ArticleAngewandte Chemie (International ed. in English)2022
Tuning Electrostatic and Hydrophobic Surfaces of Aromatic Rings to Enhance Membrane Association and Cell Uptake of Peptides.
Article in Angewandte Chemie (International ed. in English), 2022. 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, 41 citations in OpenAlex.
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- Trifluoromethylthio and Trifluoromethyl Functionalization of Endomorphin-1 Enhances its Hydrophobicity and Plasma Stability while Preserving its Affinity for the μ-Opioid Receptor.The Journal of organic chemistry · 2026Article
- Advanced cell-derived drug delivery systems for pulmonary diseases: from bench to bedside.Drug delivery · 2025Review
- Phase-Separated Coacervates of Low-Molecular-Weight Compounds for Cytosolic Delivery and Disease Treatment.JACS Au · 2025Review
- High-performance electrochemical biosensor comprising Mn-ZIF-67 conjugated with anti-O antibody for Escherichia coli detection.Communications chemistry · 2025Article
- Peptide/Protein Functionalization and Macrocyclization via Alkyne Umpolung with Hypervalent Iodine Reagents.Accounts of chemical research · 2025Article
- Hydrophobic and Polarized Aromatic Residues Promote Internalization of Arg-Rich Cell-Penetrating Peptides through Ionpair-π Interactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Enzymatic Synthesis of Functional PEGylated Adipate Copolymers.ChemPlusChem · 2025Article
- DFT Investigations and Molecular Docking as Potent Inhibitors of SARS-CoV-2 Main Protease of Novel Pyrimidine Dione Derivatives.Biochemistry research international · 2025Article
- The Effect of Metformin and Hydrochlorothiazide on Cytochrome P450 3A4 Metabolism of Ivermectin: Insights from In Silico Experimentation.International journal of molecular sciences · 2024Article
- Cellular Uptake of Phase-Separating Peptide Coacervates.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Theoretical basis, state and challenges of living cell-based drug delivery systems.Theranostics · 2024Review
- Recognition and reprogramming of E3 ubiquitin ligase surfaces by α-helical peptides.Nature communications · 2023Article
- Trifluoromethylthiolation of Tryptophan and Tyrosine Derivatives: A Tool for Enhancing the Local Hydrophobicity of Peptides.The Journal of organic chemistry · 2023Article
- Genetically encoded discovery of perfluoroaryl macrocycles that bind to albumin and exhibit extended circulation in vivo.Nature communications · 2023Article
- Linearization of the Brevicidine and Laterocidine Lipopeptides Yields Analogues That Retain Full Antibacterial Activity.Journal of medicinal chemistry · 2023Article
- A focus on the discovery of potent and selective cyclic peptide scaffolds for drug development.Chemical science · 2022Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Aromatic groups are key mediators of protein-membrane association at cell surfaces, contributing to hydrophobic effects and π-membrane interactions. Here we show electrostatic and hydrophobic influences of aromatic ring substituents on membrane affinity and cell uptake of helical, cyclic and cell penetrating peptides. Hydrophobicity is important, but subtle changes in electrostatic surface potential, dipoles and polarizability also enhance association with phospholipid membranes and cell uptake. A combination of fluorine and sulfur substituents on an aromatic ring induces microdipoles that enhance cell uptake of 12-residue peptide inhibitors of p53-HDM2 interaction and of cell-penetrating cyclic peptides. These aromatic motifs can be readily inserted into peptide sidechains to enhance their cell uptake.
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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.