The Modulating Effect of p-Coumaric Acid on The Surface Charge Density of Human Glioblastoma Cell Membranes

Kruszewski, Marcin Andrzej; Kotyńska, Joanna; Kusaczuk, Magdalena; Gál, Miroslav; Naumowicz, Monika

doi:10.3390/ijms20215286

Cited by 9 publications

(11 citation statements)

References 46 publications

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“…LN-229 cells treated with either CA or FA showed an increase in positive charge at low pH and a decrease in negative charge at high pH in comparison to untreated cells. These results seem to be in agreement with other reports demonstrating similar tendency for various cancer cell membranes treated with chemotherapeutic agents [ 18 , 57 , 58 ]. It has already been well documented that polyphenols exhibit affinity for the lipid bilayer by binding to the lipid head groups near the bilayer surface (adsorption) and penetration into the bilayer interface (absorption).…”

Section: Discussionsupporting

confidence: 93%

“…One of the techniques that might be used to estimate zeta potential is the electrophoretic light scattering (ELS) technique based on dynamic light scattering (DLS), in which the shift in the frequency or in the oscillation phase of the laser beam depends on the mobility of particles/cells in an alternating electric field [ 14 ]. In this respect, in our previous works, we have already applied the ELS technique to study human glioblastoma cells treated with either silica nanoparticles [ 14 , 15 ] or phenolic compounds such as quercitin [ 16 ] and p-coumaric acid [ 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

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Monitoring of the Surface Charge Density Changes of Human Glioblastoma Cell Membranes upon Cinnamic and Ferulic Acids Treatment

Naumowicz

Kusaczuk

Zając

et al. 2020

IJMS

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Cinnamic acid (CA) and ferulic acid (FA) are naturally occurring phenolic acids claimed to exert beneficial effects against disorders related to oxidative stress, including cancer. One such malignancy that still remains a therapeutic challenge mainly due to its heterogeneity and inaccessibility to therapeutic agents is Glioblastoma multiforme (GBM). Here, the influence of CA and FA on the surface charge density of human GBM cell line LN-229 was studied using the electrophoretic light scattering technique. Also, the cytotoxicity of both phenolic acids was determined by metabolic activity-assessing tetrazolium test (MTT) analysis after exposure to CA and FA for 24 h and 48 h. Results showed that both compounds reduced cell viability of LN-229 cells, with more pronounced effect evoked by CA as reflected in IC50 values. Further analyses demonstrated that, after treatment with both phenolic acids, the negative charge of membranes decreased at high pH values and the positive charge of the membranes increased at low pH values compared to the data obtained for untreated cells. Afterward, a four-equilibrium model was applied to estimate the total surface concentrations of both acidic and basic functional groups and their association constants with solution ions in order to calculate theoretical values of membrane surface charge densities. Then, the theoretical data were compared to the experimental data in order to verify the mathematical model. As such, our results indicate that application of electrochemical methods to determine specific drug–membrane interactions might be crucial for predicting their pharmacological activity and bioavailability.

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Section: Discussionsupporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Monitoring of the Surface Charge Density Changes of Human Glioblastoma Cell Membranes upon Cinnamic and Ferulic Acids Treatment

Naumowicz

Kusaczuk

Zając

et al. 2020

IJMS

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“…The location and permeability of polyphenols through membranes depends on the pH and charge. For example, using model lipid membranes, it was shown that at a lower pH, p -coumaric acid has a lower deprotonation state and penetrates deeper into the cell, so this is a feature conditioning its biological efficiency [ 218 ].…”

