Faculty of Life Science and Technology, Kunming University of Science and Technology, 650500 Kunming, China.
Faculty of Life Science and Technology, Kunming University of Science and Technology, 650500 Kunming, China; Jiangsu Xinchen Pharmaceutical Co., LTD, 222047 Lianyungang, China.
Mater Sci Eng C Mater Biol Appl. 2020 Jan;106:110161. doi: 10.1016/j.msec.2019.110161. Epub 2019 Sep 5.
Solid inclusion complexes between chrysin and four amino-appended β-cyclodextrins (ACDs) were prepared by suspension method and characterized in solid and solution states by kinds of analytical methods. The scanning electron microscopy (SEM) showed distinct micro-morphologies of them. Thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) analysis revealed their unique thermal properties, such as decomposition temperatures and endothermic points. Powder X-ray diffractometry (XRD) analysis disclosed their unique crystal patterns. Their nuclear magnetic resonance (NMR) analyses provided the variations of chemical shifts before and after the formation of inclusion complexes. Their binding stability constants (Ks) were 574, 842, 704, and 474 L·mol, respectively, as determined by spectral titration. A 1:1 inclusion mode with self-assembly of their amino side chains inside the ACD cavity was proposed based on Job plot and 2D-ROESY experiments. Water solubility of chrysin was promoted up to 4411.98 μg·mL after formation of inclusion complexes with ACDs, better than that of β-CD and its derivatives, i.e., HP- and SBE-β-CD. In vitro antioxidant activity of chrysin was also improved after inclusion complexation by the DPPH scavenging assay. Furthermore, in vitro cytotoxicity of solid inclusion complexes towards three human cancer cell lines, A549, HT-29 and HCT116 were enhanced significantly.
采用悬浮法制备了白杨素与四种氨基修饰的β-环糊精（ACDs）的固体包合物，并通过多种分析方法在固相与溶液状态下对其进行了表征。扫描电子显微镜（SEM）显示了它们明显的微观形态。热重分析（TGA）和差示扫描量热法（DSC）分析揭示了它们独特的热性能，如分解温度和吸热点。粉末 X 射线衍射（XRD）分析揭示了它们独特的晶体图案。它们的核磁共振（NMR）分析提供了形成包合物前后化学位移的变化。通过光谱滴定法确定了它们的结合稳定常数（Ks）分别为 574、842、704 和 474 L·mol。根据工作曲线和二维 ROESY 实验，提出了一种 1:1 的包合模式，其中它们的氨基侧链在 ACD 空腔内自组装。与 ACD 形成包合物后，白杨素的水溶性提高到 4411.98 μg·mL，优于β-CD 及其衍生物，即 HP-β-CD 和 SBE-β-CD。通过 DPPH 清除试验，包合后白杨素的体外抗氧化活性也得到了提高。此外，固体包合物对三种人癌细胞系 A549、HT-29 和 HCT116 的体外细胞毒性显著增强。
