ArticleACS medicinal chemistry letters2016
Stereochemistry Balances Cell Permeability and Solubility in the Naturally Derived Phepropeptin Cyclic Peptides.
Article in ACS medicinal chemistry letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 61 citations in OpenAlex.
- Diastereomeric Branched-Ester dBET1 Analogs Exhibit Conformation-Dependent Differences in Passive Membrane Permeability.Journal of medicinal chemistry · 2026Article
- Selection and characterization of a peptide-based complement modulator targeting C1 of the innate immune system.RSC chemical biology · 2024Article
- Molecular Design of Cyclic Peptides with Cell Membrane Permeability and Development of MDMX-p53 Inhibitor.ACS medicinal chemistry letters · 2023Article
- Targeted Protein Degradation: Advances, Challenges, and Prospects for Computational Methods.Journal of chemical information and modeling · 2023Review
- Identification of Macrocyclic Peptide Families from Combinatorial Libraries Containing Noncanonical Amino Acids Using Cheminformatics and Bioinformatics Inspired Clustering.ACS chemical biology · 2023Article
- Lessons for Oral Bioavailability: How Conformationally Flexible Cyclic Peptides Enter and Cross Lipid Membranes.Journal of medicinal chemistry · 2023Article
- Research Progress on Small Molecular Inhibitors of the Type 3 Secretion System.Molecules (Basel, Switzerland) · 2022Review
- Navigating complex peptide structures using macrocycle conformational maps.RSC chemical biology · 2022Article
- A New Amino Acid for Improving Permeability and Solubility in Macrocyclic Peptides through Side Chain-to-Backbone Hydrogen Bonding.Journal of medicinal chemistry · 2022Article
- Performance evaluation of flexible macrocycle docking in AutoDock.QRB discovery · 2022Article
- Targeting bacterial pathogenesis by inhibiting virulence-associated Type III and Type IV secretion systems.Frontiers in cellular and infection microbiology · 2022Review
- Crossing of the Cystic Barriers ofMolecules (Basel, Switzerland) · 2021Article
- Identifying the Cellular Target of Cordyheptapeptide A and Synthetic Derivatives.ACS chemical biology · 2021Article
- Defining and navigating macrocycle chemical space.Chemical science · 2021Article
- Macrocycle Cell Permeability Measured by Solvation Free Energies in Polar and Apolar Environments.Journal of chemical information and modeling · 2020Article
- Substrate Plasticity of a Fungal Peptide α-ACS chemical biology · 2020Article
- Solubility prediction in the bRo5 chemical space: where are we right now?ADMET & DMPK · 2020Article
- Delivering bioactive cyclic peptides that target Hsp90 as prodrugs.Journal of enzyme inhibition and medicinal chemistry · 2019Article
- Conformation and Permeability: Cyclic Hexapeptide Diastereomers.Journal of chemical information and modeling · 2019Article
- Identification of Morpholino Thiophenes as Novel Mycobacterium tuberculosis Inhibitors, Targeting QcrB.Journal of medicinal chemistry · 2018Article
Corrections and comments
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Cyclic peptide (CP) natural products provide useful model systems for mapping "beyond-Rule-of-5" (bRo5) space. We identified the phepropeptins as natural product CPs with potential cell permeability. Synthesis of the phepropeptins and epimeric analogues revealed much more rapid cellular permeability for the natural stereochemical pattern. Despite being more cell permeable, the natural compounds exhibited similar aqueous solubility as the corresponding epimers, a phenomenon explained by solvent-dependent conformational flexibility among the natural compounds. When analyzing the polarity of the solution structures we found that neither the number of hydrogen bonds nor the total polar surface area accurately represents the solvation energies of the high and low dielectric conformations. This work adds to a growing number of natural CPs whose solvent-dependent conformational behavior allows for a balance between aqueous solubility and cell permeability, highlighting structural flexibility as an important consideration in the design of molecules in bRo5 chemical space.
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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.