A calorimetric evaluation of the interaction of amphiphilic prodrugs of idebenone with a biomembrane model

Does hydrophobicity always enhance antioxidant drugs? A cut-off effect of the chain length of functionalized chlorogenate esters on ROS-overexpressing fibroblasts

“…In contrast, it is well documented that hydrophobicity can strongly favour the cell membrane uptake or penetration of amphiphilic molecules by giving them the so-called 'membrane-like character'. [19,20] In this way, a passive or assisted membrane transfer enabling an intracellular location of phenolics (presumably close to the oxidizing species) could strongly favour an antioxidant action and therefore could explain the strong activity of dodecyl and hexadecyl chlorogenates (Figure 2e and 2f). Besides, Serrano et al [7] reported that the dodecyl ester of gallic acid presents a better membrane-crossing action than its propyl homologue.…”

Interaction of naproxen amphiphilic derivatives with biomembrane models evaluated by differential scanning calorimetry and Langmuir–Blodgett studies

“…MLV exhibit, under heating, a characteristic transition from the gel (L b ) phase to the liquid crystal (L a ) phase [13][14][15][16] that can be revealed by DSC by measuring the associated thermodynamic parameters (transition temperature, T m , and enthalpy changes, DH). Amphiphilic compounds, interacting with the phospholipid bilayers, may cause modification of the lipid chain packing, resulting in a variation of the transition thermodynamic parameters [11,[16][17][18][19][20][21][22][23][24]. This behavior, which can be analyzed by the Van't Hoff model of the freezing point depression of solutions, has been verified for several classes of chemical compounds, such as anesthetics [24], and applied on theoretical basis by some researchers [24][25][26]; the deviations from the model due to the complex structure as well as to the size of the compounds have been also taken into account [15,27].…”

Nucleic acid-lipid membrane interactions studied by DSC

“…[10] A large amount of work has already been published presenting results from extensive studies of interactions of lipid membranes with biomolecules, primarily explored by DSC, where the molecular order of lipids and the thermally induced phase transitions were probed. [11–13] Even though DSC proved to be a powerful and easy-to-operate technique, it became clear that for the correct interpretation and the deeper understanding of the calorimetric data, that is, heat capacity vs. temperature, the correlation of DSC with structural information from a variety of combined techniques was necessary. [14–19]…”