Synthesis and receptor binding of oxytocin analogs containing conformationally restricted amino acids

Krisztina Bakos, Judit Havass, F. Fülöp, Lajos Gera, John M. Stewart, G. Falkay, G. Tóth

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

We report the solid-phase synthesis and receptor-binding properties of eleven oxytocin analogs (Mpa-Xxx-Ile-Gln-Asn-Cys-Sar-Arg-Gly-NH2) containing non-coded amino acids in position 2: D-α- and L-α-(2-indanyl)glycine, R,S-6-methoxy-2-aminotetralin-2-carboxylic acid, D- and L-pentafluorophenylalanine, D, L-2,4-dimethylphenylalanine, D,L-2,4,6-trimethylphenylalanine, R,R- and S,S-1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylic acid and R- and S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid. Some of these amino acid analogs (2-indanylglycine and D-pentafluorophenylalanine) were earlier successfully applied for the synthesis of potent bradykinin antagonists [1,2]. Their receptor bindings were tested on isolated guinea-pig uterus, rat liver and rat kidney inner medulla plasma membranes. The extent of binding of the peptides to the oxytocin receptor was in several cases was even higher than that of the parent hormone (oxytocin). However, the real pharmacological value of these analogs can be evaluated only after in vivo measurements of their inhibition of uterine motor activity.

Original languageEnglish
Pages (from-to)35-40
Number of pages6
JournalLetters in Peptide Science
Volume8
Issue number1
DOIs
Publication statusPublished - 2002

Fingerprint

Oxytocin Receptors
Oxytocin
Carboxylic acids
Amino acids
Rats
Kidney Medulla
S 6
Amino Acids
Solid-Phase Synthesis Techniques
2,4-Dichlorophenoxyacetic Acid
Cell membranes
Liver
Uterus
Guinea Pigs
Motor Activity
Hormones
Cell Membrane
Pharmacology
Peptides
carboline-3-carboxylic acid

Keywords

  • α-(2-indanyl)glycine
  • 1-methyltetrahydro-β-carboline
  • 6-methoxy-2- aminotetralin carboxylic acid
  • Differently substituted phenylalanine analogs
  • Tocolysis

ASJC Scopus subject areas

  • Biochemistry

Cite this

Synthesis and receptor binding of oxytocin analogs containing conformationally restricted amino acids. / Bakos, Krisztina; Havass, Judit; Fülöp, F.; Gera, Lajos; Stewart, John M.; Falkay, G.; Tóth, G.

In: Letters in Peptide Science, Vol. 8, No. 1, 2002, p. 35-40.

Research output: Contribution to journalArticle

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