Interaction of resveratrol analogues with biomembrane models: a calorimetric study on structural variations effects

Abstract

Differential Scanning Calorimetry was used to study the interaction of new resveratrol derivatives using dimyristoylphosphatidylcholine (DMPC) multilamellar vesicles (MLV) as biomembrane models. MLV prepared in the presence of increasing molar fractions of the following compounds: (A) 3,5,3’,5’- tetramethoxystilbene, (B) 3,5,3’,4’-tetramethoxystilbene, (C) 3,4,5,4’-tetramethoxystilbene, (D) 3,4,5,3’,5’- pentamethoxystilbene and (E) 3,4,2’,4’,5’-pentamethoxystilbene were analyzed to study the effects exerted by the number and position of the substituents on the variations of thermotropic properties of the biomembrane model. The results showed that the number and the position of the substituent strongly affected the interaction between the compounds and the MLV based on DMPC. Kinetic experiments demonstrated that, the absorption of compounds A to E is limited in an aqueous medium. The presence of a lipophilic medium improves the absorption of the compounds by the biomembrane model.