ArticleJournal of medicinal chemistry2012
Predicting and improving the membrane permeability of peptidic small molecules.
Article in Journal of medicinal chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Who cites it
31 citing papers in PubMed.
- Engineering Enantiocomplementary Protoglobins for Stereoconvergent Construction ofJournal of the American Chemical Society · 2026Article
- Effect of carboxymethyl substitution position on urea interaction with carboxymethyl chitosan: a density functional theory study.Journal of molecular modeling · 2026Article
- Linker Engineering in Stapled Peptides for Enhanced Membrane Permeability: Screening and Optimization Strategies.International journal of molecular sciences · 2026Review
- Diastereomeric Branched-Ester dBET1 Analogs Exhibit Conformation-Dependent Differences in Passive Membrane Permeability.Journal of medicinal chemistry · 2026Article
- Synergistic optimizations of efficacy and membrane permeability of IRAK4 inhibitors: identifying new lead compounds for anti-inflammatory therapeutics.Journal of enzyme inhibition and medicinal chemistry · 2025Article
- Article
- An experimental and computational investigation of the cyclopentene-containing peptide-derived compounds: focus on pseudo-cyclic motifs via intramolecular interactions.Royal Society open science · 2024Article
- Protective Effects of Anethole inAntioxidants (Basel, Switzerland) · 2024Article
- Substitution-Induced Mechanistic Switching in SMolecules (Basel, Switzerland) · 2024Article
- Targeted Protein Degradation: Advances, Challenges, and Prospects for Computational Methods.Journal of chemical information and modeling · 2023Review
- DNA-Encoded Macrocyclic Peptide Libraries Enable the Discovery of a Neutral MDM2-p53 Inhibitor.ACS medicinal chemistry letters · 2023Article
- Lessons for Oral Bioavailability: How Conformationally Flexible Cyclic Peptides Enter and Cross Lipid Membranes.Journal of medicinal chemistry · 2023Article
- Steering New Drug Discovery Campaigns: Permeability, Solubility, and Physicochemical Properties in the bRo5 Chemical Space.ACS medicinal chemistry letters · 2021Article
- The importance of intramolecular hydrogen bonds on the translocation of the small drug piracetam through a lipid bilayer.RSC advances · 2020Article
- Prediction of Passive Membrane Permeability by Semi-Empirical Method Considering Viscous and Inertial Resistances and Different Rates of Conformational Change and Diffusion.Molecular informatics · 2020Article
- Incorporation of an intramolecular hydrogen bonding motif in the side chain of antimalarial benzimidazoles.MedChemComm · 2019Article
- Emerging Methods and Design Principles for Cell-Penetrant Peptides.Angewandte Chemie (International ed. in English) · 2018Review
- Group-Based Optimization of Potent and Cell-Active Inhibitors of the von Hippel-Lindau (VHL) E3 Ubiquitin Ligase: Structure-Activity Relationships Leading to the Chemical Probe (2S,4R)-1-((S)-2-(1-Cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (VH298).Journal of medicinal chemistry · 2018Article
- Modulation of Oral Bioavailability and Metabolism for Closely Related Cyclic Hexapeptides.International journal of peptide research and therapeutics · 2018Article
- Two-track virtual screening approach to identify both competitive and allosteric inhibitors of human small C-terminal domain phosphatase 1.Journal of computer-aided molecular design · 2017Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
We evaluate experimentally and computationally the membrane permeability of matched sets of peptidic small molecules bearing natural or bioisosteric unnatural amino acids. We find that the intentional introduction of hydrogen bond acceptor-donor pairs in such molecules can improve membrane permeability while retaining or improving other favorable drug-like properties. We employ an all-atom force field based method to calculate changes in free energy associated with the transfer of the peptidic molecules from water to membrane. This computational method correctly predicts rank order experimental permeability trends within congeneric series and is much more predictive than calculations (e.g., clogP) that do not consider three-dimensional conformation.
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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.