. Mater. 3 (2020) 5020–5029. doi: 10.1021/acsabm.0c00522
29. [29]
  Q. Meng, R. Zhao, P. Cao, et al., Chem. Eng. J. 447 (2022) 137471.
30. [30]
  N.J. Pace, E. Weerapana, Biomolecules 4 (2014) 419–434. doi: 10.3390/biom4020419
31. [31]
  Q.M. Ke, P. Jing, Y.H. Wan, et al., J. Colloid Interface Sci. 654 (2024) 224–234.
32. [32]
  W.Q. Ding, H.J. Yu, S.E. Lind, Cancer Lett. 271 (2008) 251–259.
33. [33]
  Q. Cui, Y. Zhao, K. Qi, Y. Yan, J. Taiwan Inst. Chem. Eng. 142 (2023) 104679.
34. [34]
  W. Li, H. Zhang, X. Guo, et al., ACS Appl. Mater. Interfaces 9 (2017) 3354–3367. doi: 10.1021/acsami.6b13351
35. [35]
  C.E. Smith, A. Shkumatov, S.G. Withers, et al., ACS Nano 7 (2013) 9599–9610. doi: 10.1021/nn4026228
36. [36]
  Q. Zhang, T. Zhuang, X. Sun, et al., J. Colloid Interface Sci. 665 (2024) 1–9.
37. [37]
  Z.L. Xu, J. Chen, Y.A. Li, et al., J. Colloid Interface Sci. 628 (2022) 1033–1043. doi: 10.12688/f1000research.122775.1
38. [38]
  S. Wang, J.W. Zhang, W. Li, et al., Carbohydr. Polym. 296 (2022) 119940.
39. [39]
  L.S. Lin, J.F. Wang, J. Song, et al., Theranostics 9 (2019) 7200–7209. doi: 10.7150/thno.39831
40. [40]
  X.X. Fan, C.F. Ren, K.K. Ning, et al., ACS Appl. Mater. Interfaces 15 (2023) 58251–58259. doi: 10.1021/acsami.3c15463
41. [41]
  Y.P. Jiang, K. Shao, F.L. Zhang, et al., Aggregate 4 (2023) e321.
42. [42]
  F.L. Zhao, A. Gao, Q. Liao, et al., Adv. Funct. Mater. (2024) 2311812.
43. [43]
  M. Yang, N.B. Nazhat, X. Jiang, et al., Br. J. Haematol. 95 (2003) 339–344.
44. [44]
  M.M. He, R. Wang, R.F. Zhang, et al., Adv. Funct. Mater. 33 (2023) 2300780.
45. [45]
  J.X. Lu, W.J. Wang, Z. Xu, et al., J. Colloid Interface Sci. 633 (2023) 657–667.
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Yupeng Liu , Hui Wang , Songnan Qu . Review on near-infrared absorbing/emissive carbon dots: From preparation to multi-functional application. Chinese Chemical Letters, 2025, 36(5): 110618-. doi: 10.1016/j.cclet.2024.110618
5. [5]
  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
6. [6]
  Di An , Mingdong She , Ziyang Zhang , Ting Zhang , Miaomiao Xu , Jinjun Shao , Qian Shen , Xuna Tang . Light-responsive nanomaterials for biofilm removal in root canal treatment. Chinese Chemical Letters, 2025, 36(2): 109841-. doi: 10.1016/j.cclet.2024.109841
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  Wenkai Liu , Yanxian Hou , Weijian Liu , Ran Wang , Shan He , Xiang Xia , Chengyuan Lv , Hua Gu , Qichao Yao , Qingze Pan , Zehou Su , Danhong Zhou , Wen Sun , Jiangli Fan , Xiaojun Peng . Se-substituted pentamethine cyanine for anticancer photodynamic therapy mediated using the hot band absorption process. Chinese Chemical Letters, 2024, 35(12): 109631-. doi: 10.1016/j.cclet.2024.109631
11. [11]
  Du Liu , Yuyan Li , Hankun Zhang , Benhua Wang , Chaoyi Yao , Minhuan Lan , Zhanhong Yang , Xiangzhi Song . Three-in-one erlotinib-modified NIR photosensitizer for fluorescence imaging and synergistic chemo-photodynamic therapy. Chinese Chemical Letters, 2025, 36(2): 109910-. doi: 10.1016/j.cclet.2024.109910
