Chiral effect of a Phe residue in position 3 of the Dmt1-l (or d)-Tic2 analogues on opioid functional activities

Yeon Sun Lee, Hongchang Qu, Peg Davis, Shou Wu Ma, Ruben S Vardanyan, Josephine Lai, Frank Porreca, Victor J Hruby

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

In this letter, we describe a structure-activity relationships study, specifically related to the chirality of third amino acid residue in our H-Dmt-l(or d)-Tic analogues, of which C-terminus is attached to a piperidinyl moiety. Observed selectivities and functional activities of these analogues demonstrated that the chiralities of the second and third position residues are crucial for determining whether these ligands act as antagonists or agonists at the δ opioid receptor, but not at the μ opioid receptor.

Original languageEnglish (US)
Pages (from-to)656-659
Number of pages4
JournalACS Medicinal Chemistry Letters
Volume4
Issue number7
DOIs
StatePublished - Jul 11 2013

Fingerprint

Chirality
Opioid Receptors
Opioid Analgesics
Structure-Activity Relationship
Ligands
Amino Acids
2',6'-dimethyltyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Keywords

  • δ opioid receptor
  • chirality
  • Dmt-Tic
  • opioid functional activities
  • structure-activity relationship

ASJC Scopus subject areas

  • Organic Chemistry
  • Drug Discovery
  • Biochemistry

Cite this

Chiral effect of a Phe residue in position 3 of the Dmt1-l (or d)-Tic2 analogues on opioid functional activities. / Lee, Yeon Sun; Qu, Hongchang; Davis, Peg; Ma, Shou Wu; Vardanyan, Ruben S; Lai, Josephine; Porreca, Frank; Hruby, Victor J.

In: ACS Medicinal Chemistry Letters, Vol. 4, No. 7, 11.07.2013, p. 656-659.

Research output: Contribution to journalArticle

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AU - Vardanyan, Ruben S

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AU - Porreca, Frank

AU - Hruby, Victor J

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