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Prospects for Application of Natural Compounds and Their Derivatives in Biological and Artificial Membranes

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Special Issue Information
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A special issue of Membranes (ISSN 2077-0375). This special issue belongs to the section "Biological Membrane Functions".

Deadline for manuscript submissions: closed (20 November 2023) | Viewed by 16984

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Special Issue Editors

Dr. Mikhail Dubinin

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Guest Editor

Department of Biochemistry, Cell Biology and Microbiology, Mari State University, Yoshkar-Ola, Russia
Interests: biochemistry; biophysics; mitochondria; membranes; myopathy; liposomes; lipids; oxidative stress
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Konstantin Belosludtsev

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Guest Editor

Institute of Theoretical and Experimental Biophysics, Russian Academy of Sciences, Institutskaya 3, 142290 Pushchino, Russia
Interests: mitochondria; biophysics; diabetes mellitus; myopathy; mitochondrial Ca²⁺ transport; permeability transition pore; oxidative stress; reactive oxygen species; lipids; membrane proteins; liposomes
Special Issues, Collections and Topics in MDPI journals

Dr. Anna Spivak

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Guest Editor

Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Prospekt Oktyabrya 141, Ufa, Russia
Interests: natural products; terpenoids; polyphenol acids; medicine chemistry; mitochondria; mitochondria-targeting derivatives; antitumor activity; antioxidant activity

Special Issue Information

Dear Colleagues,

Natural substances began to play an increasing role in the discovery and development of new drugs. The possibilities of modern synthetic chemistry make it possible to perform a fine modification of natural precursors to create molecules that have a specific, targeted effect on various cellular structures. A popular direction in this area is the creation of agents capable of modifying the state and behavior of both biological and artificial membrane systems. The successful development of this area of biomedicine and pharmacology is due to the rapid development of modern experimental or computational methods including, but not limited to, those with Cryo-EM, AFM, diffraction, NMR, computer simulations, or biochemistry aimed at membrane-associated or membrane-embedded proteins or model membrane systems. This allows you to quickly create new promising therapeutic agents for the treatment of a wide range of socially significant and orphan diseases caused by dysfunction of membrane systems or requiring targeted drug delivery using modified membrane vesicles.

This Special Issue focuses on the latest advances in membrane-targeted biomedicine and pharmacology based on the use of natural compounds and their derivatives. We invite you to submit original research articles and reviews. Research areas may include (but are not limited to) the following:

Synthesis of new membrane-targeted molecules based on natural compounds and study of their effect on biological membranes and structures;
Development of new approaches for modifying artificial lipid membranes for their use in biomedicine and pharmacology.

We look forward to receiving your contributions.

Dr. Mikhail Dubinin
Prof. Dr. Konstantin Belosludtsev
Dr. Anna Yu. Spivak
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Membranes is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

biological membranes
artificial lipid membranes
natural compounds
synthetic chemistry
model membrane systems
membrane fluidity and composition
membrane dynamics
membrane permeability
membrane signaling and receptors
membrane channels
protein–lipid interactions
membrane biomedical applications
antitumor activity
antioxidant activity

Published Papers (6 papers)

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Research

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13 pages, 2650 KiB

Open AccessArticle

Triggering the Amphotericin B Pore-Forming Activity by Phytochemicals

by Svetlana S. Efimova, Anna I. Malykhina and Olga S. Ostroumova

Membranes 2023, 13(7), 670; https://doi.org/10.3390/membranes13070670 - 14 Jul 2023

Cited by 2 | Viewed by 1166

Abstract

The macrolide polyene antibiotic amphotericin B (AmB), remains a valuable drug to treat systemic mycoses due to its wide antifungal activity and low probability of developing resistance. The high toxicity of AmB, expressed in nephropathy and hemolysis, could be partially resolved by lowering therapeutic AmB concentration while maintaining efficacy. This work discusses the possibility of using plant polyphenols and alkaloids to enhance the pore-forming and consequently antifungal activity of AmB. We demonstrated that phloretin, phlorizin, naringenin, taxifolin, quercetin, biochanin A, genistein, resveratrol, and quinine led to an increase in the integral AmB-induced transmembrane current in the bilayers composed of palmitoyloleoylphosphocholine and ergosterol, while catechin, colchicine, and dihydrocapsaicin did not practically change the AmB activity. Cardamonin, 4′-hydroxychalcone, licochalcone A, butein, curcumin, and piperine inhibited AmB-induced transmembrane current. Absorbance spectroscopy revealed no changes in AmB membrane concentration with phloretin addition. A possible explanation of the potentiation is related to the phytochemical-produced changes in the elastic membrane properties and the decrease in the energy of formation of the lipid mouth of AmB pores, which is partially confirmed by differential scanning microcalorimetry. The possibility of AmB interaction with cholesterol in the mammalian cell membranes instead of ergosterol in fungal membranes, determines its high toxicity. The replacement of ergosterol with cholesterol in the membrane lipid composition led to a complete loss or a significant decrease in the potentiating effects of tested phytochemicals, indicating low potential toxicity of these compounds and high therapeutic potential of their combinations with the antibiotic. The discovered combinations of AmB with plant molecules that enhance its pore-forming ability in ergosterol-enriched membranes, seem to be promising for further drug development in terms of the toxicity decrease and efficacy improvement. Full article

