Synthesis and biological activities of position one and three transposed analogs of the opioid peptide YKFA.
Tyr-c[D-Lys-Phe-Ala], YKFA, is a potent opioid peptide analog with subnanomolar IC50s toward mu and delta receptors. Transposing Phe and Tyr, a modification found to promote mu antagonist activity in opioid/somatostatin hybrids, gave surprisingly high mu agonist activities for several related analogs, considering the lack of a 1-position hydroxyl function.
Burden
J E
JE
Department of Chemistry, University of Louisville, KY 40292 USA.
Davis
P
P
Porreca
F
F
Spatola
A F
AF
D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D013058:Mass Spectrometry; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017450:Receptors, Opioid, mu / Q000037:antagonists & inhibitors*
D009842:Oligopeptides; D010456:Peptides, Cyclic; D017450:Receptors, Opioid, mu; C403249:tyrosyl-cyclo(lysyl-phenylalanyl-alanyl)