Effect of Protocatechuic Acid Ethyl Ester on Biomembrane Models: Multilamellar Vesicles and Monolayers

Torrisi, Cristina; Malfa, Giuseppe Antonio; Acquaviva, Rosaria; Castelli, Francesco; Sarpietro, Maria Grazia

doi:10.3390/membranes12030283

Cited by 8 publications

(5 citation statements)

References 32 publications

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“…It can be suggested that the acyl chains of the tristearoyl cytarabine could partly protrude from the monolayer, and the protruding part would not interact with it. In accord with to results shown, the biomembrane models can serve as a simplified cell membrane [ 36 , 37 ]. In this work, two lipophilic derivatives of cytarabine were obtained by conjugation of cytarabine with myristic acid and stearic acid, respectively.…”

Section: Discussionsupporting

confidence: 55%

“…In this study, the thermodynamic properties of the phospholipid monolayer change considerably with the incorporation of lipophilic derivatives of cytarabine with fatty acids. Langmuir monolayer data suggested a significant molecular-level interaction between acyl derivatives of cytarabine and DMPC; therefore, they are absorbed and dissolved through the biomembrane models [ 36 , 37 ]. The results indicate that the lipophilic derivatives of the nucleoside are able to penetrate into condensed phospholipid monolayers and form stable Langmuir monolayers due to the strong interaction of London and Dipole–Dipole forces among the polar heads and lipophilic chains of amphiphilic prodrugs and DMPC molecules, respectively.…”

Section: Discussionmentioning

confidence: 99%

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Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface

et al. 2022

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Cell membrane models are useful for obtaining molecular-level information on the interaction of biologically active molecules whose activity is believed to depend also on their effects on the membrane. Cytarabine was conjugated with fatty acids to improve the drug lipophilicity and the interaction with the biomembrane model. Cytarabine was conjugated with fatty acids of different lengths to form the trimyristoyl cytarabine and the tristearoyl cytarabine derivatives. Their interaction with biomembrane models constituted by dimyristoylphosphatidylcholine (DMPC) monolayers was studied by employing the Langmuir–Blodgett technique. DMPC/cytarabine, DMPC/trimyristoyl cytarabine and DMPC/tristearoyl cytarabine mixed monolayers at increasing molar fractions of the compound were prepared and placed on the subphase. The mean molecular area/surface pressure isotherms were recorded at 37 °C. Between the molecules of DMPC and those of cytarabine or prodrugs, repulsive forces act. However, these forces are very weak between DMPC and cytarabine and stronger between DMPC and the cytarabine derivatives, thus avoiding the expulsion of the compounds at higher surface pressure and modifying the stability of the mixed monolayer. The fatty acid moieties could then modulate the affinity of cytarabine for biomembranes.

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Section: Discussionsupporting

confidence: 55%

Section: Discussionmentioning

confidence: 99%

Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface

et al. 2022

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“…From the DSC thermograms, we obtained melting transition temperature (Tm) and cooperativity (κ) as a readout of both lipid-lipid interaction and membrane organization (Fig. 5e ) 54 , 55 . LA displayed the lowest melting temperature (i.e., less temperature required to transition from the gel to the liquid phase) compared to DPPC alone or liposomes containing SA, OA, γLA, DγLA, AA, or DTA (Fig.…”

Section: Resultsmentioning

confidence: 99%

Linoleic acid improves PIEZO2 dysfunction in a mouse model of Angelman Syndrome

et al. 2023

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Angelman syndrome (AS) is a neurogenetic disorder characterized by intellectual disability and atypical behaviors. AS results from loss of expression of the E3 ubiquitin-protein ligase UBE3A from the maternal allele in neurons. Individuals with AS display impaired coordination, poor balance, and gait ataxia. PIEZO2 is a mechanosensitive ion channel essential for coordination and balance. Here, we report that PIEZO2 activity is reduced in Ube3a deficient male and female mouse sensory neurons, a human Merkel cell carcinoma cell line and female human iPSC-derived sensory neurons with UBE3A knock-down, and de-identified stem cell-derived neurons from individuals with AS. We find that loss of UBE3A decreases actin filaments and reduces PIEZO2 expression and function. A linoleic acid (LA)-enriched diet increases PIEZO2 activity, mechano-excitability, and improves gait in male AS mice. Finally, LA supplementation increases PIEZO2 function in stem cell-derived neurons from individuals with AS. We propose a mechanism whereby loss of UBE3A expression reduces PIEZO2 function and identified a fatty acid that enhances channel activity and ameliorates AS-associated mechano-sensory deficits.

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“…The process was repeated three times to check the reproducibility of results. Unloaded MLV were also analyzed to be used as reference [25].…”

Section: Unloaded and Bxl-loaded-mlv Analysismentioning

confidence: 99%

Characterization and Interaction with Biomembrane Model of Benzo[k,l]xanthene Lignan Loaded Solid Lipid Nanoparticles

et al. 2022

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Benzo[k,l]xanthene lignans are a group of rare natural products belonging to the class of polyphenols with promising biological activities and are studied as potential chemotherapeutic agents. The lipophilic character of a xanthene core makes these molecules difficult to be used in an aqueous medium, limiting their employment in studies for pharmaceutical applications. To overcome this problem, a drug-delivery system which is able to improve the stability and bioavailability of the compound can be used. In this study, a bioactive benzoxanthene lignan (BXL) has been included in SLN. Unloaded and BXL-loaded SLN have been prepared using the Phase Inversion Temperature method and characterized in terms of size, zeta potential, entrapment efficiency and stability. Differential scanning calorimetry was used to evaluate the thermotropic behavior and ability of SLN to act as carriers for BXL. A biomembrane model, represented by multilamellar vesicles, was used to simulate the interaction of the SLN with the cellular membrane. Unloaded and loaded SLN were incubated with the MLV, and their interactions were evaluated through variations in their calorimetric curves. The results obtained suggest that SLN could be used as a delivery system for BXL.

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Effect of Protocatechuic Acid Ethyl Ester on Biomembrane Models: Multilamellar Vesicles and Monolayers

Cited by 8 publications

References 32 publications

Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface

Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface

Linoleic acid improves PIEZO2 dysfunction in a mouse model of Angelman Syndrome

Characterization and Interaction with Biomembrane Model of Benzo[k,l]xanthene Lignan Loaded Solid Lipid Nanoparticles

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