Citation: Wang Zhang, Ping Xiao, Liwei Lin, Fang Guo, Qingyue Wang, Yuanzhe Piao, Guowang Diao. Study of a water-soluble supramolecular complex of curcumin and β-cyclodextrin polymer with electrochemical property and potential anti-cancer activity[J]. Chinese Chemical Letters, ;2022, 33(8): 4043-4047. doi: 10.1016/j.cclet.2021.12.037 shu

Study of a water-soluble supramolecular complex of curcumin and β-cyclodextrin polymer with electrochemical property and potential anti-cancer activity

Wang Zhang ^{a, *,} ,
Ping Xiao ^{a, 1} ,
Liwei Lin ^{b, 1} ,
Fang Guo ^a ,
Qingyue Wang ^c ,
Yuanzhe Piao ^{b, d, *,} ,
Guowang Diao ^{a, *,}

a.
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China
b.
Department of Applied Bioengineering, Graduate School of Convergence Science and Technology, Seoul National University, Suwon 443-270, Republic of Korea
c.
Shanghai Suni Biotechnology Development Co., Ltd., Shanghai 201300, China
d.
Advanced Institutes of Convergence Technology, Suwon 443-270, Republic of Korea

zhangwang@yzu.edu.cn

parkat9@snu.ac.kr

gwdiao@yzu.edu.cn

Received Date: 14 September 2021
Revised Date: 9 December 2021
Accepted Date: 14 December 2021
Available Online: 20 December 2021

Figures(3)

