ArticleBiophysical journal2008
Distribution and dynamics of adamantanes in a lipid bilayer.
Article in Biophysical journal, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Bacterial Transformation of Adamantane and Its Derivatives: Regioselectivity and Biocatalytic Approaches.Biology · 2025Review
- Molecular biophysics and inhibition mechanism of influenza virus A M2 viroporin by adamantane-based drugs - Challenges in designing antiviral agents.Journal of structural biology: X · 2025Article
- Engineering Lipophilic Aggregation of Adapalene and Adamantane-Based Cocrystals via van der Waals Forces and Hydrogen Bonding.Crystal growth & design · 2024Article
- Silver Coordination Polymers Driven by Adamantoid Blocks for Advanced Antiviral and Antibacterial Biomaterials.ACS applied materials & interfaces · 2024Article
- 1,3-Dichloroadamantyl-Containing Ureas as Potential Triple Inhibitors of Soluble Epoxide Hydrolase, p38 MAPK and c-Raf.International journal of molecular sciences · 2023Article
- Rational synthesis of elusive organic-inorganic hybrid metal-oxo clusters: formation and post-functionalization of hexavanadates.Chemical science · 2023Article
- Inhibition of NMDA receptors through a membrane-to-channel path.Nature communications · 2022Article
- Effects of Cholesterol on the Partitioning of a Drug Molecule in Lipid Bilayers.The journal of physical chemistry. B · 2021Article
- Adamantane Containing Peptidoglycan Fragments Enhance RANTES and IL-6 Production in Lipopolysaccharide-Induced Macrophages.Molecules (Basel, Switzerland) · 2020Article
- Effects of MgNeuropharmacology · 2018Article
- Article
- Adamantane in Drug Delivery Systems and Surface Recognition.Molecules (Basel, Switzerland) · 2017Review
- Probing Lipophilic Adamantyl Group as the P1-Ligand for HIV-1 Protease Inhibitors: Design, Synthesis, Protein X-ray Structural Studies, and Biological Evaluation.Journal of medicinal chemistry · 2016Article
- Permeability of the Blood-Brain Barrier: Molecular Mechanism of Transport of Drugs and Physiologically Important Compounds.The Journal of membrane biology · 2015Review
- Structural effects and translocation of doxorubicin in a DPPC/Chol bilayer: the role of cholesterol.Biophysical journal · 2011Article
- Mechanism of inhibition of enveloped virus membrane fusion by the antiviral drug arbidol.PloS one · 2011Article
- Targeting cell entry of enveloped viruses as an antiviral strategy.Molecules (Basel, Switzerland) · 2010Review
- Partitioning and localization of environment-sensitive 2-(2'-pyridyl)- and 2-(2'-pyrimidyl)-indoles in lipid membranes: a joint refinement using fluorescence measurements and molecular dynamics simulations.The journal of physical chemistry. B · 2010Article
- NMR structure and ion channel activity of the p7 protein from hepatitis C virus.The Journal of biological chemistry · 2010Article
- Where does amantadine bind to the influenza virus M2 proton channel?Trends in biochemical sciences · 2010Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The adamantanes are a class of compounds that have found use in the treatment of influenza A and Parkinson's disease, among others. The mode of action for influenza A is based on the adamantanes' interaction with the transmembrane M2 channel, whereas the treatment of Parkinson's disease is thought to relate to a channel block of N-methyl-D-aspartate receptors. An understanding of how these compounds interact with the lipid bilayer is thus of great interest. We used molecular-dynamics simulations to calculate the potential of mean force of adamantanes in a lipid bilayer. Our results demonstrate a preference for the interfacial region of the lipid bilayer for both protonated and deprotonated species, with the protonated species proving significantly more favorable. However, the protonated species have a large free-energy barrier in the center of the membrane. In contrast, there is no barrier (compared with aqueous solution) at the center of the bilayer for deprotonated species, suggesting that the permeant species is indeed the neutral form, as commonly assumed. We discuss the results with respect to proposed mechanisms of action and implications for drug-delivery in general.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.