Evaluation on the inclusion behavior of β-cyclodextrins with lycorine and its hydrochloride

Xinyue Sun; Yuan Li; Haiyang Yu; Xiaoning Jin; Xiaofei Ma; Yue Cheng; Yuping Wei; Yong Wang

doi:10.1016/j.molliq.2023.121658

Evaluation on the inclusion behavior of β-cyclodextrins with lycorine and its hydrochloride

J Mol Liq. 2023 Jun 1:379:121658. doi: 10.1016/j.molliq.2023.121658. Epub 2023 Mar 18.

Authors

Xinyue Sun¹, Yuan Li¹, Haiyang Yu², Xiaoning Jin¹, Xiaofei Ma¹, Yue Cheng¹, Yuping Wei¹, Yong Wang¹

Affiliations

¹ Department of Chemistry, School of Science, Tianjin University, 300354, China.
² State Key Laboratory of Component-based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, China.

Abstract

Lycorine (Lyc) and its hydrochloride (Lyc∙HCl) as effective drugs can fight against many diseases including novel coronavirus (COVID-19) based on their antiviral and antitumor mechanism. Beta-cyclodextrin (β-CD) is considered a promising carrier in improving its efficacy while minimizing cytotoxicity due to the good spatial compatibility with Lyc. However, the detailed mechanism of inclusion interaction still remains to be further evaluated. In this paper, six inclusion complexes based on β-CDs, Lyc and Lyc∙HCl were processed through ultrasound in the mixed solvent of ethanol and water, and their inclusion behavior was characterized after lyophilization. It was found that the inclusion complexes based on sulfobutyl-beta-cyclodextrin (SBE-β-CD) and Lyc∙HCl had the best encapsulation effect among prepared inclusion complexes, which may be attributed to the electrostatic interaction between sulfonic group of SBE-β-CD and quaternary amino group of Lyc∙HCl. Moreover, the complexes based on SBE-β-CD displayed pH-sensitive drug release property, good solubilization, stability and blood compatibility, indicating their potential as suitable drug carriers for Lyc and Lyc∙HCl.

Keywords: Beta-cyclodextrins; Electrostatic interaction; Inclusion behavior; Lycorine; Lycorine hydrochloride.