12. [12]
  Liangliang Jia , Ye Hong , Xinyu He , Ying Zhou , Liujiao Ren , Hongjun Du , Bin Zhao , Bin Qin , Zhe Yang , Di Gao . Fighting hypoxia to improve photodynamic therapy-driven immunotherapy: Alleviating, exploiting and disregarding. Chinese Chemical Letters, 2025, 36(2): 109957-. doi: 10.1016/j.cclet.2024.109957
13. [13]
  Baoli Yin , Xinlin Liu , Zhe Li , Zhifei Ye , Youjuan Wang , Xia Yin , Sulai Liu , Guosheng Song , Shuangyan Huan , Xiao-Bing Zhang . Ratiometric NIR-Ⅱ fluorescent organic nanoprobe for imaging and monitoring tumor-activated photodynamic therapy. Chinese Chemical Letters, 2025, 36(5): 110119-. doi: 10.1016/j.cclet.2024.110119
14. [14]
  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
15. [15]
  Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
16. [16]
  Xiao-Fang Lv , Xiao-Yun Ran , Yu Zhao , Rui-Rui Zhang , Li-Na Zhang , Jing Shi , Ji-Xuan Xu , Qing-Quan Kong , Xiao-Qi Yu , Kun Li . Combing NIR-Ⅱ molecular dye with magnetic nanoparticles for enhanced photothermal theranostics with a 95.6% photothermal conversion efficiency. Chinese Chemical Letters, 2025, 36(4): 110027-. doi: 10.1016/j.cclet.2024.110027
17. [17]
  Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H₂O₂ for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
18. [18]
  Yunli Xu , Xuwen Da , Lei Wang , Yatong Peng , Wanpeng Zhou , Xiulian Liu , Yao Wu , Wentao Wang , Xuesong Wang , Qianxiong Zhou . Ru(Ⅱ)-based aggregation-induced emission (AIE) agents with efficient ¹O₂ generation, photo-catalytic NADH oxidation and anticancer activity. Chinese Chemical Letters, 2025, 36(5): 110168-. doi: 10.1016/j.cclet.2024.110168
19. [19]
  Xiangqian Cao , Chenkai Yang , Xiaodong Zhu , Mengxin Zhao , Yilin Yan , Zhengnan Huang , Jinming Cai , Jingming Zhuang , Shengzhou Li , Wei Li , Bing Shen . Synergistic enhancement of chemotherapy for bladder cancer by photothermal dual-sensitive nanosystem with gold nanoparticles and PNIPAM. Chinese Chemical Letters, 2024, 35(8): 109199-. doi: 10.1016/j.cclet.2023.109199
20. [20]
  Yongkang Yue , Zhou Xu , Kaiqing Ma , Fangjun Huo , Xuemei Qin , Kuanshou Zhang , Caixia Yin . HSA shrinkage optimizes the photostability of embedded dyes fundamentally to amplify their efficiency as photothermal materials. Chinese Chemical Letters, 2024, 35(8): 109223-. doi: 10.1016/j.cclet.2023.109223

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(24)
HTML views(5)

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

pH-responsive chiral supramolecular cysteine-Zn2+-indocyanine green assemblies for triple-level chirality-specific anti-tumor efficacy

Metrics

通讯作者: 陈斌, bchen63@163.com

pH-responsive chiral supramolecular cysteine-Zn²⁺-indocyanine green assemblies for triple-level chirality-specific anti-tumor efficacy