藏红花素-磷脂复合物：分子对接、分子动力学模拟、制备、表征及抗氧化活性
Crocin-Phospholipid Complex: Molecular Docking, Molecular Dynamics Simulation, Preparation, Characterization, and Antioxidant Activity.
作者信息
Rezaee Yasaman, Rezaee Elham, Karami Leila, Torshabi Maryam, Haeri Azadeh
机构信息
Department of Pharmaceutics and Pharmaceutical Nanotechnology, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
出版信息
Iran J Pharm Res. 2024 Mar 24;23(1):e144041. doi: 10.5812/ijpr-144041. eCollection 2024 Jan-Dec.
BACKGROUND
Crocin is a water-soluble carotenoid compound present in saffron ( L.), known for its wide range of pharmacological activities, including cardioprotective, hepatoprotective, anti-tumorigenic, anti-atherosclerosis, and anti-inflammatory effects.
OBJECTIVES
The instability of crocin, its low miscibility with oils, and poor bioavailability pose challenges for its pharmaceutical applications. This study aimed to design and prepare a crocin-phospholipid complex (CPC) and assess its physicochemical properties.
METHODS
The study investigated the formation of the complex and its binding affinity through molecular docking. Molecular dynamics (MD) simulations were conducted to find the optimal molar ratio of crocin to phospholipid for the complex's preparation. The CPC was produced using the solvent evaporation method. Techniques such as X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FTIR), field-emission scanning electron microscopy (FE-SEM), nuclear magnetic resonance (NMR), and solubility studies were utilized to characterize and confirm the formation of CPC. Additionally, the in vitro antioxidant activity of crocin and CPC was evaluated.
RESULTS
Molecular dynamic simulations explored molar ratios of 1: 1, 1: 1.5, and 1: 2 for crocin to phospholipid. The ratio of 1: 2 was found to be the most stable, exhibiting the highest probability of hydrogen bond formation. Molecular docking, FTIR, and NMR studies indicated hydrogen bond interactions between crocin and phospholipid, confirming CPC's formation. XRD and FE-SEM analyses showed a decrease in crocin's crystallinity within the phospholipid complex. Furthermore, the solubility of crocin in n-octanol was enhanced post-complexation, indicating an increase in crocin's lipophilic nature.
CONCLUSIONS
Phospholipid complexation emerges as a promising technique for enhancing the physicochemical characteristics of crocin.
背景
藏红花素是一种存在于藏红花（Crocus sativus L.）中的水溶性类胡萝卜素化合物，因其具有广泛的药理活性而闻名，包括心脏保护、肝脏保护、抗肿瘤、抗动脉粥样硬化和抗炎作用。
目的
藏红花素的不稳定性、与油类的低混溶性以及较差的生物利用度对其药物应用构成挑战。本研究旨在设计并制备藏红花素-磷脂复合物（CPC），并评估其理化性质。
方法
该研究通过分子对接研究复合物的形成及其结合亲和力。进行分子动力学（MD）模拟以找到制备复合物时藏红花素与磷脂的最佳摩尔比。采用溶剂蒸发法制备CPC。利用X射线衍射（XRD）、傅里叶变换红外光谱（FTIR）、场发射扫描电子显微镜（FE-SEM）、核磁共振（NMR）和溶解度研究等技术对CPC的形成进行表征和确认。此外，还评估了藏红花素和CPC的体外抗氧化活性。
结果
分子动力学模拟探讨了藏红花素与磷脂的摩尔比为1:1、1:1.5和1:2的情况。发现1:2的比例最稳定，表现出形成氢键的最高概率。分子对接、FTIR和NMR研究表明藏红花素与磷脂之间存在氢键相互作用，证实了CPC的形成。XRD和FE-SEM分析表明，磷脂复合物中藏红花素的结晶度降低。此外，络合后藏红花素在正辛醇中的溶解度增加，表明藏红花素的亲脂性增强。
结论
磷脂络合是一种有前景的技术，可用于改善藏红花素的理化特性。
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