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N-alkylated dipeptide amides and related structures as imitations of the melanocortins' active core
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences, Pharmaceutical Pharmacology. (Proteochemometric group)
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences, Pharmaceutical Pharmacology. (Proteochemometric group)
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences, Pharmaceutical Pharmacology. (Proteochemometric group)
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2005 (English)In: Peptides, ISSN 0196-9781, E-ISSN 1873-5169, Vol. 26, no 10, 1997-2016 p.Article in journal (Refereed) Published
Abstract [en]

Thirty-three low molecular mass structures combining both peptide and peptoid features were prepared and tested on human melanocortin receptors MC1,3-5R. Most of them displayed low micromolar activity with preference for diamines, guanidino and 2-naphthyl derivatives compared to monoacetylated, amino and 3-indolyl counterparts. Some contained L- or D-histidine residues, but the change did not influence affinity. QSAR modelling yielded excellent models for the MC3-5 receptors explaining R2Y=0.89-0.91 and predicting Q2=0.77-0.80 of the affinity variations. One compound displayed MC1R selectivity (13-fold and more). An NMR study of showed that it exists as a mixture of four rotamers at its tertiary amide bonds. Comparisons with earlier data for melanocortin core tetrapeptide analogues indicate that the novel peptide-peptoids interact with the melanocortin receptors in a different way.

Place, publisher, year, edition, pages
2005. Vol. 26, no 10, 1997-2016 p.
Keyword [en]
Melanocortins, Peptidomimetics, Peptoid–peptide hybrids, Solid phase organic synthesis, Structure–activity, QSAR, NMR
National Category
Pharmaceutical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-104278DOI: 10.1016/j.peptides.2004.11.026PubMedID: 15985308OAI: oai:DiVA.org:uu-104278DiVA: diva2:219588
Available from: 2009-05-28 Created: 2009-05-28 Last updated: 2010-05-26Bibliographically approved

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