ArticleJournal of the American Chemical Society2020
Macrocyclic Modalities Combining Peptide Epitopes and Natural Product Fragments.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 49 citations in OpenAlex.
- Overcoming Ligand Discovery Challenges: Developing Peptide-Based Tracers for SPSB2.ACS chemical biology · 2026Article
- Small-Molecule Trk Agonists: Where Do We Go from Here?Journal of medicinal chemistry · 2025Review
- Discovery of a Series of Macrocycles as Potent Inhibitors ofJournal of medicinal chemistry · 2024Article
- Selective, Intrinsically Fluorescent Trk Modulating Probes.ACS chemical neuroscience · 2024Article
- Identification of macrocyclic peptides which activate bacterial cylindrical proteases.RSC medicinal chemistry · 2023Article
- pIChemiSt ─ Free Tool for the Calculation of Isoelectric Points of Modified Peptides.Journal of chemical information and modeling · 2023Article
- Synthesis of 20-Membered Macrocyclic Pseudo-Natural Products Yields Inducers of LC3 Lipidation.Angewandte Chemie (International ed. in English) · 2022Article
- Development of superior antibodies against the S-protein of SARS-Cov-2 using macrocyclic epitopes.Arabian journal of chemistry · 2022Article
- Recent Advances in Macrocyclic Drugs and Microwave-Assisted and/or Solid-Supported Synthesis of Macrocycles.Molecules (Basel, Switzerland) · 2022Review
- In Silico Analysis of Peptide Macrocycle -Protein Interactions.Methods in molecular biology (Clifton, N.J.) · 2022Article
- Macrocyclization strategies for cyclic peptides and peptidomimetics.RSC medicinal chemistry · 2021Review
- Anchor extension: a structure-guided approach to design cyclic peptides targeting enzyme active sites.Nature communications · 2021Article
- Chiral figure-eight molecular scaffold for fluorescent probe development.Organic & biomolecular chemistry · 2021Article
- Strategies to expand peptide functionality through hybridisation with a small molecule component.RSC chemical biology · 2021Review
- Modulating Protein-Protein Interactions by Cyclic and Macrocyclic Peptides. Prominent Strategies and Examples.Molecules (Basel, Switzerland) · 2021Review
Corrections and comments
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Authors and funding
12 authors at 5 institutions in 4 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
"Hot loop" protein segments have variable structure and conformation and contribute crucially to protein-protein interactions. We describe a new hot loop mimicking modality, termed PepNats, in which natural product (NP)-inspired structures are incorporated as conformation-determining and -restricting structural elements into macrocyclic hot loop-derived peptides. Macrocyclic PepNats representing hot loops of inducible nitric oxide synthase (iNOS) and human agouti-related protein (AGRP) were synthesized on solid support employing macrocyclization by imine formation and subsequent stereoselective 1,3-dipolar cycloaddition as key steps. PepNats derived from the iNOS DINNN hot loop and the AGRP RFF hot spot sequence yielded novel and potent ligands of the SPRY domain-containing SOCS box protein 2 (SPSB2) that binds to iNOS, and selective ligands for AGRP-binding melanocortin (MC) receptors. NP-inspired fragment absolute configuration determines the conformation of the peptide part responsible for binding. These results demonstrate that combination of NP-inspired scaffolds with peptidic epitopes enables identification of novel hot loop mimics with conformationally constrained and biologically relevant structure.
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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.