Citation: Jie Yang, Dihua Dai, Lianjun Ma, Ying-Wei Yang. Molecular-scale drug delivery systems loaded with oxaliplatin for supramolecular chemotherapy[J]. Chinese Chemical Letters, ;2021, 32(2): 729-734. doi: 10.1016/j.cclet.2020.08.035 shu

Molecular-scale drug delivery systems loaded with oxaliplatin for supramolecular chemotherapy

International Joint Research Laboratory of Nano-Micro Architecture Chemistry, College of Chemistry, and Department of Endoscopics, China-Japan Union Hospital of Jilin University, Jilin University, Changchun 130012, China

horsejlm@jlu.edu.cn

ywyang@jlu.edu.cn

Received Date: 25 July 2020
Revised Date: 11 August 2020
Accepted Date: 18 August 2020
Available Online: 22 August 2020

Figures(4)

Smart strategies that can decrease the side effect and enhance the therapeutic efficacy of chemotherapy are in urgent need to meet the special demands of cancer therapy. Herein, two water-soluble macrocyclic hosts, i. e., a carboxylated leaning tower[6]arene (CLT6) and a carboxylated [2]biphenyl-extended pillar[6]arene (CBpP6), are used to load chemotherapy drug oxaliplatin (OxPt) by forming inclusion complexes (OxPt⊂CLT6 and OxPt⊂CBpP6) through host-guest interactions. Interestingly, OxPt can be released from the macrocyclic cavities of these drug delivery systems (DDSs) via the competitive binding effect of spermine (SPM) because of the stronger binding abilities of CLT6/CBpP6 toward SPM as compared with OxPt, leading to enhanced cytotoxicity on SPM-overexpressed cancer cells, such as breast cancer MCF-7 cells. Moreover, compared to free OxPt, due to the low concentration of SPM in normal cells, OxPt⊂CLT6 and OxPt⊂CBpP6 demonstrated a decreased cytotoxicity on liver L02 cells, which is beneficial for reducing the side effect of anticancer drug during chemotherapy. Such a strategy might be extended to other antitumor drugs and water-soluble macrocycles with suitable cavity sizes to achieve controllable drug delivery and enhanced anticancer ability in supramolecular chemotherapy.
- Drug delivery system,
- Host-guest chemistry,
- Macrocyclic chemistry,
- Supramolecular chemotherapy,
- Supramolecular chemistry
1. [1]
  W.Q. Lim, G. Yang, S.Z.F. Phua, H. Chen, Y. Zhao, ACS Appl. Mater. Interfaces 11 (2019) 16391-16401. doi: 10.1021/acsami.9b04557
2. [2]
  T. Sun, Y.S. Zhang, B. Pang, et al., Angew. Chem. Int. Ed. 53 (2014) 12320-12364.
3. [3]
  J. Zhou, G. Yu, F. Huang, Chem. Soc. Rev. 46 (2017) 7021-7053. doi: 10.1039/C6CS00898D
4. [4]
  M.W. Tibbitt, J.E. Dahlman, R. Langer, J. Am. Chem. Soc. 138 (2016) 704-717. doi: 10.1021/jacs.5b09974
5. [5]
  M. Karimi, P. Sahandi Zangabad, S. Baghaee-Ravari, et al., J. Am. Chem. Soc. 139 (2017) 4584-4610. doi: 10.1021/jacs.6b08313
6. [6]
  S.S. Said, S. Campbell, T. Hoare, Chem. Mater. 31 (2019) 4971-4989. doi: 10.1021/acs.chemmater.9b01798
7. [7]
  M.X. Wu, Y.W. Yang, Adv. Mater. 29 (2017) 1606134. doi: 10.1002/adma.201606134
8. [8]
  N. Zhao, L. Yan, X. Zhao, et al., Chem. Rev. 119 (2019) 1666-1762. doi: 10.1021/acs.chemrev.8b00401
9. [9]
  Q. Hu, H. Li, L. Wang, H. Gu, C. Fan, Chem. Rev. 119 (2019) 6459-6506.
10. [10]
  J. Yang, Y.W. Yang, Small 16 (2020) 1906846. doi: 10.1002/smll.201906846
