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

Micieli, Dorotea; Giuffrida, Maria Chiara; Pignatello, Rosario; Castelli, Francesco; Sarpietro, Maria Grazia

doi:10.1016/j.jcis.2011.04.092

Cited by 11 publications

(6 citation statements)

References 35 publications

(34 reference statements)

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“…It is worth summarizing at this point how the results extracted from our MD simulations match the available experimental evidence: − ,, NAP – finds an equilibrium position at the polar/nonpolar interface of the lipid membrane, as was established by Förster resonance energy transfer (FRET). A lack of heat transfer during isothermal titration calorimetry suggests that entropy plays a major role in the insertion process, and the precedent dissection of the interplay between the entropy and enthalpy terms provides solid evidence to conclude that entropy is indeed the major thermodynamic factor dominating the entire insertion path.…”

Section: Resultssupporting

confidence: 69%

Thermodynamics and Intermolecular Interactions during the Insertion of Anionic Naproxen into Model Cell Membranes

et al. 2021

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The insertion process of Naproxen into model dimyristoylphosphatidylcholine (DMPC) membranes is studied by resorting to state-ofthe-art classical and quantum mechanical atomistic computational approaches. Molecular dynamics simulations indicate that anionic Naproxen finds an equilibrium position right at the polar/nonpolar interphase when the process takes place in aqueous environments. With respect to the reference aqueous phase, the insertion process faces a small energy barrier of ≈5 kJ mol −1 and yields a net stabilization of also ≈5 kJ mol −1 . Entropy changes along the insertion path, mainly due to a growing number of realizable microstates because of structural reorganization, are the main factors driving the insertion. An attractive fluxional wall of noncovalent interactions is characterized by allquantum descriptors of chemical bonding (natural bond orbitals, quantum theory of atoms in molecules, noncovalent interaction, density differences, and natural charges). This attractive wall originates in the accumulation of tiny transfers of electron densities to the interstitial region between the fragments from a multitude of individual intermolecular contacts stabilizing the tertiary drug/water/membrane system.

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Section: Resultssupporting

confidence: 69%

Thermodynamics and Intermolecular Interactions during the Insertion of Anionic Naproxen into Model Cell Membranes

et al. 2021

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“…This could indicate that the compounds leave the interface and transfer to the aqueous subphase. 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 ).…”

Section: ■ Results and Discussionsupporting

confidence: 87%

Effect of Resveratrol-Related Stilbenoids on Biomembrane Models

et al. 2013

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The interactions of the two resveratrol analogues 2-hydroxy-3,5,3',5'-tetramethoxystilbene (4) and 2-hydroxy-3,5,3',4'-tetramethoxystilbene (5) with model biomembranes were studied. The aim of this investigation was to highlight possible differences in the interactions with such biomembranes related to the minimal structural differences between these isomeric stilbenoids. In particular, different experiments on stilbenoid/biomembrane model systems using both differential scanning calorimetry (DSC) and Langmuir-Blodgett techniques were carried out to evaluate stilbenoid/multilamellar vesicle and stilbenoid/phospholipid monolayer interactions, respectively. Dimyristoylphosphatidylcholine was used as constituent of the biomembrane models and permitted the experiments to be carried out at 37 °C, close to body temperature. Kinetic studies were also run by DSC to evaluate the uptake of the resveratrol derivatives by the biomembrane model in an aqueous medium and when transported by a lipophilic carrier. The results indicated that both of the resveratrol analogues influenced the behavior of multilamellar vesicles and monolayers, biomembrane models, with 4 producing a larger effect than 5. These results are useful for better understanding the mechanism of action of these compounds. Moreover, the kinetic results could be of importance for future design of lipophilic delivery systems for these stilbenoids.

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“…Typical examples include: antimicrobials [117,, anti-tumorals [116,, antiinflammatory [77,[214][215][216][217], anesthesics [218][219][220][221][222][223][224][225][226][227], anti-psychotics [228][229][230][231][232][233][234][235][236][237], cardiac [238][239][240][241][242][243][244][245] and antihistaminic [246] drugs. To address this issue, Langmuir monolayers have been used involving AmB alone as well as mixed with membrane sterols.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…This effect, confirmed with PM-IRRAS [215], was stronger and concentration- anti-inflammatory drugs have been applied to treat this ailment. Naproxen and its amphiphilic and lipophilic conjugates with long-chained aminoacid were investigated in DMPC monolayers [217]. Analogously to the effects from ibuprofen, these drugs caused a fluidizing effect and a decrease in monolayer compressibility.…”

Section: Anti-inflammatory Drugsmentioning

confidence: 99%

Interactions of bioactive molecules & nanomaterials with Langmuir monolayers as cell membrane models

et al. 2015

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

Cited by 11 publications

References 35 publications

Thermodynamics and Intermolecular Interactions during the Insertion of Anionic Naproxen into Model Cell Membranes

Thermodynamics and Intermolecular Interactions during the Insertion of Anionic Naproxen into Model Cell Membranes

Effect of Resveratrol-Related Stilbenoids on Biomembrane Models

Interactions of bioactive molecules & nanomaterials with Langmuir monolayers as cell membrane models

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