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Chiral Effect of a Phe Residue in Position 3 of the Dmt¹-L(or D)-Tic² Analogues on Opioid Functional Activities.

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.

SUBMITTER: Lee YS

PROVIDER: S-EPMC3956057 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Chiral Effect of a Phe Residue in Position 3 of the Dmt1-L(or D)-Tic2 Analogues on Opioid Functional Activities.

Lee Yeon Sun YS Qu Hong Chang HC Davis Peg P Ma Shou-Wu SW Vardanyan Ruben R Lai Josephine J Porreca Frank F Hruby Victor J VJ

ACS medicinal chemistry letters 20130701 7

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 th ...[more]

PMID: 24648867

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[Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1.

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In Vitro Membrane Permeation Studies and in Vivo Antinociception of Glycosylated Dmt1-DALDA Analogues.

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