11. [11]
  J.A. Barreto, W. O'Malley, M. Kubeil, et al., Adv. Mater. 23 (2011) H18-H40. doi: 10.1002/adma.201100140
12. [12]
  J. Yang, Y.W. Yang, View 1 (2020) e20.
13. [13]
  X. Wang, M. Li, K. Ren, et al., Adv. Mater. 32 (2020) 2002160. doi: 10.1002/adma.202002160
14. [14]
  K. Zhu, Y. Ju, J. Xu, et al., Acc. Chem. Res. 51 (2018) 404-413. doi: 10.1021/acs.accounts.7b00407
15. [15]
  G. Yang, S.Z.F. Phua, A.K. Bindra, Y. Zhao, Adv. Mater. 31 (2019) 1805730. doi: 10.1002/adma.201805730
16. [16]
  F. Tang, L. Li, D. Chen, Adv. Mater. 24 (2012) 1504-1534. doi: 10.1002/adma.201104763
17. [17]
  G. Yu, X. Zhao, J. Zhou, et al., J. Am. Chem. Soc. 140 (2018) 8005-8019. doi: 10.1021/jacs.8b04400
18. [18]
  X. Li, H. Bai, Y. Yang, et al., Adv. Mater. 31 (2019) 1805092.
19. [19]
  S. Aryal, C.M.J. Hu, L. Zhang, ACS Nano 4 (2010) 251-258. doi: 10.1021/nn9014032
20. [20]
  S.Z.F. Phua, C. Xue, W.Q. Lim, et al., Chem. Mater. 31 (2019) 3349-3358. doi: 10.1021/acs.chemmater.9b00439
21. [21]
  Z. Zheng, W.C. Geng, Z. Xu, D.S. Guo, Isr. J. Chem. 59 (2019) 913-927. doi: 10.1002/ijch.201900032
22. [22]
  M.J. Webber, R. Langer, Chem. Soc. Rev. 46 (2017) 6600-6620. doi: 10.1039/C7CS00391A
23. [23]
  T. Ogoshi, T. Kakuta, T.A. Yamagishi, Angew. Chem. Int. Ed. 58 (2019) 2197-2206. doi: 10.1002/anie.201805884
24. [24]
  D. Xia, P. Wang, X. Ji, et al., Chem. Rev. 120 (2020) 6070-6123. doi: 10.1021/acs.chemrev.9b00839
25. [25]
  N. Song, T. Kakuta, T.A. Yamagishi, Y.W. Yang, T. Ogoshi, Chem 4 (2018) 2029-2053. doi: 10.1016/j.chempr.2018.05.015
26. [26]
  L. Liang, Y. Chen, X.M. Chen, Y. Zhang, Y. Liu, Chin. Chem. Lett. 29 (2018) 989-991. doi: 10.1016/j.cclet.2017.12.022
27. [27]
  L.L. Tan, H. Li, Y. Tao, et al., Adv. Mater. 26 (2014) 7027-7031. doi: 10.1002/adma.201401672
28. [28]
  L.L. Tan, Y. Zhu, Y. Jin, W. Zhang, Y.W. Yang, Supramol. Chem. 30 (2018) 648-654. doi: 10.1080/10610278.2018.1427239
29. [29]
  D. Dai, Z. Li, J. Yang, et al., J. Am. Chem. Soc. 141 (2019) 4756-4763. doi: 10.1021/jacs.9b01546
30. [30]
  M.X. Wu, Y.W. Yang, Polym. Chem. 10 (2019) 2980-2985. doi: 10.1039/C8PY01497C
31. [31]
  X. Wang, Z.J. Liu, E.H. Hill, et al., Matter 1 (2019) 848-861. doi: 10.1016/j.matt.2019.03.005
32. [32]
  X. Wang, J.R. Wu, F. Liang, Y.W. Yang, Org. Lett. 21 (2019) 5215-5218. doi: 10.1021/acs.orglett.9b01827
33. [33]
  H. Yao, Q. Zhou, Y. Zhang, et al., Chin. Chem. Lett. 31 (2020) 1231-1234. doi: 10.1016/j.cclet.2019.09.046
34. [34]
  N. Song, X.Y. Lou, H. Yu, et al., Mater. Chem. Front. 4 (2020) 950-956. doi: 10.1039/C9QM00741E
35. [35]
  Z. Liu, J.R. Wu, C. Wang, et al., Chin. Chem. Lett. 30 (2019) 2299-2303. doi: 10.1016/j.cclet.2019.10.023
36. [36]
  P. Li, Y. Chen, Y. Liu, Chin. Chem. Lett. 30 (2019) 1190-1197. doi: 10.1016/j.cclet.2019.03.035
37. [37]
  H.B. Cheng, Y.M. Zhang, Y. Liu, J. Yoon, Chem 5 (2019) 553-574. doi: 10.1016/j.chempr.2018.12.024
38. [38]
  X.Y. Lou, Y.P. Li, Y.W. Yang, Biotechnol. J. 14 (2018) 1800354.
39. [39]
  M.X. Wu, J. Gao, F. Wang, et al., Small 14 (2018) 1704440. doi: 10.1002/smll.201704440
40. [40]
  Q.L. Li, Y. Sun, L. Ren, et al., ACS Appl. Mater. Interfaces 10 (2018) 29314-29324. doi: 10.1021/acsami.8b09330
