Citation: 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[J]. Chinese Chemical Letters, ;2025, 36(1): 109752. doi: 10.1016/j.cclet.2024.109752 shu

A supramolecular formulation of icariin@sulfonatoazocalixarene for hypoxia-targeted osteoarthritis therapy

Chao Zhang ^{a, b, 1} ,
Ai-Feng Liu ^{a, b, 1} ,
Shihui Li ^{c, 1} ,
Fang-Yuan Chen ^c ,
Jun-Tao Zhang ^{a, b} ,
Fang-Xing Zeng ^{a, b} ,
Hui-Chuan Feng ^{a, b} ,
Ping Wang ^{a, b} ,
Wen-Chao Geng ^{c, *,} ,
Chuan-Rui Ma ^{a, b, *,} ,
Dong-Sheng Guo ^{c, *,}

a.
Orthopedics department, First Teaching Hospital of Tianjin University of Traditional Chinese Medicine, Tianjin 300380, China
b.
Orthopedics department, National Clinical Research Center for Chinese Medicine Acupuncture and Moxibustion, Tianjin 300380, China
c.
College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China

wchgeng@nankai.edu.cn

mcr2013@qq.com

dshguo@nankai.edu.cn

Received Date: 28 December 2023
Revised Date: 25 February 2024
Accepted Date: 5 March 2024
Available Online: 11 March 2024

Figures(4)

