Electrophoretic Light Scattering and Electrochemical Impedance Spectroscopy Studies of Lipid Bilayers Modified by Cinnamic Acid and Its Hydroxyl Derivatives
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 chemoprevent...
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MDPI AG
2020-11-01
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| Series: | Membranes |
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| Online Access: | https://www.mdpi.com/2077-0375/10/11/343 |
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| author | Monika Naumowicz Marcin Zając Magdalena Kusaczuk Miroslav Gál Joanna Kotyńska |
| author_facet | Monika Naumowicz Marcin Zając Magdalena Kusaczuk Miroslav Gál Joanna Kotyńska |
| author_sort | Monika Naumowicz |
| collection | DOAJ |
| description | 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), <i>p</i>-coumaric acid (<i>p</i>-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 <i>p</i>-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. |
| first_indexed | 2024-03-10T14:51:22Z |
| format | Article |
| id | doaj.art-f46d8efca0cb4edda7e4d5962aaafa51 |
| institution | Directory Open Access Journal |
| issn | 2077-0375 |
| language | English |
| last_indexed | 2024-03-10T14:51:22Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Membranes |
| spelling | doaj.art-f46d8efca0cb4edda7e4d5962aaafa512023-11-20T21:01:12ZengMDPI AGMembranes2077-03752020-11-01101134310.3390/membranes10110343Electrophoretic Light Scattering and Electrochemical Impedance Spectroscopy Studies of Lipid Bilayers Modified by Cinnamic Acid and Its Hydroxyl DerivativesMonika Naumowicz0Marcin Zając1Magdalena Kusaczuk2Miroslav Gál3Joanna Kotyńska4Department of Physical Chemistry, Faculty of Chemistry, University of Bialystok, K. Ciolkowskiego 1K, 15-245 Bialystok, PolandDoctoral School of Exact and Natural Sciences, University of Bialystok, K. Ciolkowskiego 1K, 15-245 Bialystok, PolandDepartment of Pharmaceutical Biochemistry, Medical University of Bialystok, Mickiewicza 2A, 15-222 Bialystok, PolandDepartment of Inorganic Technology, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, SlovakiaDepartment of Physical Chemistry, Faculty of Chemistry, University of Bialystok, K. Ciolkowskiego 1K, 15-245 Bialystok, PolandPharmacological 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), <i>p</i>-coumaric acid (<i>p</i>-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 <i>p</i>-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.https://www.mdpi.com/2077-0375/10/11/343cinnamic acid<i>p</i>-coumaric acidferulic acidphenolic compoundelectrophoretic light scatteringelectrochemical impedance spectroscopy |
| spellingShingle | Monika Naumowicz Marcin Zając Magdalena Kusaczuk Miroslav Gál Joanna Kotyńska Electrophoretic Light Scattering and Electrochemical Impedance Spectroscopy Studies of Lipid Bilayers Modified by Cinnamic Acid and Its Hydroxyl Derivatives Membranes cinnamic acid <i>p</i>-coumaric acid ferulic acid phenolic compound electrophoretic light scattering electrochemical impedance spectroscopy |
| title | Electrophoretic Light Scattering and Electrochemical Impedance Spectroscopy Studies of Lipid Bilayers Modified by Cinnamic Acid and Its Hydroxyl Derivatives |
| title_full | Electrophoretic Light Scattering and Electrochemical Impedance Spectroscopy Studies of Lipid Bilayers Modified by Cinnamic Acid and Its Hydroxyl Derivatives |
| title_fullStr | Electrophoretic Light Scattering and Electrochemical Impedance Spectroscopy Studies of Lipid Bilayers Modified by Cinnamic Acid and Its Hydroxyl Derivatives |
| title_full_unstemmed | Electrophoretic Light Scattering and Electrochemical Impedance Spectroscopy Studies of Lipid Bilayers Modified by Cinnamic Acid and Its Hydroxyl Derivatives |
| title_short | Electrophoretic Light Scattering and Electrochemical Impedance Spectroscopy Studies of Lipid Bilayers Modified by Cinnamic Acid and Its Hydroxyl Derivatives |
| title_sort | electrophoretic light scattering and electrochemical impedance spectroscopy studies of lipid bilayers modified by cinnamic acid and its hydroxyl derivatives |
| topic | cinnamic acid <i>p</i>-coumaric acid ferulic acid phenolic compound electrophoretic light scattering electrochemical impedance spectroscopy |
| url | https://www.mdpi.com/2077-0375/10/11/343 |
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