(This article belongs to the Special Issue Prospects for Application of Natural Compounds and Their Derivatives in Biological and Artificial Membranes)

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15 pages, 4462 KiB

Open AccessArticle

Conformational State of Fenamates at the Membrane Interface: A MAS NOESY Study

by Ilya A. Khodov, Konstantin V. Belov, Daniel Huster and Holger A. Scheidt

Membranes 2023, 13(6), 607; https://doi.org/10.3390/membranes13060607 - 17 Jun 2023

Cited by 2 | Viewed by 9193

Abstract

The present work analyzes the ¹H NOESY MAS NMR spectra of three fenamates (mefenamic, tolfenamic, and flufenamic acids) localized in the lipid–water interface of phosphatidyloleoylphosphatidylcholine (POPC) membranes. The observed cross-peaks in the two-dimensional NMR spectra characterized intramolecular proximities between the hydrogen atoms of the fenamates as well as intermolecular interactions between the fenamates and POPC molecules. The peak amplitude normalization for an improved cross-relaxation (PANIC) approach, the isolated spin-pair approximation (ISPA) model, and the two-position exchange model were used to calculate the interproton distances indicative of specific conformations of the fenamates. The results showed that the proportions of the A+C and B+D conformer groups of mefenamic and tolfenamic acids in the presence of POPC were comparable within the experimental error and amounted to 47.8%/52.2% and 47.7%/52.3%, respectively. In contrast, these proportions for the flufenamic acid conformers differed and amounted to 56.6%/43.4%. This allowed us to conclude that when they bind to the POPC model lipid membrane, fenamate molecules change their conformational equilibria. Full article

(This article belongs to the Special Issue Prospects for Application of Natural Compounds and Their Derivatives in Biological and Artificial Membranes)

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18 pages, 1707 KiB

Open AccessArticle

Analysis of the Polyphenolic Composition of Vaccinium L. Extracts and Their Protective Effect on Red Blood Cell Membranes

by Teresa Kaźmierczak, Dorota Bonarska-Kujawa, Katarzyna Męczarska, Sylwia Cyboran-Mikołajczyk, Jan Oszmiański and Ireneusz Kapusta

Membranes 2023, 13(6), 589; https://doi.org/10.3390/membranes13060589 - 07 Jun 2023

Cited by 1 | Viewed by 1193

Abstract

The blueberry fruit of the genus Vaccinium, including high blueberry, low blueberry, and wild bilberry, is consumed for its flavor and medicinal properties. The purpose of the experiments was to investigate the protective effect and mechanism of the interaction of blueberry fruit polyphenol extracts with the erythrocytes and their membranes. The content of polyphenolic compounds in the extracts was determined using the chromatographic UPLC–ESI–MS method. The effects of the extracts on red blood cell shape changes, hemolysis and osmotic resistance were examined. Changes in the order of packing and fluidity of the erythrocyte membrane and the lipid membrane model caused by the extracts were identified using fluorimetric methods. Erythrocyte membrane oxidation was induced by two agents: AAPH compound and UVC radiation. The results show that the tested extracts are a rich source of low molecular weight polyphenols that bind to the polar groups of the erythrocyte membrane, changing the properties of its hydrophilic area. However, they practically do not penetrate the hydrophobic part of the membrane and do not damage its structure. Research results suggest that the components of the extracts can defend the organism against oxidative stress if they are delivered to the organism in the form of dietary supplements. Full article

(This article belongs to the Special Issue Prospects for Application of Natural Compounds and Their Derivatives in Biological and Artificial Membranes)

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16 pages, 2862 KiB

Open AccessArticle

Conjugation of Triterpenic Acids of Ursane and Oleanane Types with Mitochondria-Targeting Cation F16 Synergistically Enhanced Their Cytotoxicity against Tumor Cells

by Mikhail V. Dubinin, Darya A. Nedopekina, Anna I. Ilzorkina, Alena A. Semenova, Vyacheslav A. Sharapov, Eldar V. Davletshin, Natalia V. Mikina, Yuri P. Belsky, Anna Yu. Spivak, Vladimir S. Akatov, Natalia V. Belosludtseva, Jiankang Liu and Konstantin N. Belosludtsev

Membranes 2023, 13(6), 563; https://doi.org/10.3390/membranes13060563 - 30 May 2023

