Synthesis and biological activities of position one and three transposed analogs of the opioid peptide YKFA

John E. Burden, Peg Davis, Frank Porreca, Arno F. Spatola

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)3441-3446
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume9
Issue number24
StatePublished - Dec 20 1999

Fingerprint

delta Opioid Receptor
Opioid Peptides
mu Opioid Receptor
Bioactivity
Somatostatin
Hydroxyl Radical
Opioid Analgesics
tyrosyl-cyclo(lysyl-phenylalanyl-alanyl)

Keywords

  • Agonists
  • Analgesics
  • Peptides and polypeptides
  • Receptors

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Synthesis and biological activities of position one and three transposed analogs of the opioid peptide YKFA. / Burden, John E.; Davis, Peg; Porreca, Frank; Spatola, Arno F.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 9, No. 24, 20.12.1999, p. 3441-3446.

Research output: Contribution to journalArticle

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