41. [41]
  J. Yang, D. Dai, X. Lou, et al., Theranostics 10 (2020) 615-629. doi: 10.7150/thno.40066
42. [42]
  Y. Chen, S. Sun, D. Lu, Y. Shi, Y. Yao, Chin. Chem. Lett. 30 (2019) 37-43. doi: 10.1016/j.cclet.2018.10.022
43. [43]
  T. Ogoshi, S. Kanai, S. Fujinami, T.A. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc. 130 (2008) 5022-5023. doi: 10.1021/ja711260m
44. [44]
  T. Ogoshi, T.A. Yamagishi, Y. Nakamoto, Chem. Rev. 116 (2016) 7937-8002. doi: 10.1021/acs.chemrev.5b00765
45. [45]
  T. Ogoshi, N. Ueshima, F. Sakakibara, T.A. Yamagishi, T. Haino, Org. Lett. 16 (2014) 2896-2899. doi: 10.1021/ol501039u
46. [46]
  X.B. Hu, Z. Chen, L. Chen, et al., Chem. Commun. 48 (2012) 10999-11001. doi: 10.1039/c2cc36027f
47. [47]
  Y. Chen, H.Q. Tao, Y.H. Kou, et al., Chin. Chem. Lett. 23 (2012) 509-511. doi: 10.1016/j.cclet.2012.03.026
48. [48]
  B. Li, Z. Meng, Q. Li, et al., Chem. Sci. 8 (2017) 4458-4464. doi: 10.1039/C7SC01438D
49. [49]
  N. Song, X.Y. Lou, L. Ma, H. Gao, Y.W. Yang, Theranostics 9 (2019) 3075-3093. doi: 10.7150/thno.31858
50. [50]
  X.Y. Lou, Y.W. Yang, Adv. Mater. 32 (2020) 2003263. doi: 10.1002/adma.202003263
51. [51]
  Y. Cao, X.Y. Hu, Y. Li, et al., J. Am. Chem. Soc. 136 (2014) 10762-10769. doi: 10.1021/ja505344t
52. [52]
  X. Li, J. Han, X. Wang, et al., Mater. Chem. Front. 3 (2019) 103-110. doi: 10.1039/C8QM00509E
53. [53]
  K. Jie, M. Liu, Y. Zhou, et al., J. Am. Chem. Soc. 139 (2017) 2908-2911. doi: 10.1021/jacs.6b13300
54. [54]
  J.R. Wu, Y.W. Yang, Chem. Commun. 55 (2019) 1533-1543. doi: 10.1039/C8CC09374A
55. [55]
  B. Gao, L.L. Tan, N. Song, K. Li, Y.W. Yang, Chem. Commun. 52 (2016) 5804-5807. doi: 10.1039/C6CC01892K
56. [56]
  J.R. Wu, C.Y. Wang, Y.C. Tao, et al., Eur. J. Org. Chem. 2018 (2018) 1321-1325. doi: 10.1002/ejoc.201800112
57. [57]
  J.R. Wu, A.U. Mu, B. Li, et al., Angew. Chem. Int. Ed. 57 (2018) 9853-9858. doi: 10.1002/anie.201805980
58. [58]
  D. Xia, Y. Li, K. Jie, B. Shi, Y. Yao, Org. Lett. 18 (2016) 2910-2913. doi: 10.1021/acs.orglett.6b01264
59. [59]
  T. Ogoshi, M. Hashizume, T.A. Yamagishi, Y. Nakamoto, Chem. Commun. 46 (2010) 3708-3710. doi: 10.1039/c0cc00348d
60. [60]
  G. Yu, M. Xue, Z. Zhang, et al., J. Am. Chem. Soc. 134 (2012) 13248-13251. doi: 10.1021/ja306399f
61. [61]
  W.H. Chen, W.C. Liao, Y.S. Sohn, et al., Adv. Funct. Mater. 28 (2018) 1705137. doi: 10.1002/adfm.201705137
62. [62]
  Z. He, X. Huang, C. Wang, et al., Angew. Chem. Int. Ed. 58 (2019) 8752-8756. doi: 10.1002/anie.201902612
63. [63]
  Y. Wang, J. Yan, N. Wen, et al., Biomaterials 230 (2020) 119619. doi: 10.1016/j.biomaterials.2019.119619
64. [64]
  Y. Chen, Z. Huang, J.F. Xu, Z. Sun, X. Zhang, ACS Appl. Mater. Interfaces 8 (2016) 22780-22784. doi: 10.1021/acsami.6b08295
65. [65]
  J. Chen, H. Ni, Z. Meng, et al., Nat. Commun. 10 (2019) 3546. doi: 10.1038/s41467-019-11553-7
66. [66]
  C. Sun, H. Zhang, S. Li, et al., ACS Appl. Mater. Interfaces 10 (2018) 25090-25098. doi: 10.1021/acsami.8b06598
67. [67]
  L. Yue, C. Sun, C.H.T. Kwong, R. Wang, J. Mater. Chem. B 8 (2020) 2749-2753. doi: 10.1039/D0TB00306A
68. [68]
  Y.F. Ding, J. Wei, S. Li, et al., ACS Appl. Mater. Interfaces 11 (2019) 28665-28670. doi: 10.1021/acsami.9b09059
