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Synthesis and opioid activity of dermorphin tetrapeptides bearing D-methionine S-oxide at position 2.
- Source :
-
Journal of medicinal chemistry [J Med Chem] 1986 Jun; Vol. 29 (6), pp. 889-94. - Publication Year :
- 1986
-
Abstract
- Eight new dermorphin tetrapeptides, X-Tyr-D-MetO-Phe-aa-Y (X = H, H2N = C(NH); aa = Gly, 2-aminoethanol, sarcosine; Y = NH2, NH-alkyl), were prepared and tested for opioid activity. They show dose-related naloxone-reversible opioid effects in vitro and in vivo. H-Tyr-D-MetO-Phe-Gly-NH2 (I) (guinea pig ileum IC50 = 13.6 nM; tail-flick ED50 = 1.97 pmol/mouse, icv, and 0.65 mumol/kg, sc), though less effective in the periphery, has central activities higher than those of dermorphin H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2. Following intracerebroventricular or subcutaneous administrations in mice, I is about respectively 1500 and 17 times as potent an analgesic as morphine.
- Subjects :
- Analgesics, Opioid pharmacology
Animals
Dose-Response Relationship, Drug
Guinea Pigs
Ileum drug effects
In Vitro Techniques
Methionine
Muscle Contraction drug effects
Oligopeptides pharmacology
Opioid Peptides
Structure-Activity Relationship
Analgesics, Opioid chemical synthesis
Oligopeptides chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 0022-2623
- Volume :
- 29
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Journal of medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 2872334
- Full Text :
- https://doi.org/10.1021/jm00156a003