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Search for "membranes" in Full Text gives 200 result(s) in Beilstein Journal of Organic Chemistry.
Effect of a photoswitchable rotaxane on membrane permeabilization across lipid compositions
Beilstein J. Org. Chem. 2025, 21, 2498–2512, doi:10.3762/bjoc.21.192
- ; membrane fluidity; membrane permeability; photoswitchable rotaxane; Introduction Lipid membranes play a vital role in biology by acting as protective barriers for cells and organelles while regulating the passage of substances. Additionally, their structure and dynamics influence the activity of membrane
- proteins that are responsible for essential cellular functions [1]. As a result, the function and properties of lipid membranes are significantly influenced by their lipid composition, which varies across various domains of life, including mammalian, prokaryotic, and plant cells, and even between
- organelles within the same cell [2]. Therefore, there is a great need to develop molecular tools capable of modulating membrane structure in a controlled manner, either to facilitate cargo transport (such as drug delivery) [3][4], to irreversibly disrupt membranes and induce cell death (e.g., for targeting
Rotaxanes with integrated photoswitches: design principles, functional behavior, and emerging applications
Beilstein J. Org. Chem. 2025, 21, 2345–2366, doi:10.3762/bjoc.21.179
- ring appended to it, capable of capturing K+ ions (Figure 6) [51]. The authors demonstrated that this rotaxane can be incorporated into model lipid bilayers and mediate K+ ion transport across membranes through the shuttling motion of the macrocycle. In its trans configuration, the azobenzene allows
- photoswitchable rotaxanes into lipid membranes has revealed exciting opportunities for future biooriented applications. These applications include light-controlled systems for drug release, ion transport, rotaxane-based therapeutics, and molecular tools capable of modulating biological processes in living cells
Research progress on calixarene/pillararene-based controlled drug release systems
Beilstein J. Org. Chem. 2025, 21, 1757–1785, doi:10.3762/bjoc.21.139
- mechanisms that will be detailed in this article, researchers have made progress in the transport of amino acids and molecular peptides across membranes using macrocycles in recent years [35][36][37]. These works have paved the way for the potential application of remote-controlled membrane transport
- technology in the field of hydrophilic functional biomolecules, and is expected to be applied to stimulus-responsive controlled drug transport across membranes in the future. Currently, various artificially synthesized macrocyclic hosts have found extensive applications in drug-controlled release systems
Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides
Beilstein J. Org. Chem. 2025, 21, 1671–1677, doi:10.3762/bjoc.21.131
- polysaccharide (PS A1) (1), which has been shown by Andreana et al. to significantly activate the immune system and therefore recognized as a promising candidate for cancer immunotherapy [2][3][4][5]. This distinct structure is crucial for regulating the transportation of substances across cell membranes and
4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches
Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65
- examined molecules was assessed via two key parameters: Caco-2 membrane permeability and intestinal absorption. Caco-2 membrane permeability is widely recognized as a critical indicator of a compound's ability to permeate biological membranes, in which permeability is measured in log Papp. A log Papp value
Origami with small molecules: exploiting the C–F bond as a conformational tool
Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54
- valuable property in the context of drug design, because chameleonic fluorinated molecules such as compounds 2 and 3 might be expected to pass more easily through cell membranes, a manoeuvre which requires some level of solubility in both aqueous and organic environments. Another consequence of introducing
Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia
Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23
- infections are associated with biofilm formation, respectively, including serious infections affecting mucosal membranes or on implants yielding serious threats in hospitalized patients [3][4]. Consequently, biofilm-based antibiotic resistance poses a major threat to human health and substantially
Hot shape transformation: the role of PSar dehydration in stomatocyte morphogenesis
Beilstein J. Org. Chem. 2025, 21, 47–54, doi:10.3762/bjoc.21.5
- membranes. In this example by Buscema et al. it was observed that liposome vesicles can deform under mechanical stress to yield similar structures as the PSar-PBLG vesicles [32]. It was attempted to change the shape of the assembled vesicles following a similar method as previously developed for PEG-PS
- into a stomatocyte as demonstrated in Figure 1. The progression of shape transformation was monitored from 0 to 120 seconds before quenching. Initially, upon heating and immediate quenching, typical vesicles were observed. This contrasted with earlier observations of wrinkled membranes, suggesting
Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions
Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231
- this study, we aim to develop a system to achieve a quick Vm control without damaging the membranes by using a C60 derivative and a pyrene derivative as a model system for the triad molecules. C60 has been reported to be incorporated into the phospholipid bilayers at the central part of membrane due to
