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芦丁-环糊精包合物的制备、表征及分子动力学模拟。

Preparation, Characterization and Molecular Dynamics Simulation of Rutin-Cyclodextrin Inclusion Complexes.

机构信息

School of Materials and Chemical Engineering, Zhongyuan University of Technology, Zhengzhou 450007, China.

出版信息

Molecules. 2023 Jan 18;28(3):955. doi: 10.3390/molecules28030955.

DOI:10.3390/molecules28030955
PMID:36770635
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9919933/
Abstract

Rutin is a natural flavonoid that carries out a variety of biological activities, but its application in medicine and food is limited by its water solubility. One of the classical methods used to enhance drug solubility is encapsulation with cyclodextrins. In this paper, the encapsulation of different cyclodextrins with rutin was investigated using a combination of experimental and simulation methods. Three inclusions of rutin/beta-cyclodextrin (β-CD), rutin/2-hydroxypropyl beta-cyclodextrin (HP-β-CD) and rutin/2,6-dimethyl beta-cyclodextrin (DM-β-CD) were prepared by the freeze-drying method, and the inclusions were analyzed using Fourier infrared spectroscopy (FTIR), X-ray diffraction analysis (XRD), differential scanning calorimetry (DSC) and ultraviolet-visible spectroscopy (UV) to characterize and demonstrate the formation of the inclusion complexes. Phase solubility studies showed that rutin formed a 1:1 stoichiometric inclusion complex and significantly increased its solubility. β-CD, HP-β-CD, DM-β-CD, rutin and the three inclusion complexes were modeled by using MS2018 and AutoDock 4.0, and molecular dynamics simulations were performed to calculate the solubility parameters, binding energies, mean square displacement (MSD), hydrogen bonding and radial distribution functions (RDF) after the equilibration of the systems. The results of simulation and experiment showed that rutin/DM-β-CD had the best encapsulation effect among the three cyclodextrin inclusion complexes.

摘要

芦丁是一种天然类黄酮，具有多种生物活性，但由于其水溶性有限，其在医学和食品中的应用受到限制。提高药物溶解度的经典方法之一是用环糊精包合。本文采用实验和模拟相结合的方法，研究了不同环糊精对芦丁的包合作用。采用冷冻干燥法制备了芦丁/β-环糊精（β-CD）、芦丁/2-羟丙基-β-环糊精（HP-β-CD）和芦丁/2,6-二甲基-β-环糊精（DM-β-CD）三种包合物，并采用傅里叶变换红外光谱（FTIR）、X 射线衍射分析（XRD）、差示扫描量热法（DSC）和紫外可见光谱（UV）对包合物进行分析，以表征和证明包合物的形成。相溶解度研究表明，芦丁形成了 1:1 的化学计量包合物，显著提高了其溶解度。采用 MS2018 和 AutoDock 4.0 对 β-CD、HP-β-CD、DM-β-CD、芦丁和三种包合物进行建模，并进行分子动力学模拟，计算系统达到平衡后的溶解度参数、结合能、均方根位移（MSD）、氢键和径向分布函数（RDF）。模拟和实验结果表明，在三种环糊精包合物中，芦丁/ DM-β-CD 的包合效果最好。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/595e/9919933/60a8a9645267/molecules-28-00955-g013.jpg
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