Literature DB >> 24648867

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

Yeon Sun Lee1, Hong Chang Qu1, Peg Davis2, Shou-Wu Ma2, Ruben Vardanyan1, Josephine Lai2, Frank Porreca2, Victor J Hruby1.   

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.

Entities:  

Keywords:  Dmt-Tic; chirality; opioid functional activities; structure–activity relationship; δ opioid receptor

Year:  2013        PMID： 24648867      PMCID： PMC3956057          DOI： 10.1021/ml400115n

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  16 in total

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Journal:  J Med Chem       Date:  2002-10-10       Impact factor: 7.446

2.  Evaluation of the Dmt-Tic pharmacophore: conversion of a potent delta-opioid receptor antagonist into a potent delta agonist and ligands with mixed properties.

Authors:  Gianfranco Balboni; Remo Guerrini; Severo Salvadori; Clementina Bianchi; Daniela Rizzi; Sharon D Bryant; Lawrence H Lazarus
Journal:  J Med Chem       Date:  2002-01-31       Impact factor: 7.446

Review 3.  New delta-opioid antagonists as pharmacological probes.

Authors:  S D Bryant; S Salvadori; P S Cooper; L H Lazarus
Journal:  Trends Pharmacol Sci       Date:  1998-02       Impact factor: 14.819

4.  Extended TIP(P) analogues as precursors for labeled delta-opioid receptor ligands.

Authors:  V Kumar; T F Murray; J V Aldrich
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5.  Development of potent μ and δ opioid agonists with high lipophilicity.

Authors:  Yeon Sun Lee; Vinod Kulkarani; Scott M Cowell; Shou-wu Ma; Peg Davis; Katherine E Hanlon; Todd W Vanderah; Josephine Lai; Frank Porreca; Ruben Vardanyan; Victor J Hruby
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6.  The opioid mu agonist/delta antagonist DIPP-NH(2)[Psi] produces a potent analgesic effect, no physical dependence, and less tolerance than morphine in rats.

Authors:  P W Schiller; M E Fundytus; L Merovitz; G Weltrowska; T M Nguyen; C Lemieux; N N Chung; T J Coderre
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7.  Delta opioidmimetic antagonists: prototypes for designing a new generation of ultraselective opioid peptides.

Authors:  S Salvadori; M Attila; G Balboni; C Bianchi; S D Bryant; O Crescenzi; R Guerrini; D Picone; T Tancredi; P A Temussi
Journal:  Mol Med       Date:  1995-09       Impact factor: 6.354

8.  Influence of the side chain next to C-terminal benzimidazole in opioid pseudopeptides containing the Dmt-Tic pharmacophore.

Authors:  Gianfranco Balboni; Claudio Trapella; Yusuke Sasaki; Akihiro Ambo; Ewa D Marczak; Lawrence H Lazarus; Severo Salvadori
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9.  Opioid and melanocortin receptors: do they have overlapping pharmacophores?

Authors:  Yeon Sun Lee; Richard S Agnes; James P Cain; Vinod Kulkarni; Minying Cai; Christine Salibay; Kathy Ciano; Ravil Petrov; Alexander Mayorov; Josef Vagner; Dev Trivedi; Peg Davis; Shou-wu Ma; Josephine Lai; Frank Porreca; Ruben Vardanyan; Victor J Hruby
Journal:  Biopolymers       Date:  2008       Impact factor: 2.505

10.  Conversion of enkephalin and dermorphin into delta-selective opioid antagonists by single-residue substitution.

Authors:  T Tancredi; S Salvadori; P Amodeo; D Picone; L H Lazarus; S D Bryant; R Guerrini; G Marzola; P A Temussi
Journal:  Eur J Biochem       Date:  1994-08-15
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  2 in total

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Review 2.  Peptidomimetics and Their Applications for Opioid Peptide Drug Discovery.

Authors:  Yeon Sun Lee
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