Gene/Protein Disease Symptom Drug Enzyme Compound
Pivot Concepts:   Target Concepts:
Query: UNIPROT:P01178 (oxytocin)
 15,767 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

Five analogs of oxytocin have been synthesized with a homocysteine residue in position 6 and 2-, 3-, or 4-carbon residues in position 1. The compounds, which contain 20-, 21-, and 22-membered disulfide rings, respectively, were [1-alpha-mercaptoacetic acid,6-homocysteine]oxytocin, [6-homocysteine]oxytocin, [1-beta-mercaptopropionic acid,6-homocysteine]oxytocin, [1,6-homocystine]oxytocin, and [1-gamma-mercaptobutyric acid,6-homocysteine]oxytocin. The appropriate protected polypeptide intermediates were prepared by the solid-phase method of peptide synthesis. The protecting groups were removed by treatment with Na in NH3 and the disulfide bond was formed by oxidation with ICH2CH2I in aqueous MeOH. Purification was effected by partition chromatography followed by gel filtration. The pharmacological activities of all five analogs are reported for the oxytocic, avian vasodepressor, and rat pressor assays. Compared to oxytocin, these analogs exhibited sharply reduced agonist potencies, and several exhibited antagonist acitivty.
 ...
PMID:Synthesis and some pharmacological properties of five analogs of oxytocin having L-homocysteine in position 6. 124 4

[1-Alpha-Mercaptoacetic acid, 5-isoasparagine] oxytocin was synthesized to study the effects of moving the side chain carboxamide group of the amino acid residue in position 5 of oxytocin from the beta to the alpha position. The analog has an isoasparagine residue in position 5 and the 20-membered ring size of oxytocin is maintained by substituting cysteine in position 1 of oxytocin by alpha-mercaptoacetic acid. The analog was found to possess 0.098 +/- 0.002 U/mg of uterotonic activity but no milk-ejecting, antidiuretic or rat pressor activity could be detected. The substance did not inhibit the uterotonic or milk-ejecting activity induced by oxytocin nor the antidiuretic or rat pressor responses to the USP posterior pituitary standard. These results, together with the data available in the literature, indicate that an analog of oxytocin lacking the asparagine residue in position 5 is neither an agonist nor an antagonist. The observations may mean that the asparagine residue is critically important for the interaction of oxytocin with its receptor.
 ...
PMID:Studies on the importance of the asparagine residue in oxytocin. Synthesis and some pharmacological properties of [1-alpha-mercaptoacetic acid, 5-isoasparagine] oxytocin. 698 66