Osteoarthritis (OA) is the most prevalent joint disease and icariin is a promising drug for its treatment. However, the clinical use of icariin is hindered by poor water solubility, low bioavailability, and non-specific release and biological distribution. Herein, sulfonated azocalix[4]arene (SAC4A) with enhanced water solubility, recognition capacity, and designed responsiveness was used to improve the efficiency of icariin for OA therapy. SAC4A, a macrocycle with well-defined molecular weight and structure, could encapsulate and enhance water solubility of various drugs. In addition, SAC4A enables hypoxia-responsive release of loaded drug. Compared with icariin treatment, supramolecular complex icariin@SAC4A significantly relieved OA symptoms of rats, including more regular bone morphology and structure, and lower degree of cartilage damage. Moreover, the supramolecular formulation demonstrated various advantages, including easy preparation, hypoxia-triggered release, and small size that conducive to drug penetration.
- Biomaterial,
- Supramolecular chemistry,
- Calixarene,
- Icariin,
- Osteoarthritis
1. [1]
  D.J. Hunter, S. Bierma-Zeinstra, Lancet 393 (2019) 1745–1759. doi: 10.1016/S0140-6736(19)30417-9
2. [2]
  L. Sharma, New Engl. J. Med. 384 (2021) 51–59. doi: 10.1056/nejmcp1903768
3. [3]
  D. Chen, J. Shen, W. Zhao, et al., Bone Res. 5 (2017) 16044. doi: 10.1038/boneres.2016.44
4. [4]
  V. Francisco, J. Pino, M.Á. González-Gay, et al., Nat. Rev. Rheumatol. 18 (2022) 47–60. doi: 10.1038/s41584-021-00713-z
5. [5]
  H. Yin, M. Li, G. Tian, et al., Biomater. Res. 26 (2022) 52. doi: 10.1186/s40824-022-00300-7
6. [6]
  F. Xiong, Z. Qin, H. Chen, et al., J. Nanobiotechnol. 18 (2020) 139. doi: 10.1186/s12951-020-00694-3
7. [7]
  Z. Li, M. Li, P. Xu, et al., Cell Transplant 29 (2020) 1–10.
8. [8]
  C.Y. Zeng, X.F. Wang, et al., Front. Pharmacol. 13 (2022) 927126. doi: 10.3389/fphar.2022.927126
9. [9]
  M. Kloppenburg, F. Berenbaum, Osteoarthr. Cartilage. 28 (2020) 242–248. doi: 10.1016/j.joca.2020.01.002
10. [10]
  L.J. Crofford, Arthritis Res. Ther. 15 (2013) S2.
11. [11]
  J. Zhang, F. Fan, A. Liu, et al., Front. Pharmacol. 13 (2022) 81108.
12. [12]
  D. Li, T. Yuan, X. Zhang, et al., Osteoarthr. Cartilage. 20 (2012) 1647–1656. doi: 10.1016/j.joca.2012.08.009
13. [13]
  X. Li, Y. Xu, H. Li, et al., Biomed. Pharmacother. 144 (2021) 112259. doi: 10.1016/j.biopha.2021.112259
14. [14]
  Y. Zhu, L. Ye, X. Cai, et al., Front. Bioeng. Biotech. 10 (2022) 755260. doi: 10.3389/fbioe.2022.755260
15. [15]
  X. Sun, J. Wei, J. Lyu, et al., J. Nanobiotech. 17 (2019) 10. doi: 10.1186/s12951-019-0447-5
16. [16]
  X. Zhang, T. Liu, Y. Huang, et al., Phytother. Res. 28 (2014) 498–509. doi: 10.1002/ptr.5027
17. [17]
  Z. Luo, X. Chen, M. Liu, et al., Mater. Design 200 (2021) 109468. doi: 10.1016/j.matdes.2021.109468
18. [18]
  D. Xu, Y.R. Lu, N. Kou, et al., Int. J. Pharmaceut. 586 (2020) 119550. doi: 10.1016/j.ijpharm.2020.119550
19. [19]
  R. Szabó, C.P. Rácz, F.V. Dulf, Int. J. Mol. Sci. 23 (2022) 7519. doi: 10.3390/ijms23147519
20. [20]
  R. Yan, Y. Guo, X. Wang, et al., ACS Nano 16 (2022) 8399–8418. doi: 10.1021/acsnano.2c02900
21. [21]
  M. Liu, B. Wang, C. Guo, et al., Drug Deliv. 26 (2019) 1002–1016. doi: 10.1080/10717544.2019.1669734
22. [22]
  A.M. Negrescu, V. Mitran, W. Draghicescu, et al., J. Funct. Biomater. 13 (2022) 43. doi: 10.3390/jfb13020043
23. [23]
  X. Song, K. Gan, S. Qin, et al., Sci. Rep. 9 (2019) 6365. doi: 10.1038/s41598-019-42909-0
24. [24]
  M. Dong, S. Wu, H. Xu, et al., Front. Bioeng. Biotech. 9 (2021) 615920. doi: 10.3389/fbioe.2021.615920
25. [25]
  X. Hou, X. Zhang, W. Zhao, et al., Nat. Nanotechnol. 15 (2020) 41–46. doi: 10.1038/s41565-019-0600-1
26. [26]
  S. Li, R. Ma, X.Y. Hu, et al., Adv. Mater. 34 (2022) e2203765. doi: 10.1002/adma.202203765
27. [27]
  M.J. Webber, R. Langer, Chem. Soc. Rev. 46 (2017) 6600–6620. doi: 10.1039/C7CS00391A
28. [28]
  P. Liu, D. Li, M. Kang, et al., Small Struct. 4 (2023) 2200329. doi: 10.1002/sstr.202200329
29. [29]
  B. Hazarika, V.P. Singh, Chin. Chem. Lett. 34 (2023) 108220. doi: 10.1016/j.cclet.2023.108220
30. [30]
  J. Chen, Y. Zhang, Y. Zhang, et al., Chin. Chem. Lett. 32 (2021) 3034–3038. doi: 10.1016/j.cclet.2021.03.079
31. [31]
  G. Yu, X. Chen, Theranostics 9 (2019) 3041–3074. doi: 10.7150/thno.31653
32. [32]
  J. Gao, J. Li, W.C. Geng, et al., J. Am. Chem. Soc. 140 (2018) 4945–4953. doi: 10.1021/jacs.8b02331
33. [33]