As a member of the curcuminoid compound family, curcumin (Cur) has many interesting therapeutic properties. However, its low aqueous solubility and stability have resulted in poor bioavailability and restricted clinical efficacy. Based on size matching, β-cyclodextrin polymer (β-CDP), with its hydrophilic polymer chains and hydrophobic cavities, can form an inclusion complex with Cur. To improve the water solubility and stability of Cur, a simple and eco-friendly grinding method was designed to form β-CDP inclusion complexes. According to the Boltzmann–Hamel's method and Job's method, the molar ratio of the β-CD unit in β-CDP to Cur was determined to be 1 : 1. The diffusion coefficient and diffusion activation energy of Cur-β-CDP were calculated in an electrochemical study. This supramolecular complex worked well in vitro to inhibit the proliferation of hepatoma carcinoma cells HepG2. Remarkably, this method visibly reduced the undesirable side effects on normal cells, without weakening the anti-cancer activity of the drugs. We expect that the obtained host–guest complex will provide a new approach for delivering natural drug molecules, having low water solubility.
- Cyclodextrin polymer,
- Curcumin,
- Solubility,
- Anti-cancer activity,
- Supramolecular complex
1. [1]
  Z. Stanić, Curcumin, Plant Foods Hum. Nutr.72 (2017) 1–12. doi: 10.1007/s11130-016-0590-1
2. [2]
  M.C. Fadus, C. Lau, J. Bikhchandani, H.T. Lynch, J. Tradit. Complement. Med. 7 (2017) 339–346. doi: 10.1016/j.jtcme.2016.08.002
3. [3]
  L. Chen, C. Hu, M. Hood, et al., Nutrients 12 (2020) 1193. doi: 10.3390/nu12041193
4. [4]
  Y. Xi, J. Ge, M. Wang, et al., ACS Nano 14 (2020) 2904–2916. doi: 10.1021/acsnano.9b07173
5. [5]
  D.N.K. Reddy, F.Y. Huang, S.P. Wang, R. Kumar, Curr. Pharm. Design 26 (2020) 5021–5029. doi: 10.2174/1381612826666200609164830
6. [6]
  M. Kharat, M. Skrzynski, E.A. Decker, D.J. McClements, Food Chem. 320 (2020) 126653. doi: 10.1016/j.foodchem.2020.126653
7. [7]
  K. Jakubczyk, A. Drużga, J. Katarzyna, K. Skonieczna-Żydecka, Antioxidants 9 (2020) 1092. doi: 10.3390/antiox9111092
8. [8]
  A. De, D.H. Beligala, T.M. Birkholz, M.E. Geusz, Integr. Cancer Ther. 18 (2019) 1–10. doi: 10.1158/1535-7163.1.18.1
9. [9]
  X.S. Wang, Z.R. Zhang, M.M. Zhang, et al., BMC Complement Altern. Med. 17 (2017) 412. doi: 10.1186/s12906-017-1922-x
10. [10]
  M.K. Jeenger, S. Shrivastava, V.G. Yerra, et al., Nutrition 31 (2015) 276–282. doi: 10.1016/j.nut.2014.06.015
11. [11]
  M. Rai, R. Pandit, S. Gaikwad, et al., Nanotechnol. Rev. 4 (2015) 161–172.
12. [12]
  M. Moballegh Nasery, B. Abadi, D. Poormoghadam, et al., Molecules 25 (2020) 689. doi: 10.3390/molecules25030689
13. [13]
  S. Afrin, F. Giampieri, M. Gasparrini, et al., Biotechnol. Adv. 38 (2020) 107322.
14. [14]
  Z. Ma, N. Wang, H. He, X. Tang, J. Controlled Release 316 (2019) 359–380. doi: 10.1016/j.jconrel.2019.10.053
15. [15]
  M. Ghazaeian, K. Khorsandi, R. Hosseinzadeh, et al., J. Biomol. Struct. Dyn. 39 (2021) 6606–6616. doi: 10.1080/07391102.2020.1802342
16. [16]
  R. Jamwal, J. Integrative Med. 16 (2018) 367–374. doi: 10.1016/j.joim.2018.07.001
17. [17]
  E.M.M. Del Valle, Process Biochem. 39 (2004) 1033–1046. doi: 10.1016/S0032-9592(03)00258-9
18. [18]
  T. Kuwabara, Y. Hosokawa, J. Hu, T. Ide, J. Incl. Phenom. Macrocycl. Chem. 93 (2019) 85–90. doi: 10.1007/s10847-018-0845-6
19. [19]
  J. Wankar, N.G. Kotla, S. Gera, et al., Adv. Funct. Mater. 30 (2020) 1909049. doi: 10.1002/adfm.201909049
20. [20]
  P. de Vos, M.M. Faas, M. Spasojevic, J. Sikkema, Int. Dairy J. 20 (2010) 292–302. doi: 10.1016/j.idairyj.2009.11.008
21. [21]
  Y. Liu, D.E. Sameen, S. Ahmed, et al., Food Chem. 370 (2022) 131026. doi: 10.1016/j.foodchem.2021.131026
22. [22]
  M.E. Davis, M.E. Brewster, Nat. Rev. Drug Discov. 3 (2004) 1023–1035. doi: 10.1038/nrd1576
23. [23]
  D. Jia, X. Ma, Y. Lu, et al., Chin. Chem. Lett. 32 (2021) 162–167. doi: 10.1016/j.cclet.2020.11.052
24. [24]
  F. Madrid, M. Rubio-Bellido, E. Morillo, Sci. Total Environ. 715 (2020) 136986.
25. [25]
  G. Crini, Prog. Polym. Sci. 30 (2005) 38–70.
26. [26]
  Y. Zhou, J. Lu, Y. Zhou, Y. Liu, Environ. Pollut. 252 (2019) 352–365. doi: 10.3390/app9020352
27. [27]
  A. Harada, Y. Takashima, H. Yamaguchi, Chem. Soc. Rev. 38 (2009) 875–882. doi: 10.1039/b705458k
28. [28]
  C. Song, Y. Xiao, K. Li, et al., Chin. Chem. Lett. 30 (2019) 1249–1252. doi: 10.1016/j.cclet.2019.03.055
29. [29]
  B. Tian, S. Hua, J. Liu, Carbohydr. Polym. 232 (2020) 115805.
30. [30]
  P. Jansook, N. Ogawa, T. Loftsson, Int. J. Pharm. 535 (2018) 272–284.
31. [31]
  W. Zhang, M. Chen, G. Diao, Electrochim. Acta 56 (2011) 5129–5136.
32. [32]
  B. Zhao, L. Jiang, Q. Jia, Chin. Chem. Lett. 33 (2022) 11–21.
33. [33]
  S. Zohrehvand, C.H. Evans, Polym. Int. 54 (2005) 744–753. doi: 10.1002/pi.1747
34. [34]
  B. Sun, Y. Tian, L. Chen, Z. Jin, Food Hydrocoll. 77 (2018) 911–920.
35. [35]
