The synthesis and opioid receptor binding affinities of analogues of dermorphin and its N-terminal tetrapeptide fragment with dibasic acids in position 2

Aleksandra Misicka, Andrzej W. Lipkowski, Jirina Slaninova, Peg Davis, Henry I. Yamamura, Frank Porreca, Victor J Hruby

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Analysis of possible μ opioid receptor active conformations for dermorphin suggested that the topographical location of the tyramine moiety of the N-tenninal tyrosine can be simulated with the phenol of tyrosine1 or desamino-tyrosine1 (4-hydroxyphenylpropionic acid) and a basic group located on the side chain of a dibasic acid residue located in position 2. The biological properties of respective analogs with D- or L-arginine, and D- or L-lysine in the position 2 of dermorphin or desaminodermorphin and their N-terminal tetrapeptide fragments, has provided evidence in support of this prediction, and questions the dogma that an N-terminal tyrosine is a necessary element for opioid agonist peptides.

Original languageEnglish (US)
Pages (from-to)1633-1640
Number of pages8
JournalLife Sciences
Volume57
Issue number18
DOIs
StatePublished - Sep 22 1995

Fingerprint

Opioid Receptors
Tyrosine
Tyramine
Acids
Opioid Peptides
Phenol
Opioid Analgesics
Lysine
Arginine
Conformations
Peptides
dermorphin
phloretic acid

Keywords

  • binding assays
  • dermorphin analogues
  • dibasic amino acids
  • GPI assay
  • MVD assay
  • δ opioid receptor
  • μ opioid receptor

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Pharmacology

Cite this

The synthesis and opioid receptor binding affinities of analogues of dermorphin and its N-terminal tetrapeptide fragment with dibasic acids in position 2. / Misicka, Aleksandra; Lipkowski, Andrzej W.; Slaninova, Jirina; Davis, Peg; Yamamura, Henry I.; Porreca, Frank; Hruby, Victor J.

In: Life Sciences, Vol. 57, No. 18, 22.09.1995, p. 1633-1640.

Research output: Contribution to journalArticle

Misicka, Aleksandra ; Lipkowski, Andrzej W. ; Slaninova, Jirina ; Davis, Peg ; Yamamura, Henry I. ; Porreca, Frank ; Hruby, Victor J. / The synthesis and opioid receptor binding affinities of analogues of dermorphin and its N-terminal tetrapeptide fragment with dibasic acids in position 2. In: Life Sciences. 1995 ; Vol. 57, No. 18. pp. 1633-1640.
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AU - Porreca, Frank

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