69. [69]
  L. Yue, C. Sun, Q. Cheng, et al., Chem. Commun. 55 (2019) 13506-13509. doi: 10.1039/C9CC07131H
70. [70]
  Q. Cheng, K.X. Teng, Y.F. Ding, et al., Chem. Commun. 55 (2019) 2340-2343. doi: 10.1039/C8CC09432B
71. [71]
  Q. Hao, Y. Chen, Z. Huang, et al., ACS Appl. Mater. Interfaces 10 (2018) 5365-5372. doi: 10.1021/acsami.7b19784
1. [1]
  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
2. [2]
  Xuanyu Wang , Zhao Gao , Wei Tian . Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction. Chinese Chemical Letters, 2024, 35(11): 109757-. doi: 10.1016/j.cclet.2024.109757
3. [3]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
4. [4]
  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
5. [5]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
6. [6]
  Jiarui Wu , Gengxin Wu , Yan Wang , Yingwei Yang . Crystal Engineering Based on Leaning Towerarenes. University Chemistry, 2024, 39(3): 58-62. doi: 10.3866/PKU.DXHX202304014
7. [7]
  Yujie Li , Ya-Nan Wang , Yin-Gen Luo , Hongcai Yang , Jinrui Ren , Xiao Li . Advances in synthetic biology-based drug delivery systems for disease treatment. Chinese Chemical Letters, 2024, 35(11): 109576-. doi: 10.1016/j.cclet.2024.109576
8. [8]
  Qiang Li , Jiangbo Fan , Hongkai Mu , Lin Chen , Yongzhen Yang , Shiping Yu . Nucleus-targeting orange-emissive carbon dots delivery adriamycin for enhanced anti-liver cancer therapy. Chinese Chemical Letters, 2024, 35(6): 108947-. doi: 10.1016/j.cclet.2023.108947
9. [9]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362
10. [10]
  Dan Luo , Jinya Tian , Jianqiao Zhou , Xiaodong Chi . Anthracene-bridged "Texas-sized" box for the simultaneous detection and uptake of tryptophan. Chinese Chemical Letters, 2024, 35(9): 109444-. doi: 10.1016/j.cclet.2023.109444
11. [11]
  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
12. [12]
  Yanfei Liu , Yaqin Hu , Yifu Tan , Qiwen Chen , Zhenbao Liu . Tumor acidic microenvironment activatable DNA nanostructure for precise cancer cell targeting and inhibition. Chinese Chemical Letters, 2025, 36(1): 110289-. doi: 10.1016/j.cclet.2024.110289
13. [13]
  Kang Wei , Jiayu Li , Wen Zhang , Bing Yuan , Ming-De Li , Pingwu Du . A strained π-extended [10]cycloparaphenylene carbon nanoring. Chinese Chemical Letters, 2024, 35(5): 109055-. doi: 10.1016/j.cclet.2023.109055
14. [14]
  Junying Zhang , Ruochen Li , Haihua Wang , Wenbing Kang , Xing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216
15. [15]
  Zhimin Sun , Xin-Hui Guo , Yue Zhao , Qing-Yu Meng , Li-Juan Xing , He-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162
16. [16]
  Zixi Zou , Jingyuan Wang , Yian Sun , Qian Wang , Da-Hui Qu . Controlling molecular assembly on time scale: Time-dependent multicolor fluorescence for information encryption. Chinese Chemical Letters, 2024, 35(7): 108972-. doi: 10.1016/j.cclet.2023.108972
17. [17]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
18. [18]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
19. [19]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1108)
HTML views(116)

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