Open AccessChiral Effect of a Phe Residue in Position 3 of the Dmt1-l (or d )-Tic2 Analogues on Opioid Functional Activities
Author(s) -
Yeon Sun Lee,
Hong Qu,
Peg Davis,
Shou-Wu Ma,
Ruben Vardanyan,
Josephine Lai,
Frank Porreca,
Victor J. Hruby
Publication year - 2013
Publication title -
acs medicinal chemistry letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.065
H-Index - 66
ISSN - 1948-5875
DOI - 10.1021/ml400115n
Subject(s) - moiety , stereochemistry , residue (chemistry) , chemistry , opioid , opioid receptor , chirality (physics) , receptor , amino acid residue , amino acid , opioid peptide , biochemistry , peptide sequence , chiral symmetry , physics , nambu–jona lasinio model , quantum mechanics , gene , quark
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.