- localized near the surface of phospholipid membranes [11][12]. With this model system, we aimed to examine whether both the intramembrane localization and the photodynamic actions of catC60 can be modulated by PyBA. Results and Discussion The catC60-loaded liposomes (catC60-lip) were prepared by hydration
- -6000 spectrofluorometer (Shimadzu Corporation, Kyoto, Japan) (excitation at 341 nm, emission at 360–500 nm) to evaluate the interaction between catC60 and PyBA in DMPC membranes. Measurements were also performed after the addition of 10 times the volume of methanol to the liposome samples to liberate
5th International Symposium on Synthesis and Catalysis (ISySyCat2023)
Beilstein J. Org. Chem. 2024, 20, 2704–2707, doi:10.3762/bjoc.20.227
- values in the range of 1–10 μM. Teixeira et al. reported the preparation of new triazinephosphonate-based dopants and their application in the production of Nafion proton exchange membranes, which exhibited higher conductivity with only 1 wt % loading [19]. These new triazinephosphonate dopants could
- significantly impact the production of enhanced Nafion membranes, contributing to the development of more efficient decarbonized energy systems based on hydrogen technologies. The six triazinephosphonate derivatives bearing 4-aminophenyl or 4-hydroxyphenyl groups were obtained in very good yields through a
- nucleophilic substitution reaction between cyanuric chloride and 4-aminophenylphosphonate or 4-hydroxyphenylphosphonate derivatives. These synthesized dopants were used to prepare the modified Nafion membranes using a casting methodology. Almodovar and Tomé reported the synthesis and characterization of nine
Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments
Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202
- compounds leads to an increased lipophilicity and, as a result, facilitates the transfer of the molecule through cell membranes to the target site [22]. 1,2,4-Triazole derivatives also play a key role in medicinal chemistry, especially in the development of new antivirals [23][24] and antibacterial agents
New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)
Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145
- applications and performances depend on key components such as their separators/ion-exchange membranes. The most studied and already commercialized Nafion membrane shows great chemical stability, but its water content limits its high proton conduction to a limited range of operating temperatures. Here, we
- report the synthesis of a new series of triazinephosphonate derivatives and their use as dopants in the preparation of new modified Nafion membranes. The triazinephosphonate derivatives were prepared by substitution of chlorine atoms in cyanuric chloride. Diverse conditions were used to obtain the
- trisubstituted (4-hydroxyphenyl)triazinephosphonate derivatives and the (4-aminophenyl)triazinephosphonate derivatives, but with these amino counterparts, only the disubstituted compounds were obtained. The new modified Nafion membranes were prepared by casting incorporation of the synthesized 1,3,5
The Ugi4CR as effective tool to access promising anticancer isatin-based α-acetamide carboxamide oxindole hybrids
Beilstein J. Org. Chem. 2024, 20, 1213–1220, doi:10.3762/bjoc.20.104
- derivatives were 8h and 8k. The former is an α,β-unsaturated amide, which could react with nucleophiles inside the cell and thus explain its relative potency. The latter bears a long aliphatic side chain (thirteen carbon atoms), which could allow anchoring to cell membranes, representing a potential target
Light on the sustainable preparation of aryl-cored dibromides
Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95
- molecular wires or extended structures – either linear or cyclic – with enhanced functionality. Consequently, they play a crucial role in the fabrication of polymers [4][5][6][7], cyclophanes [8], photoactive materials [9][10][11], membranes [12], and other architectures. The synthetic potential of aryl
Synthesis of new representatives of A3B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations
Beilstein J. Org. Chem. 2024, 20, 767–776, doi:10.3762/bjoc.20.70
- properties and to modify the profile of biological activity due to optimum fluorine lipophylic properties, and enhanced interaction with lipid membranes [12][13][14]. Pentafluorophenyl-substituted porphyrin systems are especially useful for the connection of various functionalities capable for coupling with
Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization
Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66
- brevis [27], can penetrate the lipid phase of a Gram-positive inner cell membrane [28][29]. Despite exhibiting high antimicrobial activity, this compound also disrupts the membranes of higher mammalian cells, as evidenced by their pronounced hemolytic activity [30]. Establishing a concise and diverse
Switchable molecular tweezers: design and applications
Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45
Development of a chemical scaffold for inhibiting nonribosomal peptide synthetases in live bacterial cells
Beilstein J. Org. Chem. 2024, 20, 445–451, doi:10.3762/bjoc.20.39
- differences in the composition of cell membranes and presence of efflux pumps [9]. Specific protein labeling using a chemical probe can help to identify, characterize, and visualize target proteins [10][11]. The first chemical probe used for A-domains in NRPSs was reported by Marahiel et al. [8]. They
Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration
Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115
- synthetic and biological membranes and therefore to induce an increase of membrane permeability. However, the effect of cholesterol (CHOL) content in the membrane on the CD permeabilizing effect was not considered yet. Given that an increase in CHOL content reduces the membrane permeability, the aim of this
- membranes; this effect increased with CDs concentration. Among the studied CDs, α-CD, β-CD, and RAMEB were the most permeabilizing CDs on the different membranes. Similar modifications of SRB release from the various liposomal formulations were obtained with HP-β-CD, CRYSMEB, and SBE-β-CD. γ-CD was the less
- fields, mainly in drug delivery where they are used as pharmaceutical excipients to increase the drug permeability through biological membranes improving drug bioavailability and efficacy [2][4][5]. Furthermore, the CDs peculiarities helped to develop a combined system in which CD–guest complexes are
Synthesis of ether lipids: natural compounds and analogues
Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96
- the endoplasmic reticulum (ER). Then, ELs are spread off in the cell, to the plasma membranes but also in other biomembranes (membrane of mitochondria, ER, nucleus). The occurrence of ELs in tissues was first assessed by Snyder and Woods who reported that neutral ELs and phosphoglycero ELs were
- bonding (present in diacyl glycero ether lipids) by an ether function has also some consequences on the biophysics of membranes. Two recent reviews by A. Koivuniemi [28] and by Jiménez-Rojo and Riezman [29] dedicated respectively to the effect of plasmalogen on biophysics of membranes and the molecular
- mainly assessed for PE-ELs, suggests that the presence of EL in biomembranes impacts their curvature. The effect of ELs on the biophysics of membranes suggests that ELs have an important role in some physiological phenomena like the sporulation processes of some prokaryotic cells [32], the epithelium to
Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors
Beilstein J. Org. Chem. 2023, 19, 1198–1215, doi:10.3762/bjoc.19.88
- of artificial photosynthesis research investigating the compartmentalization of different reactions using liposomes and membranes [38]. Another alternative could be to use redox-active polymers as recyclable donors which would allow microporous membrane separation. Redox-active polymers are a very
- active area of research for aqueous and non-aqueous RFBs [59][60]. This is because often the most expensive component of an RFB is the ion-exchange membrane used to prevent the mixing of charged species and recombination. Microporous membranes are much less expensive, and the particulate size of redox
- decoupled water-splitting studies are re-reduced using protons from water in acidic conditions, and are used to transport hydrogen equivalents across membranes and between reactors. Some examples have been used as recyclable reductants [58]. These particular quinones have low enough oxidation potentials for
Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87
- molecules that attack and destroy lipids and protein membranes of weed cells [10]. Fipronil is an inhibitor of GABA receptors and affects the nervous system of insects as a broad-spectrum insecticide [11][12]. On the other hand, thioamides are an important class of organic compounds. 6-Thioguanine and
Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities
Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59
- separated by 10% SDS-PAGE and transferred onto PVDF membranes. The membranes were blocked with 5% BSA and incubated with the indicated antibodies overnight at 4 °C. Following this, the membranes were incubated with horseradish peroxidase (HRP)-conjugated secondary antibody at room temperature. The ECL kit
Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme
Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40
- exhibited a micromolar and submicromolar binding affinity for ds-polynucleotides and inactivated a mutant of dipeptidyl peptidase enzyme E451A. Confocal microscopy revealed that the conjugate with the longer linker entered the HeLa cell membranes and blue fluorescence was visualized as the dye accumulated
- cellular uptake and intracellular distribution of Phen-Py-1 in HeLa cells by TCS SP8 X confocal microscopy. The results showed that the dye entered the HeLa cell membranes fast, and after 1 hour of incubation at 1 µM concentration, blue fluorescence was visualized as the dye accumulated in the cell
Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors
Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14
- hydrolyzed to the ineffective carboxylate form at basic pH, resulting in decreased clinical efficacy and increased drug-related toxicity. As only the lactone structure of CPT can be transferred through cellular membranes and inhibit topoisomerase I, it is the functional component of CPT lactone form that is
- our group, and detailed studies were carried out to elucidate the mechanism. Both the results of our studies and the literature emphasize that cyclodextrins show high affinity for lipid-based molecules such as cholesterol and phospholipids in biological membranes [50][55][56]. Furthermore, it was
- recent study, cellular cholesterol is directly involved in T cell-mediated cytotoxicity. Cancer cells with cholesterol-rich plasma membranes can evade the immune system by blocking toxicity caused by T cells, but as the amount of cholesterol in the tumor decreases, T cell-mediated cytotoxicity rises [72
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