Cited by 3 | Viewed by 1815

Abstract

The present work shows the cytotoxic effects of novel conjugates of ursolic, oleanolic, maslinic, and corosolic acids with the penetrating cation F16 on cancer cells (lung adenocarcinoma A549 and H1299, breast cancer cell lines MCF-7 and BT474) and non-tumor human fibroblasts. It has been established that the conjugates have a significantly enhanced toxicity against tumor-derived cells compared to native acids and also demonstrate selectivity to some cancer cells. The toxic effect of the conjugates is shown to be due to ROS hyperproduction in cells, induced by the effect on mitochondria. The conjugates caused dysfunction of isolated rat liver mitochondria and, in particular, a decrease in the efficiency of oxidative phosphorylation, a decrease in the membrane potential, and also an overproduction of ROS by organelles. The paper discusses how the membranotropic- and mitochondria-targeted effects of the conjugates may be related to their toxic effects. Full article

(This article belongs to the Special Issue Prospects for Application of Natural Compounds and Their Derivatives in Biological and Artificial Membranes)

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24 pages, 4537 KiB

Open AccessArticle

3-Amino-Substituted Analogues of Fusidic Acid as Membrane-Active Antibacterial Compounds

by Elena V. Salimova, Oleg S. Mozgovoj, Svetlana S. Efimova, Olga S. Ostroumova and Lyudmila V. Parfenova

Membranes 2023, 13(3), 309; https://doi.org/10.3390/membranes13030309 - 07 Mar 2023

Cited by 2 | Viewed by 1468

Abstract

Fusidic acid (FA) is an antibiotic with high activity against Staphylococcus aureus; it has been used in clinical practice since the 1960s. However, the narrow antimicrobial spectrum of FA limits its application in the treatment of bacterial infections. In this regard, this work aims both at the study of the antimicrobial effect of a number of FA amines and at the identification of their potential biological targets. In this way, FA analogues containing aliphatic and aromatic amino groups and biogenic polyamine, spermine and spermidine, moieties at the C-3 atom, were synthesized (20 examples). Pyrazinecarboxamide-substituted analogues exhibit a high antibacterial activity against S. aureus (MRSA) with MIC ≤ 0.25 μg/mL. Spermine and spermidine derivatives, along with activity against S. aureus, also inhibit the growth and reproduction of Gram-negative bacteria Escherichia coli, Acinetobacter baumannii, and Pseudomonas aeruginosa, and have a high fungicidal effect against Candida albicans and Cryptococcus neoformans. The study of the membrane activity demonstrated that the spermidine- and spermine-containing compounds are able to immerse into membranes and disorder the lipidsleading to a detergent effect. Moreover, spermine-based compounds are also able to form ion-permeable pores in the lipid bilayers mimicking the bacterial membranes. Using molecular docking, inhibition of the protein synthesis elongation factor EF-G was proposed, and polyamine substituents were shown to make the greatest contribution to the stability of the complexes of fusidic acid derivatives with biological targets. This suggests that the antibacterial effect of the obtained compounds may be associated with both membrane activity and inhibition of the elongation factor EF-G. Full article

(This article belongs to the Special Issue Prospects for Application of Natural Compounds and Their Derivatives in Biological and Artificial Membranes)

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Review

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14 pages, 1313 KiB

Open AccessReview

Bile Acids as Inducers of Protonophore and Ionophore Permeability of Biological and Artificial Membranes

by Victor N. Samartsev, Ekaterina I. Khoroshavina, Evgeniya K. Pavlova, Mikhail V. Dubinin and Alena A. Semenova

Membranes 2023, 13(5), 472; https://doi.org/10.3390/membranes13050472 - 28 Apr 2023

Cited by 1 | Viewed by 1383

Abstract

It is now generally accepted that the role of bile acids in the organism is not limited to their participation in the process of food digestion. Indeed, bile acids are signaling molecules and being amphiphilic compounds, are also capable of modifying the properties of cell membranes and their organelles. This review is devoted to the analysis of data on the interaction of bile acids with biological and artificial membranes, in particular, their protonophore and ionophore effects. The effects of bile acids were analyzed depending on their physicochemical properties: namely the structure of their molecules, indicators of the hydrophobic–hydrophilic balance, and the critical micelle concentration. Particular attention is paid to the interaction of bile acids with the powerhouse of cells, the mitochondria. It is of note that bile acids, in addition to their protonophore and ionophore actions, can also induce Ca²⁺-dependent nonspecific permeability of the inner mitochondrial membrane. We consider the unique action of ursodeoxycholic acid as an inducer of potassium conductivity of the inner mitochondrial membrane. We also discuss a possible relationship between this K⁺ ionophore action of ursodeoxycholic acid and its therapeutic effects. Full article

(This article belongs to the Special Issue Prospects for Application of Natural Compounds and Their Derivatives in Biological and Artificial Membranes)

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