Literature DB >> 17329100

Understanding the structural requirements of 4-anilidopiperidine analogues for biological activities at mu and delta opioid receptors.

Yeon Sun Lee1, Joel Nyberg, Sharif Moye, Richard S Agnes, Peg Davis, Shou-wu Ma, Josephine Lai, Frank Porreca, Ruben Vardanyan, Victor J Hruby.   

Abstract

New 4-anilidopiperidine analogues in which the phenethyl group of fentanyl was replaced by several aromatic ring-contained amino acids (or acids) were synthesized to study the biological effect of the substituents on mu and delta opioid receptor interactions. These analogues showed broad (47 nM-76 microM) but selective (up to 17-fold) binding affinities at the mu opioid receptor over the delta opioid receptor, as predicted from the message-address concept.

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Year:  2007        PMID： 17329100      PMCID： PMC2274923          DOI： 10.1016/j.bmcl.2007.01.114

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  11 in total

1.  A review of the chemical features associated with strong morphine-like activity.

Authors:  P A JANSSEN
Journal:  Br J Anaesth       Date:  1962-04       Impact factor: 9.166

2.  Design and synthesis of novel hydrazide-linked bifunctional peptides as delta/mu opioid receptor agonists and CCK-1/CCK-2 receptor antagonists.

Authors:  Yeon Sun Lee; Richard S Agnes; Hamid Badghisi; Peg Davis; Shou-wu Ma; Josephine Lai; Frank Porreca; Victor J Hruby
Journal:  J Med Chem       Date:  2006-03-09       Impact factor: 7.446

3.  Structure-activity studies of fentanyl.

Authors:  A F Casy; M R Huckstep
Journal:  J Pharm Pharmacol       Date:  1988-09       Impact factor: 3.765

Review 4.  Recent developments in the design of receptor specific opioid peptides.

Authors:  V J Hruby; C A Gehrig
Journal:  Med Res Rev       Date:  1989 Jul-Sep       Impact factor: 12.944

5.  Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor.

Authors:  G Subramanian; M G Paterlini; P S Portoghese; D M Ferguson
Journal:  J Med Chem       Date:  2000-02-10       Impact factor: 7.446

6.  Long-acting fentanyl analogues: synthesis and pharmacology of N-(1-phenylpyrazolyl)-N-(1-phenylalkyl-4-piperidyl)propanamides.

Authors:  Nadine Jagerovic; Carolina Cano; José Elguero; Pilar Goya; Luis F Callado; J Javier Meana; Rocío Girón; Raquel Abalo; David Ruiz; Carlos Goicoechea; M A Isabel Martín
Journal:  Bioorg Med Chem       Date:  2002-03       Impact factor: 3.641

7.  Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.

Authors:  P S Portoghese; M Sultana; A E Takemori
Journal:  J Med Chem       Date:  1990-06       Impact factor: 7.446

8.  Characterization of opiates, neuroleptics, and synthetic analogs at ORL1 and opioid receptors.

Authors:  N Zaveri; W E Polgar; C M Olsen; A B Kelson; P Grundt; J W Lewis; L Toll
Journal:  Eur J Pharmacol       Date:  2001-09-28       Impact factor: 4.432

9.  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

Review 10.  Dmt and opioid peptides: a potent alliance.

Authors:  Sharon D Bryant; Yunden Jinsmaa; Severo Salvadori; Yoshio Okada; Lawrence H Lazarus
Journal:  Biopolymers       Date:  2003       Impact factor: 2.505
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  13 in total

Review 1.  Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications.

Authors:  Ruben S Vardanyan; Victor J Hruby
Journal:  Future Med Chem       Date:  2014-03       Impact factor: 3.808

2.  Discovery of 5-substituted tetrahydronaphthalen-2yl-methyl with N-phenyl-N-(piperidin-4-yl)propionamide derivatives as potent opioid receptor ligands.

Authors:  Srinivas Deekonda; Lauren Wugalter; Vinod Kulkarni; David Rankin; Tally M Largent-Milnes; Peg Davis; Neemah M Bassirirad; Josephine Lai; Todd W Vanderah; Frank Porreca; Victor J Hruby
Journal:  Bioorg Med Chem       Date:  2015-08-04       Impact factor: 3.641

3.  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
Journal:  J Med Chem       Date:  2010-12-03       Impact factor: 7.446

4.  Synthesis and Investigation of Mixed μ-Opioid and δ-Opioid Agonists as Possible Bivalent Ligands for Treatment of Pain.

Authors:  Ruben S Vardanyan; James P Cain; Saghar Mowlazadeh Haghighi; Vlad K Kumirov; Mary I McIntosh; Alexander J Sandweiss; Frank Porreca; Victor J Hruby
Journal:  J Heterocycl Chem       Date:  2016-06-01       Impact factor: 2.193

5.  Proton sharing and transfer in some zwitterionic compounds based on 4-oxo-4-((1-phenethylpiperidin-4-yl)(phenyl)amino)alcanoic acids.

Authors:  Gary S Nichol; Vlad K Kumirov; Ruben Vardanyan; Victor J Hruby
Journal:  CrystEngComm       Date:  2010       Impact factor: 3.545

6.  Enkephalin analogues with N-phenyl-N-(piperidin-2-ylmethyl)propionamide derivatives: Synthesis and biological evaluations.

Authors:  Srinivas Deekonda; Jacob Cole; Sydney Sunna; David Rankin; Tally M Largent-Milnes; Peg Davis; Neemah M BassiriRad; Josephine Lai; Todd W Vanderah; Frank Porecca; Victor J Hruby
Journal:  Bioorg Med Chem Lett       Date:  2015-11-03       Impact factor: 2.823

7.  Development of novel enkephalin analogues that have enhanced opioid activities at both mu and delta opioid receptors.

Authors:  Yeon Sun Lee; Ravil Petrov; Chad K Park; Shou-wu Ma; Peg Davis; Josephine Lai; Frank Porreca; Ruben Vardanyan; Victor J Hruby
Journal:  J Med Chem       Date:  2007-10-10       Impact factor: 7.446

8.  Development of mu/delta opioid ligands: enkephalin analogues containing 4-anilidopiperidine moiety.

Authors:  YeonSun Lee; Ravil Petrov; Vinod Kulkarni; Byoung J Min; Shou-Wu Ma; Peg Davis; Janice Oyarzo; Todd Vanderah; Josephine Lai; Frank Porreca; Ruben Vardanyan; Victor J Hruby
Journal:  Adv Exp Med Biol       Date:  2009       Impact factor: 2.622

9.  Further studies on lead compounds containing the opioid pharmacophore Dmt-Tic.

Authors:  Gianfranco Balboni; Stella Fiorini; Anna Baldisserotto; Claudio Trapella; Yusuke Sasaki; Akihiro Ambo; Ewa D Marczak; Lawrence H Lazarus; Severo Salvadori
Journal:  J Med Chem       Date:  2008-08-05       Impact factor: 7.446

10.  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
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