Synthesis of oxytocin antagonists containing conformationally constrained amino acids in position 2

Tóth, Gábor; Bakos, K.; Penke, Botond; Pávó, Imre; Varga, Csaba; Török, G.; Péter, Antal; Fülöp, Ferenc

doi:10.1016/s0960-894x(99)00041-4

Cited by 21 publications

(2 citation statements)

References 23 publications

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“…[15][16][17] They can also be used as building blocks in modified analogues of pharmacologically active peptides. [18][19][20] Conformational studies of β-amino acid oligomers are also currently at the focus of interest. [21][22][23][24] Besides their diverse chemical compositions, β-amino acids and their derivatives possess noteworthy pharmacological effects; for example, (1R,2S)-2-aminocyclopentanecarboxylic acid (cispentacin) and some other alicyclic β-amino acids have marked antifungal activity.…”

Section: -8mentioning

confidence: 99%

Mild and efficient ring opening of monoterpene-fused β-lactam enantiomers. Synthesis of novel β-amino acid derivatives

Szakonyi¹,

Fülöp²

2004

Arkivoc

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Section: -8mentioning

confidence: 99%

Mild and efficient ring opening of monoterpene-fused β-lactam enantiomers. Synthesis of novel β-amino acid derivatives

Szakonyi¹,

Fülöp²

2004

Arkivoc

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“…All members of GPCR superfamily, including OTR, consist of seven hydrophobic transmembranes-helices joined by alternating intra-and extracellular loops (Barberis et al, 1998). Since the work of Law and Vigneaud in 1960 (Law & Vigneaud, 1960) a large number of oxytocin analogs have been synthesized and many have been reported as oxytocin agonists or antagonists often more potent than the natural hormone (Toth et al, 1999). Nevertheless, no fully medical agents are available at present to treat woman in preterm labor.…”

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confidence: 99%

The influence of modification at position 2 on the side-chain conformation in oxytocin analogs.

Śmiech¹,

Kaźmierkiewicz²,

Lammek³

2006

Acta Biochim Pol

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The nonapeptide oxytocin (OT) is used in medicine to help begin and/or continue childbirth. Its analogs can be also used to control bleeding following fetus delivery. The main function of oxytocin is to stimulate contraction of uterus smooth muscle and the smooth muscle of mammary glands, thus regulating lactation. This paper describes theoretical simulations of the distribution of the torsional angles chi1 in the non-standard methylated phenylalanine residues of three oxytocin analogs: [(Phe)(2)o-Me]OT, [(Phe)(2)m-Me]OT, [(Phe)(2)p-Me]OT. The conformations of the oxytocin analogs were studied both in vacuum and in solution. We found some correlations between the biological activity of the considered peptides and the side-chain conformations of amino-acid residues 2 and 8.

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

et al. 2001

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SummaryWe report the solid-phase synthesis and receptor-binding properties of eleven oxytocin analogs (Mpa-XxxIle-Gln-Asn-Cys-Sar-Arg-Gly-NH2) containing non-coded amino acids in position 2: D-a-and L-ot-(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-fl-carboline-3-carboxylic acid and R-and S-1,2,3,4-tetrahydro-fl-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.Abbreviations: Symbols and abbreviations are in accordance with the recommendations of the IUPAC-IUB Joint Commission on Biochemical Nomenclature: Nomenclature and Symbolism for Amino Acids and Peptides [3]. The following other abbreviations were used: AcN,

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Synthesis of oxytocin antagonists containing conformationally constrained amino acids in position 2

Cited by 21 publications

References 23 publications

Mild and efficient ring opening of monoterpene-fused β-lactam enantiomers. Synthesis of novel β-amino acid derivatives

Mild and efficient ring opening of monoterpene-fused β-lactam enantiomers. Synthesis of novel β-amino acid derivatives

The influence of modification at position 2 on the side-chain conformation in oxytocin analogs.

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

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