N-alkylated dipeptide amides and related structures as imitations of the melanocortins' active core

Mutulis, Felikss (author): Uppsala universitet,Avdelningen för farmaceutisk farmakologi,Proteochemometric group

Mutule, Ilze (author): Uppsala universitet,Avdelningen för farmaceutisk farmakologi,Proteochemometric group

Liepinsh, Edvards (author)

Yahorau, Aleh (author): Uppsala universitet,Avdelningen för farmaceutisk farmakologi,Proteochemometric group

Lapinsh, Maris (author): Uppsala universitet,Avdelningen för farmaceutisk farmakologi,Proteochemometric group

Kopantshuk, Sergei (author): Uppsala universitet,Avdelningen för farmaceutisk farmakologi,Proteochemometric group

Veiksina, Santa (author): Uppsala universitet,Avdelningen för farmaceutisk farmakologi,Proteochemometric group

Rinken, Ago (author)

Wikberg, Jarl E S (author): Uppsala universitet,Avdelningen för farmaceutisk farmakologi,Proteochemometric group

(creator_code:org_t)

Elsevier BV, 2005
2005
English.
In: Peptides. - : Elsevier BV. - 0196-9781 .- 1873-5169. ; 26:10, s. 1997-2016

Related links:: https://urn.kb.se/re...; show more...; https://doi.org/10.1...; http://kipublication...; show less...

Abstract Subject headings

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.

By the author/editor: Mutulis, Felikss; Mutule, Ilze; Liepinsh, Edvard ...; Yahorau, Aleh; Lapinsh, Maris; Kopantshuk, Serg ...; show more...; Veiksina, Santa; Rinken, Ago; Wikberg, Jarl E ...; show less...

About the subject

MEDICAL AND HEALTH SCIENCES: MEDICAL AND HEAL ...; and Basic Medicine; and Pharmaceutical S ...

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