Dipartimento di Scienze Chimiche, Università degli Studi di Catania, Viale Andrea Doria 6, I-95125 Catania, Italy.
Int J Pharm. 2010 Mar 30;388(1-2):144-50. doi: 10.1016/j.ijpharm.2009.12.048. Epub 2010 Jan 4.
E-3,5,4'-trimethoxystilbene (TMS) is a naturally occurring analog of resveratrol. The anti-neoplastic, antiallergic and anti-angiogenic activities of TMS have been recently reported. From the viewpoint of metabolism, TMS may be more favourable than resveratrol because all of its hydroxyl groups, which are subjected to extensive glucuronide or sulphate conjugation in the metabolic pathways of resveratrol, are protected by methylation. Moreover, methylation increases lipophilicity and may enhance cell membrane permeability, but it decreases its solubility in aqueous media. A way to increase TMS solubility can be represented by complexation with beta-cyclodextrins. In the present paper, the differential scanning calorimetry technique has been used to study the interaction of TMS with a biomembrane model constituted by dimyristoylphosphatidylcholine multilamellar vesicles. Furthermore, kinetic experiments have been carried out to follow the uptake of TMS by biomembranes in the presence of beta-cyclodextrins to gain information on the effect of beta-cyclodextrins on the uptake process. Our results indicate that opportune concentrations of beta-cyclodextrins greatly improve the uptake of TMS by biomembrane models.
E-3,5,4'-三甲氧基二苯乙烯（TMS）是白藜芦醇的一种天然类似物。最近报道了 TMS 的抗肿瘤、抗过敏和抗血管生成活性。从代谢的角度来看，TMS 可能比白藜芦醇更有利，因为其所有的羟基都被甲基化保护，而白藜芦醇的代谢途径中这些羟基会受到广泛的葡萄糖醛酸或硫酸盐结合。此外，甲基化增加了亲脂性并可能增强细胞膜通透性，但降低了其在水介质中的溶解度。增加 TMS 溶解度的一种方法可以是与β-环糊精形成复合物。在本文中，差示扫描量热法已被用于研究 TMS 与由二肉豆蔻酰磷脂酰胆碱多层囊泡组成的生物膜模型的相互作用。此外，还进行了动力学实验来跟踪 TMS 在β-环糊精存在下被生物膜摄取，以获取关于β-环糊精对摄取过程影响的信息。我们的结果表明，适当浓度的β-环糊精可大大提高生物膜模型对 TMS 的摄取。
