The mechanochemical and supercritical fluid synthesis of β-cyclodextrin-hesperidin inclusion complex: A comparison green chemistry versus lyophilization

IF 3.4 3区工程技术 Q2 CHEMISTRY, PHYSICAL Journal of Supercritical Fluids Pub Date : 2024-10-03 DOI:10.1016/j.supflu.2024.106422

Luis José López-Méndez , Rubria Marlen Martínez-Cásares , Alberto López-Luna , Héctor Luna , Patricia Guadarrama , Rosa Estrada-Reyes , Raúl G. Enríquez , Julia Cassani

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Abstract

Hesperidin is a rutinoside of flavanone type with relevant therapeutic properties but poor water solubility which limits its therapeutic applicability. However, cyclodextrins (CDs) have been successfully used as drug carriers to enhance the solubility of several drugs, to improve their bioavailability, and therapeutic efficacy. We report herein the formation of inclusion complexes of β-cyclodextrin and hesperidin through the green approaches mechanochemistry and supercritical fluid and compare these results versus the classical lyophilization method. The resulting stoichiometries and the specific interactions of the complexes were analyzed by NMR, UV, and mass spectrometry. The β-cyclodextrin and hesperidin inclusion complex (IC) successfully obtained through green methodologies demonstrated superior levels of flavonoid content. In terms of solubility, the mechanochemistry inclusion complex showed the best improvement in solubility. We demonstrate herein that the use of green methodologies such as supercritical fluids and mechanochemistry are useful alternatives to the conventional method of lyophilization, to improve the solubility of β-cyclodextrin IC.

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β-环糊精-橙皮甙包合物的机械化学和超临界流体合成：绿色化学与冻干法的比较

橙皮甙是一种黄酮类芸香甙，具有相关的治疗特性，但水溶性较差，限制了其治疗适用性。然而，环糊精（CD）已被成功用作药物载体，以提高多种药物的溶解度、生物利用度和治疗效果。我们在此报告了通过机械化学和超临界流体的绿色方法形成的β-环糊精和橙皮甙的包合物，并将这些结果与经典的冻干方法进行了比较。通过核磁共振、紫外和质谱分析了所得复合物的化学计量和特定相互作用。通过绿色方法成功获得的β-环糊精和橙皮甙包合物（IC）显示出卓越的类黄酮含量。在溶解度方面，机械化学包合物的溶解度改善最好。我们在此证明，使用超临界流体和机械化学等绿色方法可有效替代传统的冻干法，提高β-环糊精包合物的溶解度。

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来源期刊

Journal of Supercritical Fluids 工程技术-工程：化工

CiteScore

7.60

自引率

10.30%

发文量

236

审稿时长

56 days

期刊介绍： The Journal of Supercritical Fluids is an international journal devoted to the fundamental and applied aspects of supercritical fluids and processes. Its aim is to provide a focused platform for academic and industrial researchers to report their findings and to have ready access to the advances in this rapidly growing field. Its coverage is multidisciplinary and includes both basic and applied topics. Thermodynamics and phase equilibria, reaction kinetics and rate processes, thermal and transport properties, and all topics related to processing such as separations (extraction, fractionation, purification, chromatography) nucleation and impregnation are within the scope. Accounts of specific engineering applications such as those encountered in food, fuel, natural products, minerals, pharmaceuticals and polymer industries are included. Topics related to high pressure equipment design, analytical techniques, sensors, and process control methodologies are also within the scope of the journal.