Citation: GU Jie, YANG Jun-li, LU Jia-jia, GAO Zhen-jie, YANG Ju, SU Li-Jiao, TAO Xin, YANG Li, YANG Li-Juan. Study on Inclusion Behavior of Sophocarpine with β-Cyclodextrin and Its Derivatives[J]. Chinese Journal of Analytical Chemistry, ;2022, 50(5): 781-790. doi: 10.19756/j.issn.0253-3820.210785 shu

Study on Inclusion Behavior of Sophocarpine with β-Cyclodextrin and Its Derivatives

Key Laboratory of Intelligent Supramolecular Chemistry at the University of Yunnan Province, National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry&Environment, Yunnan Minzu University, Kunming 650500, China

Corresponding author: YANG Li, YANG Li-Juan,
Received Date: 11 October 2021
Revised Date: 31 December 2021

Fund Project: Supported by the National Natural Science Foundation of China (No.21762051), the Program for Innovative Research Team (in Science and Technology) in University of Yunnan Province and Yunnan Provincial Department of Education Science Research Fund Project (No.2020J0315).

By using sophocarpine (SOP) as the guest, and β-cyclodextrin (β-CD), hydroxypropyl-β-cyclodextrin (HP-β-CD), trimethyl-β-cyclodextrin (TM-β-CD), mono-(6-ethanediamine-6- deoxy)-β-cyclodextrin (2N-β-CD) and mono-(6-diethylenetriamine-6- deoxy)-β-cyclodextrin (3N-β-CD) as the host, five host-guest inclusions were prepared by the saturated solution method. The host-guest inclusion complexes were characterized by one-dimensional and two-dimensional nuclear magnetic resonance (¹H NMR, 2D NMR), ultraviolet-visible spectroscopy (UV-Vis), X-ray powder diffraction (XRD) and scanning electron microscopy (SEM). The results showed that the host-guest inclusion ratios of the SOP to the five cyclodextrins were all 1:1. After the formation of inclusion complexes, the water solubility and stability of SOP were obviously increased, and the inclusion compounds were more stable under acidic conditions. Nuclear magnetic resonance analysis showed that the D ring of SOP entered its cavity from the narrow side of the CDs, while the C ring of SOP penetrated the cavity of CDs.
- Sophocarpine,
- β-Cyclodextrin and its derivatives,
- Inclusion behavior,
- Solubility,
- Stability
1. [1]
  LU Y, XU D, LIU J Y, GU L N. Int. Immunopharmacol., 2019, 70:180-186.
2. [2]
  DENG X X, WANG R Z, WU X L, GAO Q X, HAN L, GAO X J, ZHAO S P, CHEN W B, ZHOU R G, LI Z Y, BAI C G. J. Ethnopharmacol., 2019, 248:112172.
3. [3]
  ZHI W B, DU X, LI Y, WANG C L, SUN T T, ZONG S Y, LIU Q Q, HU K, LIU Y, ZHANG H. Int. Immunopharmacol., 2021, 96:107348.
4. [4]
  ZOU F, WANG L, LIU H, WANG W, HU L L, XIONG X Y, WU L J, SHEN Y F, YANG R Q. Front. Pharmacol., 2019, 10:1219.
5. [5]
  SUN X T, YANG Y L, LIU T, HUANG H, KUANG Y, CHEN L. J. Ethnopharmacol., 2021, 273:113998.
6. [6]
  MA Q H, REN M Y, LUO J P. J. Ethnopharmacol., 2021, 264:112800.
7. [7]
  LIU W, ZHANG B L, CHEN G, WU W J, ZHOU L, SHI Y, ZENG Q, LI Y Q, SUN Y W, DENG X M, WANG F. Mol. Ther., 2017, 25(9):2129-2139.
8. [8]
  WANG Q, XU J N, LI X, ZHANG D W, HAN Y, ZHANG X. J. Sep. Sci., 2017, 40(13):2688-2693.
9. [9]
  ZHANG P P, WANG P Q, QIAO C P, ZHANG Q. Cancer. Lett., 2016, 376(1):95-103.
10. [10]
  WANG Q L, WANG T, ZHU L, HE N N, DUAN C Y, DENG W L, ZHANG H P, ZHANG X T. Biol. Pharm. Bull., 2019:42(11):1830-1838.
11. [11]
12. [12]
  LIU Z J, YE L, XI J N, WANG J, FENG Z G. Prog. Polym. Sci., 2021, 118:101408.
13. [13]
  ZHOU J Y, XU H A, TONG Z Z, YANG Y H, JIANG G H. Sci. Eng. Compos. Mater., 2018, 89(8):237-244.
14. [14]
15. [15]
  MOHAMADHOSEINI M, MOHAMADNIA Z. Coord. Chem. Rev., 2020, 432(4):213711.
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
  PRIYA A S, BALAKRISHNAN S B, VEERAKANELLORE G B, STALIN T. J. Mol. Struct., 2018, 1160:1-8.
21. [21]
  JIA S Y, TANG D Y, PENG J, SUN Z J, YANG Y. Carbohydr. Polym., 2019, 208:486-494.
22. [22]
  MOHANDOSS S, EDISON T N J I, ATCHUDAN R, PALANISAMY S, PRABHU N M, NAPOLEON A A, YOU S G, LEE Y R. J. Mol. Liq., 2020, 319:114358.
23. [23]
  KRZAK A, BILEWICZ R. Bioelectrochemistry, 2020, 136:107587.
24. [24]
  SKUREDINA A A, LE-DEYGEN I M, BELOGUROVA N G, KUDRYASHOVA E V. Carbohydr. Res., 2020, 498:108183.
25. [25]
  ROJAS-AGUIRRE Y, TORRES-MENA M A, LÓPE-MÉNDEZ L J, AlCARAZ-ESTRADA S L, GUADARRAMA P, URUCHA-ORT'Z J M. Carbohydr. Polym., 2019, 223:115113.
26. [26]
  LIU Y Y, FAN X D, ZHAO Y B. J. Polym. Sci. Part A:Polym. Chem., 2005, 43(16):3516-3524.
27. [27]
  JIANG H M, YANG H, ZHANG S F. J. Inclusion Phenom. Macrocyclic Chem., 2012, 73(1-4):415-421.
28. [28]
  YANG K, CHANG Y C, WEN J, LU Y C, PEI Y X, CAO S P, WANG F, PEI Z C. Chem. Mater., 2016, 28(7):1990-1993.
29. [29]
  MONTASSIER P, DUCHÊNE D, POELMAN M. C. Int. J. Pharm., 1997, 153(2):199-209.
30. [30]
31. [31]
  CASO J V, RUSSO L, PALMIERI M, MALGIERI G, GALDIERO S, FALANGA A, ISERNIA C, IACOVINO R. Amino Acids, 2015, 47(10):2215-2227.
32. [32]
  MELO C D O, RODRIGUES M S D S, SILVA M V S D, MARCELINO H R, MOURA R O D, OLIVEIRA E E. J. Mol. Struct., 2020:128945.
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