Section: Structure Elements and Biological Activitymentioning

confidence: 99%

Biologically Active Compounds of Plants: Structure-Related Antioxidant, Microbiological and Cytotoxic Activity of Selected Carboxylic Acids

et al. 2020

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Natural carboxylic acids are plant-derived compounds that are known to possess biological activity. The aim of this review was to compare the effect of structural differences of the selected carboxylic acids (benzoic acid (BA), cinnamic acid (CinA), p-coumaric acid (p-CA), caffeic acid (CFA), rosmarinic acid (RA), and chicoric acid (ChA)) on the antioxidant, antimicrobial, and cytotoxic activity. The studied compounds were arranged in a logic sequence of increasing number of hydroxyl groups and conjugated bonds in order to investigate the correlations between the structure and bioactivity. A review of the literature revealed that RA exhibited the highest antioxidant activity and this property decreased in the following order: RA > CFA ~ ChA > p-CA > CinA > BA. In the case of antimicrobial properties, structure-activity relationships were not easy to observe as they depended on the microbial strain and the experimental conditions. The highest antimicrobial activity was found for CFA and CinA, while the lowest for RA. Taking into account anti-cancer properties of studied NCA, it seems that the presence of hydroxyl groups had an influence on intermolecular interactions and the cytotoxic potential of the molecules, whereas the carboxyl group participated in the chelation of endogenous transition metal ions.

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“…In line with previous reports, many of these compounds may act as chemopreventive or even chemotherapeutic agents [ 5 , 7 , 8 , 9 ]. Specifically to malignant cells, cinnamic acid (CinA) and its hydroxy derivatives have been shown to exhibit both antioxidant a antineoplastic activity, with their cytostatic effect being largely related to their structural characteristics [ 10 , 11 , 12 , 13 ]. However, the mode of action of CinA and its derivatives is still incompletely determined, but may involve scavenging of reactive oxygen species, modulation of gene expression, activation of xenobiotics metabolism-related enzymes, and regulation of signal transduction pathways essential for tumor cell growth and progression [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Electrophoretic Light Scattering and Electrochemical Impedance Spectroscopy Studies of Lipid Bilayers Modified by Cinnamic Acid and Its Hydroxyl Derivatives

et al. 2020

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Pharmacological efficiency of active compounds is largely determined by their membrane permeability. Thus, identification of drug-membrane interactions seems to be a crucial element determining drug-like properties of chemical agents. Yet, knowledge of this issue is still lacking. Since chemoprevention based on natural compounds such as cinnamic acid (CinA), p-coumaric acid (p-CoA) and ferulic (FA) is becoming a strong trend in modern oncopharmacology, determination of physicochemical properties of these anticancer compounds is highly important. Here, electrophoretic light scattering and impedance spectroscopy were applied to study the effects of these phenolic acids on electrical properties of bilayers formed from 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-diacyl-sn-glycero-3-phospho-l-serine (PS) or DOPC-PS mixture. After phenolic acid treatment, the negative charge of membranes increased in alkaline pH solutions, but not in acidic ones. The impedance data showed elevated values of both the electrical capacitance and the electrical resistance. We concluded that at acidic pH all tested compounds were able to solubilize into the membrane and permeate it. At neutral and alkaline pH, the CinA could be partially inserted into the bilayers, whereas p-CoA and FA could be anchored at the bilayer surface. Our results indicate that the electrochemical methods might be crucial for predicting pharmacological activity and bioavailability of phenolic acids.

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The Modulating Effect of p-Coumaric Acid on The Surface Charge Density of Human Glioblastoma Cell Membranes

Cited by 9 publications

References 46 publications

Monitoring of the Surface Charge Density Changes of Human Glioblastoma Cell Membranes upon Cinnamic and Ferulic Acids Treatment

Monitoring of the Surface Charge Density Changes of Human Glioblastoma Cell Membranes upon Cinnamic and Ferulic Acids Treatment

Biologically Active Compounds of Plants: Structure-Related Antioxidant, Microbiological and Cytotoxic Activity of Selected Carboxylic Acids

Electrophoretic Light Scattering and Electrochemical Impedance Spectroscopy Studies of Lipid Bilayers Modified by Cinnamic Acid and Its Hydroxyl Derivatives

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