International journal of peptide & protein research · 1985 · 22 citations · 12 references
MedicineMedicinal ChemistryPharmacologyMolecular PharmacologyNeuropharmacologyPain MedicineAnalgesic PharmacologyNeuropeptide PharmacologyOpioid AnalgesicsOpioid PharmacologyPeptide Bond ChemistryPeptide ChemistryBiological Assay PotencyEndogenous OpioidsOpioid Peptide PharmacologyOpioid PharmacodynamicsPeptide Analogue DesignPeptide Medicinal ChemistrySubcutaneous Drug AdministrationSynthetic Opioids
We studied the effect of partial retro-inverso modification of selected peptide bonds of dermorphin (H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2. The modifications concern two consecutive peptide bonds (Phe3-Cly4-Tyr5, I) or a single one (Gly4-Tyr5-, II or Phe3-Gly4, III). All pseudoheptapeptides showed low opioid activity in the in vitro and in vivo tests. Compound III has a biological potency comparable to that of morphine but only 2-5% of original dermorphin when tested in guinea pig ileum preparation and in mice tail-flick assay after intracerebro or subcutaneous administration.
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