  L. Xu, Y. Chen, Q. Jin, et al., Small Struct. 4 (2023) 2300004. doi: 10.1002/sstr.202300004
34. [34]
  S. Li, Y. Gao, Y. Ding, et al., Chin. Chem. Lett. 32 (2021) 313–318. doi: 10.1016/j.cclet.2020.04.049
35. [35]
  A.S. Braegelman, M.J. Webber, Theranostics 9 (2019) 3017–3040. doi: 10.7150/thno.31913
36. [36]
  S. Wang, Y. Duan, Q. Zhang, et al., Small Struct. 1 (2020) 2000018. doi: 10.1002/sstr.202000018
37. [37]
  X.Y. Hu, J. Gao, F.Y. Chen, et al., J. Control. Release 324 (2020) 124–133. doi: 10.1016/j.jconrel.2020.05.008
38. [38]
  Y. Zhang, Y. Wang, T. Chen, et al., Chem. Commun. 59 (2023) 8266–8269. doi: 10.1039/d3cc01929b
39. [39]
  T. Chen, J. Wang, R. Tang, et al., Chin. Chem. Lett. 34 (2023) 108088. doi: 10.1016/j.cclet.2022.108088
40. [40]
  H. Guo, X. Yan, B. Lu, et al., J. Mater. Chem. C 8 (2020) 15622–15625. doi: 10.1039/d0tc04343e
41. [41]
  J. Zhou, L. Rao, G. Yu, et al., Chem. Soc. Rev. 50 (2021) 2839–2891. doi: 10.1039/d0cs00011f
42. [42]
  G. Yu, K. Jie, F. Huang, Chem. Rev. 115 (2015) 7240–7303. doi: 10.1021/cr5005315
43. [43]
  Y.M. Zhang, Y.H. Liu, Y. Liu, Adv. Mater. 32 (2020) 1806158. doi: 10.1002/adma.201806158
44. [44]
  Q.D. Hu, G.P. Tang, P.K. Chu, Acc. Chem. Res. 47 (2014) 2017–2025. doi: 10.1021/ar500055s
45. [45]
  Q. Huang, Z.Y. Hu, S. Guo, et al., Supramol. Chem. (2022) 100020.
46. [46]
  J.J. Wu, F.Y. Chen, B.B. Han, et al., CCS Chem. 5 (2023) 885–901. doi: 10.31635/ccschem.022.202201859
47. [47]
  F.Y. Chen, W.C. Geng, K. Cai, et al., Chin. Chem. Lett. 35 (2024) 109161. doi: 10.1016/j.cclet.2023.109161
48. [48]
  T. Lu, Q. Chen, J. Comput. Chem. 43 (2022) 539–555. doi: 10.1002/jcc.26812
49. [49]
  T. Lu, F. Chen, J. Comput. Chem. 33 (2012) 580–592. doi: 10.1002/jcc.22885
50. [50]
  T. Yanai, D.P. Tew, N.C. Handy, Chem. Phys. Lett. 393 (2004) 51–57. doi: 10.1016/j.cplett.2004.06.011
51. [51]
  T.X. Zhang, X. Hou, Y. Kong, et al., Theranostics 12 (2022) 396–409. doi: 10.7150/thno.67036
52. [52]
  Z. Liu, X. Fu, Y. Chen, et al., China Pharmacist 12 (2009) 5–8.
53. [53]
  T. Gui, Y. Wei, L. Luo, et al., J. Bone Miner. Res. 37 (2022) 2498–2511.
54. [54]
  Y.X. Yue, Z. Zhang, Z.H. Wang, Small Struct. 3 (2022) 2200067. doi: 10.1002/sstr.202200067
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  Ling Zhang , Jing Kang . Turn Waste into Valuable: Preparation of High-Strength Water-Based Adhesives from Polymethylmethacrylate Wastes: a Comprehensive Chemical Experiments. University Chemistry, 2024, 39(2): 221-226. doi: 10.3866/PKU.DXHX202306075
12. [12]
  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
13. [13]
  Yang Xu , Le Ma , Yang Wang , Chunmeng Shi . Engineering strategies of biomaterial-assisted exosomes for skin wound repair: Latest advances and challenges. Chinese Chemical Letters, 2025, 36(1): 109766-. doi: 10.1016/j.cclet.2024.109766
14. [14]
  Hui Liu , Xi Xiang , Jian-Bo Huang , Bi-Hui Zhu , Li-Yun Wang , Yuan-Jiao Tang , Fang-Xue Du , Ling Li , Feng Yan , Lang Ma , Li Qiu . Corrigendum to "Ultrasound augmenting injectable chemotaxis hydrogel for articular cartilage repair in osteoarthritis" [Chinese Chemical Letters 32 (2021) 1759-1764]. Chinese Chemical Letters, 2025, 36(2): 110562-. doi: 10.1016/j.cclet.2024.110562
15. [15]
  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
16. [16]
  Peiwen Liu , Fang Zhao , Jing Zhang , Yunpeng Bai , Jinxing Ye , Bo Bao , Xinggui Zhou , Li Zhang , Changlu Zhou , Xinhai Yu , Peng Zuo , Jianye Xia , Lian Cen , Yangyang Yang , Guoyue Shi , Lin Xu , Weiping Zhu , Yufang Xu , Xuhong Qian . Micro/nano flow chemistry by Beyond Limits Manufacturing. Chinese Chemical Letters, 2024, 35(5): 109020-. doi: 10.1016/j.cclet.2023.109020
17. [17]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
18. [18]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Qiang Sun , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Li Wang . Recent progress on surface chemistry Ⅱ: Property and characterization. Chinese Chemical Letters, 2025, 36(1): 110100-. doi: 10.1016/j.cclet.2024.110100
19. [19]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
20. [20]
  Xiangjun Zhang , Xiaodi Yang , Yan Wang , Zhongping Xu , Sisi Yi , Tao Guo , Yue Liao , Xiyu Tang , Jianxiang Zhang , Ruibing Wang . A supramolecular nanoprodrug for prevention of gallstone formation. Chinese Chemical Letters, 2025, 36(2): 109854-. doi: 10.1016/j.cclet.2024.109854

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(110)
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