Selectivity of cyclic [D-Nal7] and [D-Phe7] substituted MSH analogues for the melanocortin receptor subtypes

Helgi B. Schiö, Ruta Muceniece, Felikss Mutulis, Peteris Prusis, Gunnar Lindeberg, Shubh D.s. Sharma, Victor J. Hiruby, Jarl E.S. Wikberg

Research output: Contribution to journalArticle

77 Scopus citations

Abstract

The binding of the 2 cyclic lactam MSH (4-10) analogues (MTII, SHU9119), and 5 cyclic [Cys4, Cys10]α-MSH analogues were tested on cells transiently expressing the human MC1, MC3, MC4 and MC5 receptors. The results indicate a differential importance of the C-terminal (Lys-Pro-Val) and N-terminal (Ser-Tyr-Ser) of cyclic [Cys4, Cys10]α-MSH analogues in binding to the MC receptor subtypes. Substitution of D-Phe7 by D-Nal(2')7 in both the cyclic lactam MSH (4-10) and the cyclic disulphide MSH (4-10) analogues resulted in a shift in favour of selectivity for the MC4 receptor; the disulphide analogue, [Cys4, D-Nal(2')7 Cys10]α-MSH (4-10) (HS9510), showing the highest selectivity for the MC4 receptor among all the substances tested. However, the cyclic lactams displayed an over all higher affinity for the MC receptors, than any of the cyclic disulphide MSH (4-10) analogues.

Original languageEnglish (US)
Pages (from-to)1009-1013
Number of pages5
JournalPeptides
Volume18
Issue number7
DOIs
StatePublished - Nov 26 1997

Keywords

  • HS9510
  • Ligand binding
  • MSH
  • MTII
  • Melanocortin receptor subtypes
  • SHU9119

ASJC Scopus subject areas

  • Biochemistry
  • Physiology
  • Endocrinology
  • Cellular and Molecular Neuroscience

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    Schiö, H. B., Muceniece, R., Mutulis, F., Prusis, P., Lindeberg, G., Sharma, S. D. S., Hiruby, V. J., & Wikberg, J. E. S. (1997). Selectivity of cyclic [D-Nal7] and [D-Phe7] substituted MSH analogues for the melanocortin receptor subtypes. Peptides, 18(7), 1009-1013. https://doi.org/10.1016/S0196-9781(97)00079-X