Evaluation of the Interaction of Coumarins with Biomembrane Models Studied by Differential Scanning Calorimetry and Langmuir−Blodgett Techniques

Abstract

Three coumarins, scopoletin (1), esculetin (2), and esculin (3), were investigated by differential scanning calorimetry and Langmuir-Blodgett techniques to gain information about the interaction of these compounds with cellular membranes. Phospholipids assembled as multilamellar vesicles or monolayers (at the air-water interface) were used as biomembrane models. Differential scanning calorimetry was employed to study the interaction of these coumarins with multilamellar vesicles and to evaluate their absorption by multilamellar vesicles. These experiments indicated that 1-3 interact in this manner to different extents. The Langmuir-Blodgett technique was used to study the effect of these coumarins on the organization of phospholipids assembled as a monolayer. The data obtained were in agreement with those obtained in the calorimetric experiments.

Effect of Resveratrol-Related Stilbenoids on Biomembrane Models

“…This could indicate that the compounds leave the interface and transfer to the aqueous subphase. This behavior is similar to that observed with naproxen and some coumarins . At 10 °C, the isotherm of DMPC, going from 120 to about 42 Å 2 , is characterized by a gaseous state (120–100 Å 2 ), a liquid expanded state (100–65 Å 2 ), a liquid expanded–liquid compressed transition (65–50 Å 2 ), and a liquid compressed state (50–42 Å 2 ) .…”

“…This behavior is similar to that observed with naproxen 43 and some coumarins. 44 At 10 °C, the isotherm of DMPC, going from 120 to about 42 Å 2 , is characterized by a gaseous state (120−100 Å 2 ), a liquid expanded state (100−65 Å 2 ), a liquid expanded−liquid compressed transition (65−50 Å 2 ), and a liquid compressed state (50−42 Å 2 ). 45 Compound 4 did not produce significant variation of the isotherm up to a 0.12 molar fraction; from 0.25 molar fraction, the gradual shift of the isotherm toward lower values of molecular area was observed, and this occurred always with a decrease of the liquid expanded−liquid compressed transition.…”

Interaction of a Phospholipid and a Coagulating Protein: Potential Candidate for Bioelectronic Applications

“…The Langmuir–Blodgett (LB) method is one of the best techniques to mimic and study an artificial biomembrane. , This technique allows one to investigate the thermodynamic behavior and the biophysical and biochemical processes within the membrane, , interaction between various membrane components, and other suitable molecules like drugs, antibiotics, proteins, lipids, polymers, surfactants, and various other biomacromolecules. , The main advantage of the LB method is that one can have molecular level control during membrane formation. − Using the LB method, one can prepare bilayer assemblies with various lipid compositions and structural arrangements . This key feature of the LB technique allows preparation of asymmetric lipid assemblies .…”

Esculetin: A review of its pharmacology and pharmacokinetics

“…The demand for the in vivo analysis of esculetin as well as the systematic publication of research on its pharmacokinetics is growing, although information on this is currently limited. Natural coumarins and their derivatives were previously confirmed to exist in the form of free or combined glycosides, including esculin as the glucoside of esculetin (Sarpietro, Giuffrida, Ottimo, Micieli, & Castelli, 2011) cating that the absorption of the esculin in beagle dogs was less than that of the esculetin, as well as that the absorption speed of the esculin was slower than that of the esculetin. Besides, the elimination half-life (T 1/2 ) was identified to be 3.43 ± 0.47 hr for esculin and 4.25 ± 0.18 hr for esculetin, implying that esculetin is eliminated in a slower manner than esculin (Wang et al, 2018).…”