Supramolecular Binding Behavior and Solubilization of Cationic Cyclodextrins towards Liquiritigenin
10.19756/j.issn.0253-3820.241156
- VernacularTitle:阳离子型环糊精对甘草素的超分子包合行为及增溶作用
- Author:
Ying-Hui DENG
1
;
Dong-Jing ZHANG
;
Hai-Kun WANG
;
Jia-Xing CHEN
;
Shuang SONG
;
Bo YANG
;
Xia-Li LIAO
Author Information
1. 昆明理工大学生命科学与技术学院,昆明 650500;曲靖医学高等专科学校药学院,曲靖 655000
- Keywords:
Liquiritigenin;
Cationic cyclodextrin;
Inclusion behavior;
Amino side chain;
Solubilization
- From:
Chinese Journal of Analytical Chemistry
2025;53(2):289-299,中插20-中插30
- CountryChina
- Language:Chinese
-
Abstract:
Liquiritigenin(LG)is a flavone of pharmacological importance,however,its application potential is severely limited due to its poor water solubility.LG could be disassociated slightly in water to form phenolate anion,therefore,better solubilization effect is expected by inclusion with cationic cyclodextrins(CCDs).In this work,four kinds of CCDs modified with amino groups at the primary face were synthesized,and their solid inclusion complexes with LG were successfully prepared by preparing their saturated solutions.The formation of the solid inclusion complexes was confirmed by scanning electron microscopy(SEM)and powder X-ray diffraction(PXRD),and their supramolecular binding behavior in solution was studied using multiple techniques.A 1∶1 inclusion stoichiometry of inclusion complexation was defined using Job plot by ultraviolet-visible(UV-vis)spectroscopy,and their binding stability constants(Ks)were determined as 2862.77,3494.70,6521.85 and 9599.48 L/mol using UV-vis spectroscopic titration,far more superior to that of nativeβ-CD(Ks=236.79 L/mol).This indicated that the amino side chains on CCDs could actively participate in the inclusion complexation through anion-cation interactions,significantly strengthening the host-guest binding between CCDs and LG.The inclusion modes were further elucidated based on proton and two-dimensional rotating-frame overhauser enhancement spectroscopy(2D-ROESY)nuclear magnetic resonance(NMR)experiments and molecular docking.Water solubility of LG was dramatically promoted up to 4.9 mg/mL,which was 70-fold higher than that of native LG.This study could draw inspiration for the binding and solubilization of phenols such as flavones by design of cationic macrocyclic molecules.
