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Abstract
Isoliquiritigenin (ILTG) possesses many pharmacological properties. However, its poor solubility and stability in water hinders its wide applications. The solubility of bioactive compounds can often be enhanced through preparation and delivery of various cyclodextrin (CD) inclusion complexes. The 6-O-α-d-maltosyl-β-CD (G2-β-CD), as one of the newest developments of CDs, has high aqueous solubility and low toxicity, especially stable inclusion characteristics with bioactive compounds. In this work, we for the first time construct and characterize the supermolecular structure of ILTG/G2-β-CD by scanning electron microscopy (SEM), ultraviolet-visible spectroscopy (UV), Fourier transform infrared spectroscopy (FT-IR), and X-ray diffractometry (XRD). The solubility of ILTG in water at 25 °C rises from 0.003 to 0.717 mg/mL by the encapsulation with G2-β-CD. Our experimental observations on the presence of the ILTG/G2-β-CD inclusion complex are further supported by the ONIOM(our Own N-layer Integrated Orbital molecular Mechanics)-based QM/MM (Quantum Mechanics/Molecular Mechanics) calculations, typically substantiating these supermolecular characteristics, such as detailed structural assignments, preferred binding orientations, selectivity, solvent effects, interaction energies and forces of the ILTG/G2-β-CD inclusion complex. Our results have elucidated how ILTG interacts with G2-β-CD, demonstrating the primary host-guest interactions between ILTG and G2-β-CD, characterized by hydrogen bonds, hydrophobic interactions, electrostatic forces, and conformational effects, are favored for the formation of the ILTG/G2-β-CD inclusion.
Highlights
Isoliquiritigenin (ILTG, Figure 1A), which possesses a basic structure of two benzene rings linked through an α, β-unsaturated carbonyl group, is a chalcone compound that is found in various medicinal plants such as Glycyrrhiza uralensis, Allium ascalonicum, Sinofranchetia chinensis, Dalbergia odorifera, and Glycine max L. [1,2]
The solubility of ILTG in water is enhanced by forming the inclusion complex with G2-β-CD
We characterize the supermolecular structure of the ILTG/G2-β-CD inclusion complex as experimentally evidenced by scanning electron microscopy (SEM), ultraviolet-visible spectroscopy (UV), Fourier transform infrared spectroscopy (FT-IR), and X-ray diffractometry (XRD)
Summary
Isoliquiritigenin (ILTG, Figure 1A), which possesses a basic structure of two benzene rings linked through an α, β-unsaturated carbonyl group, is a chalcone compound that is found in various medicinal plants such as Glycyrrhiza uralensis (licorice), Allium ascalonicum, Sinofranchetia chinensis, Dalbergia odorifera, and Glycine max L. [1,2]. The accuracy of semiempirical calculations (such as AM1 and PM3) is relative low, and the DFT methods are prohibitively expensive to carry out studies on such large systems, and for MD methods [9,28], it is difficult to construct the force fields for CD variations and guest molecules. To overcome these drawbacks, a hybrid ONIOM (our Own N-layer Integrated Orbital molecular Mechanics) method [29]. Our experimental and theoretical results have mutually supported to clarify how ILTG interacts with G2-β-CD
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