Synthesis and receptor binding of oxytocin analogs containing conformationally restricted amino acids |
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Authors: | Bakos Krisztina Havass Judit Fülöp Ferenc Gera Lajos Stewart John M Falkay George Tóth Gábor K |
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Institution: | 1.Department of Medical Chemistry, University of Szeged, Dóm tér 8, Szeged, Hungary ;2.Department of Pharmacy and Biopharmacy, University of Szeged, E?tv?s u. 6, Szeged, Hungary ;3.Department of Pharmaceutical Chemistry, University of Szeged, E?tv?s u. 6, Szeged, Hungary ;4.Department of Biochemistry and Molecular Genetics, University of Colorado School of Medicine, U.S.A ;5.Department of Medical Chemistry, University of Szeged, Dóm tér 8, Szeged, Hungary ; |
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Abstract: | Summary 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 afterin vivo measurements of their inhibition of uterine motor activity. |
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Keywords: | α -(2-indanyl)glycine 1-methyltetrahydro-β -carboline 6-methoxy-2-aminotetralin carboxylic acid differently substituted phenylalanine analogs tocolysis |
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