ArticleJournal of medicinal chemistry2024
Chromatographic Determination of Permeability-Relevant Lipophilicity Facilitates Rapid Analysis of Macrocyclic Peptide Scaffolds.
Article in Journal of medicinal chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
8 citing papers in PubMed.
- Backbone Steric Constraints Underlie High Passive Membrane Permeability of N-Alkyl Peptides.Angewandte Chemie (International ed. in English) · 2026Article
- A fast high-throughput logP estimation method for peptide molecules based on liquid chromatography-mass spectrometry method.Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents · 2026Article
- The Biggest Challenge for Prediction of Membrane Permeability of Cyclic Peptides: Scarce Data Availability.Journal of medicinal chemistry · 2026Article
- A diverse and chemically relevant solvation model benchmark set with flexible molecules and conformer ensembles.Chemical science · 2025Article
- Hydrogel-Bead Particles Enable Activity-Based Identification of Nucleic Acid Aptamer Enzyme Inhibitors.Analytical chemistry · 2025Article
- Trimetazidine-Profen Hybrid Molecules: Synthesis, Chemical Characterization, and Biological Evaluation of Their Racemates.Pharmaceuticals (Basel, Switzerland) · 2025Article
- Review
- Synthesis of Novel Benzothiazole-Profen Hybrid Amides as Potential NSAID Candidates.Molecules (Basel, Switzerland) · 2024Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
Hydrocarbon-determined shake-flask measurements have demonstrated great utility for optimizing lipophilicity during early drug discovery. Alternatively, chromatographic methods confer reduced experimental error and improved handling of complex mixtures. In this study, we developed a chromatographic approach for estimating hydrocarbon-water shake-flask partition coefficients for a variety of macrocyclic peptides and other bRo5 molecules including PROTACs. The model accurately predicts experimental shake-flask measurements with high reproducibility across a wide range of lipophilicities. The chromatographic retention times revealed subtle conformational effects and correlated with the ability to sequester hydrogen bond donors in low dielectric media. Estimations of shake-flask lipophilicity from our model also accurately predicted trends in MDCK passive cell permeability for a variety of thioether-cyclized decapeptides. This method provides a convenient, high-throughput approach for measuring lipophilic permeability efficiency and predicting passive cell permeability in bRo5 compounds that is suitable for multiplexing pure compounds or investigating the properties of complex library mixtures.
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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 Socratic graph.