In situ self-assembly of artesunate-β-cyclodextrin supramolecular nanomedicine as potential anti-cancer prodrug

IF 4 2区化学 Q2 CHEMISTRY, PHYSICAL Journal of Molecular Structure Pub Date : 2024-09-11 DOI:10.1016/j.molstruc.2024.139976

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Abstract

Supramolecular nanomedicines have drawn great interest in cancer therapy, but their potential immunotoxicities restrict application in clinical translation. Herein, we constructed a supramolecular nanomedicine CD-Artesunate (CD-ATS) in situ by supramolecular polymerization and orthogonal self-assembly. The nanostructure was meticulously characterized using 1D and 2D Nuclear Magnetic Resonance (NMR) spectroscopy, Mass spectrometry, Transmission Electron Microscopy (TEM), and particle size distribution analysis. β-cyclodextrin (β-CD) hosts are conjugated with artesunate (ATS) by click chemistry to improve the solubility and antitumor activity of ATS. Supramolecular nanomedicine was prepared through orthogonal self-assembly driven by host−guest complexation and hydrogen bonds. The results showed that the aqueous solubility of CD-ATS was 30 times better than that of free ATS. Furthermore, CD-ATS displayed a superior antitumor effect against HCT116 tumor cells compared to the first-line drug Taxol. This enhanced effect was attributed to the induction of excessive reactive oxygen species (ROS) generation, which subsequently triggered apoptosis.

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原位自组装青蒿琥酯-β-环糊精超分子纳米药物作为潜在的抗癌原药

超分子纳米药物在癌症治疗中备受关注，但其潜在的免疫毒性限制了其在临床上的应用。在此，我们利用超分子聚合和正交自组装技术，在原位构建了超分子纳米药物 CD-阿特逊酸酯（CD-ATS）。利用一维和二维核磁共振（NMR）光谱、质谱、透射电子显微镜（TEM）和粒度分布分析对该纳米结构进行了细致的表征。通过点击化学将β-环糊精（β-CD）宿主与青蒿琥酯（ATS）共轭，提高了青蒿琥酯的溶解度和抗肿瘤活性。在主客体复配和氢键的驱动下，通过正交自组装制备了超分子纳米药物。结果表明，CD-ATS的水溶性是游离ATS的30倍。此外，与一线药物 Taxol 相比，CD-ATS 对 HCT116 肿瘤细胞的抗肿瘤效果更佳。这种增强效果归因于诱导产生过多的活性氧（ROS），进而引发细胞凋亡。

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来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.