Probing opioid receptor interactions with azacycloalkane amino acids. Synthesis of a potent and selective ORL1 antagonist

Liliane Halab, Jérôme A J Becker, Z. Darula, Dirk Tourwé, Brigitte L. Kieffer, Frédéric Simonin, William D. Lubell

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

Azacycloalkane turn mimics 6-9 were used to explore the relationship between conformation and biological activity of peptide ligands to the opioid receptor-like (ORL1) receptor. Three azabicyclo[x.y.0]alkane amino acids and a 5-tBuPro type VI β-turn mimic were introduced into peptides 10-13 by solid-phase synthesis on MBHA resin. Biological examination of peptides 10-13 showed two new antagonists (10 and 12) exhibiting increased selectivity for the ORL1 receptor.

Original languageEnglish
Pages (from-to)5353-5357
Number of pages5
JournalJournal of Medicinal Chemistry
Volume45
Issue number24
DOIs
Publication statusPublished - Nov 21 2002

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Opioid Receptors
Amino Acids
Peptides
Solid-Phase Synthesis Techniques
Alkanes
Bioactivity
Conformations
Ligands
nociceptin receptor

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Probing opioid receptor interactions with azacycloalkane amino acids. Synthesis of a potent and selective ORL1 antagonist. / Halab, Liliane; Becker, Jérôme A J; Darula, Z.; Tourwé, Dirk; Kieffer, Brigitte L.; Simonin, Frédéric; Lubell, William D.

In: Journal of Medicinal Chemistry, Vol. 45, No. 24, 21.11.2002, p. 5353-5357.

Research output: Contribution to journalArticle

Halab, Liliane ; Becker, Jérôme A J ; Darula, Z. ; Tourwé, Dirk ; Kieffer, Brigitte L. ; Simonin, Frédéric ; Lubell, William D. / Probing opioid receptor interactions with azacycloalkane amino acids. Synthesis of a potent and selective ORL1 antagonist. In: Journal of Medicinal Chemistry. 2002 ; Vol. 45, No. 24. pp. 5353-5357.
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