  C.A. Slabber, C.D. Grimmer, R.S. Robinson, J. Nat. Prod. 79 (2016) 2726–2730. doi: 10.1021/acs.jnatprod.6b00726
36. [36]
  F. Payton, P. Sandusky, W.L. Alworth, J. Nat. Prod. 70 (2007) 143–146. doi: 10.1021/np060263s
37. [37]
  W. Zhang, M. Chen, X. Gong, G. Diao, Carbon N Y 61 (2013) 154–163.
38. [38]
  V. Jahed, A. Zarrabi, A.K. Bordbar, M.S. Hafezi, Food Chem. 165 (2014) 241–246.
39. [39]
  C. Liu, W. Zhang, Q. Wang, et al., Org. Biomol. Chem. 11 (2013) 4993–4999. doi: 10.1039/c3ob40715b
40. [40]
  R. Wimmer, F.L. Aachmann, K.L. Larsen, S.B. Petersen, Carbohydr. Res. 337 (2002) 841–849.
41. [41]
  K.P. Sambasevam, S. Mohamad, N.M. Sarih, N.A. Ismail, Int. J. Mol. Sci. 14 (2013) 3671–3682. doi: 10.3390/ijms14023671
42. [42]
  B. Tang, L. Ma, H.Y. Wang, G.Y. Zhang, J. Agric. Food Chem. 50 (2002) 1355–1361.
43. [43]
  W. Zhang, X. Gong, Y. Cai, et al., Carbohydr. Polym. 95 (2013) 366–370.
44. [44]
  E.J. Olson, P. Bühlmann, J. Org. Chem. 79 (2014) 830-830.
45. [45]
  K. Li, Y. Li, L. Yang, et al., Anal. Methods 6 (2014) 7801–7808. doi: 10.1039/C4AY01492H
46. [46]
  D.M. Wray, C. Batchelor-McAuley, R.G. Compton, Electroanalysis 24 (2012) 2244–2248. doi: 10.1002/elan.201200560
47. [47]
  M. Montiel-Herrera, A. Gandini, F.M. Goycoolea, et al., Carbohydr. Polym. 128 (2015) 220–227.
48. [48]
  Y.Z. Chen, Y.K. Huang, Y. Chen, et al., Chin. Chem. Lett. 26 (2015) 909–913.
49. [49]
  F. Guo, T. Xia, P. Xiao, et al., Bioorg. Chem. 110 (2021) 104764.
50. [50]
  M.S. Gularte, R.F.N. Quadrado, N.S. Pedra, et al., Int. J. Biol. Macromol. 148 (2020) 140–152.
1. [1]
  Ying Xu , Chengying Shen , Hailong Yuan , Wei Wu . Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting. Chinese Chemical Letters, 2024, 35(9): 109324-. doi: 10.1016/j.cclet.2023.109324
2. [2]
  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
3. [3]
  Xiaoman Dang , Zhiying Wu , Tangxin Xiao , Zhouyu Wang , Leyong Wang . Highly robust supramolecular polymer networks crosslinked by metallacycles. Chinese Chemical Letters, 2024, 35(12): 110208-. doi: 10.1016/j.cclet.2024.110208
4. [4]
  Zhe Li , Ping-Zhao Liang , Li Xu , Fei-Yu Yang , Tian-Bing Ren , Lin Yuan , Xia Yin , Xiao-Bing Zhang . Three positive charge nonapoptotic-induced photosensitizer with excellent water solubility for tumor therapy. Chinese Chemical Letters, 2024, 35(8): 109190-. doi: 10.1016/j.cclet.2023.109190
5. [5]
  Lei Zhou , Youjun Zhou , Lizhen Fang , Yiqiao Bai , Yujia Meng , Liang Li , Jie Yang , Yong Yao . Pillar[5]arene based artificial light-harvesting supramolecular polymer for efficient and recyclable photocatalytic applications. Chinese Chemical Letters, 2024, 35(9): 109509-. doi: 10.1016/j.cclet.2024.109509
6. [6]
  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
7. [7]
  Xue-Jiao Wang , Jun-Li Xin , Hong Xiang , Ze-Yu Zhao , Yu-Hang He , Haibo Wang , Guangyao Mei , Yi-Cheng Mao , Juan Xiong , Jin-Feng Hu . Holotrichones A and B, potent anti-leukemic lindenane-type sesquiterpene trimers with unprecedented complex carbon skeletons from a rare Chloranthus species. Chinese Chemical Letters, 2024, 35(12): 109682-. doi: 10.1016/j.cclet.2024.109682
8. [8]
  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
9. [9]
  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
10. [10]
  Siwei Wang , Wei-Lei Zhou , Yong Chen . Cucurbituril and cyclodextrin co-confinement-based multilevel assembly for single-molecule phosphorescence resonance energy transfer behavior. Chinese Chemical Letters, 2024, 35(12): 110261-. doi: 10.1016/j.cclet.2024.110261
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  Wenlong Li , Feishi Shan , Qingdong Bao , Qinghua Li , Hua Gao , Leyong Wang . Supramolecular assembly nanoparticle for trans-epithelial treatment of keratoconus. Chinese Chemical Letters, 2024, 35(10): 110060-. doi: 10.1016/j.cclet.2024.110060
15. [15]
  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
16. [16]
  Chao Ma , Cong Lin , Jian Li . MicroED as a powerful technique for the structure determination of complex porous materials. Chinese Journal of Structural Chemistry, 2024, 43(3): 100209-100209. doi: 10.1016/j.cjsc.2023.100209
17. [17]
  Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
18. [18]
  Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
19. [19]
  Jingwen Zhao , Jianpu Tang , Zhen Cui , Limin Liu , Dayong Yang , Chi Yao . A DNA micro-complex containing polyaptamer for exosome separation and wound healing. Chinese Chemical Letters, 2024, 35(9): 109303-. doi: 10.1016/j.cclet.2023.109303
20. [20]
  Ya-Ping Liu , Zhi-Rong Gui , Zhen-Wen Zhang , Sai-Kang Wang , Wei Lang , Yanzhu Liu , Qian-Yong Cao . A phenylphenthiazide anchored Tb(Ⅲ)-cyclen complex for fluorescent turn-on sensing of ClO⁻. Chinese Chemical Letters, 2025, 36(2): 109769-. doi: 10.1016/j.cclet.2024.109769

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(408)
HTML views(45)

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