Citation: TAO Xin, ZHANG Jun-Tong, YANG Yun-Han, YANG Ju, SU Li-Jiao, CHEN Yan, YANG Ming-Kun, YANG Li-Juan. Preparation, Characterization and Molecular Modeling Studies of Inclusion Complex of Vincamine With Water-Soluble Phosphate Salt Pillar[6]Arene[J]. Chinese Journal of Analytical Chemistry, ;2023, 51(2): 219-228. doi: 10.19756/j.issn.0253-3820.221469 shu

Preparation, Characterization and Molecular Modeling Studies of Inclusion Complex of Vincamine With Water-Soluble Phosphate Salt Pillar[6]Arene

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

Corresponding author: YANG Li-Juan, yangljyang@sina.com
Received Date: 22 September 2022
Revised Date: 8 December 2022

Fund Project: Supported by the National Natural Science Foundation of China (No. 21762051), the Program for Xingdian Talents (Jiaoxue Mingshi), the Program for Innovative Research Team (in science and technology) in University of Yunnan Province and the Postgraduate Fund (No. 2022SKY031).

A novel host-guest inclusion complex MAA/PP6A was constructed by the saturated solution method with water-soluble phosphate salt pillar[6]arene (PP6A) as the host and the natural medicine maackiain (MAA) as the guest. The preparation process of MAA/PP6A clathrate was screened by orthogonal test with the drug loading of clathrate as an index. The inclusion complex MAA/PP6A was characterized by fluorescence spectroscopy, scanning electron microscope (SEM), X-ray powder diffraction (XRD), and infrared spectroscopy (FT-IR). The inclusion mode of MAA and PP6A inclusion complex was studied by nuclear magnetic resonance spectroscopy (NMR), molecular simulation docking and semi-empirical molecular orbital methods. The results of orthogonal experiments showed that the optimal conditions for the preparation of the inclusion complex were as follows: the mass ratio of PP6A to MAA was 2:1, the volume ratio of ethanol to water was 1:1, and reaction at 50 ℃ for 8 h. Fluorescence spectroscopic titration experiment showed that the inclusion ratio between MAA and PP6A was 1:1 and there was a strong interaction between the host and the guest. The host-guest complex constant was calculated to be 2.458×10⁴ L/mol by the non-linear least squares curve fitting method. Analytical test results showed that the inclusion complex was successfully prepared. The water solubility of MAA increased from 0.3463 to 6.123 mg/mL after the formation of the inclusion complex between MAA and PP6A, which effectively improved the water solubility of MAA. Semi-empirical molecular orbital method and molecular docking calculations indicated that there was no hydrogen bond formed between the host and the guest. MAA could enter the cavity of PP6A and formed a conformationally stable inclusion complex. PP6A was a good host for MAA, and the optimal mode was consistent with the NMR results.
- Maackiain,
- Water-soluble phosphate salt pillar[6]arene,
- Inclusion behavior,
- Molecule docking,
- Molecule dynamics
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