ArticleJournal of the American Chemical Society2010
Multiple N-methylation of MT-II backbone amide bonds leads to melanocortin receptor subtype hMC1R selectivity: pharmacological and conformational studies.
Article in Journal of the American Chemical Society, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 48 papers.
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Who cites it
48 citing papers in PubMed.
- Backbone N-Methylation Improves PPCA-Binding of a Stylissatin A Analogue via Conformational Modulation.Chemistry, an Asian journal · 2026Article
- Melanocortin 1 Receptor Regulates Pathological and Physiological Cardiac Remodeling.Journal of the American Heart Association · 2025Article
- Hepatocyte-specific loss of melanocortin 1 receptor disturbs fatty acid metabolism and promotes adipocyte hypertrophy.International journal of obesity (2005) · 2024Article
- Synthesis of Cyclopeptides Analogues of Natural Products and Evaluation as Herbicides and Inhibitors of Cyanobacteria.ACS omega · 2024Article
- α-Melanocyte-stimulating hormone alleviates pathological cardiac remodeling via melanocortin 5 receptor.EMBO reports · 2024Article
- Article
- Ribosomal incorporation of negatively charged d-α- andPhilosophical transactions of the Royal Society of London. Series B, Biological sciences · 2023Article
- Acyldepsipeptide Analogues: A Future Generation Antibiotics for Tuberculosis Treatment.Pharmaceutics · 2022Review
- Applying Promiscuous RiPP Enzymes to Peptide BackboneACS chemical biology · 2022Article
- Demonstration of a Common DPheJournal of medicinal chemistry · 2022Article
- Aged Brains Express Less Melanocortin Receptors, Which Correlates with Age-Related Decline of Cognitive Functions.Molecules (Basel, Switzerland) · 2021Article
- Influence ofMolecules (Basel, Switzerland) · 2021Article
- Biosynthetic Strategies for Macrocyclic Peptides.Molecules (Basel, Switzerland) · 2021Review
- Pursuing Orally Bioavailable Hepcidin Analogues via CyclicBiomedicines · 2021Article
- First total synthesis of versicotide A, B and C.RSC advances · 2020Article
- Article
- Diverse N-Substituted Azole-Containing Amino Acids as Building Blocks for Cyclopeptides.ACS omega · 2020Article
- Methodologies for Backbone Macrocyclic Peptide Synthesis Compatible With Screening Technologies.Frontiers in chemistry · 2020Review
- Understanding Cell Penetration of Cyclic Peptides.Chemical reviews · 2019Review
- Synthesis, Profiling, and in Vivo Evaluation of Cyclopeptides ContainingACS medicinal chemistry letters · 2019Article
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Authors and funding
8 authors.
Funding
Abstract
Multiple N-methylation is a novel technology to improve bioavailability of peptides and increase receptor subtype selectivity. This technique has been applied here to the superpotent but nonselective cyclic peptide MT-II. A library of all possible 31 backbone N-methylated derivatives has been synthesized and tested for binding and activation at melanocortin receptor subtypes 1, 3, 4, and 5. It turned out that selectivity is improved with every introduced N-methyl group, resulting in several N-methylated selective and potent agonists for the hMC1R. The most potent of these derivatives is N-methylated on four out of five amide bonds in the cyclic structure. Its solution structure indicates a strongly preferred backbone conformation that resembles other alpha-MSH analogs but possesses much less flexibility and in addition distinct differences in the spatial arrangement of individual amino acid side chains.
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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.