Literature DB >> 20137938

Novel multiple opioid ligands based on 4-aminobenzazepinone (Aba), azepinoindole (Aia) and tetrahydroisoquinoline (Tic) scaffolds.

Steven Ballet1, Ewa D Marczak, Debby Feytens, Severo Salvadori, Yusuke Sasaki, Andrew D Abell, Lawrence H Lazarus, Gianfranco Balboni, Dirk Tourwé.   

Abstract

The dimerization and trimerization of the Dmt-Tic, Dmt-Aia and Dmt-Aba pharmacophores provided multiple ligands which were evaluated in vitro for opioid receptor binding and functional activity. Whereas the Tic- and Aba multimers proved to be dual and balanced delta/mu antagonists, as determined by the functional [S(35)]GTPgammaS binding assay, the dimerization of potent Aia-based 'parent' ligands unexpectedly resulted in substantial less efficient receptor binding and non-active dimeric compounds. Copyright 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 20137938      PMCID： PMC2840614          DOI： 10.1016/j.bmcl.2010.01.055

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


  35 in total

1.  Development and validation of opioid ligand-receptor interaction models: the structural basis of mu vs delta selectivity.

Authors:  H I Mosberg; C B Fowler
Journal:  J Pept Res       Date:  2002-12

2.  A chimeric opioid peptide with mixed mu agonist/delta antagonist properties.

Authors:  G Weltrowska; C Lemieux; N N Chung; P W Schiller
Journal:  J Pept Res       Date:  2004-02

3.  Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction.

Authors:  Y Cheng; W H Prusoff
Journal:  Biochem Pharmacol       Date:  1973-12-01       Impact factor: 5.858

4.  Double-enkephalins--synthesis, activity on guinea-pig ileum, and analgesic effect.

Authors:  A W Lipkowski; A M Konecka; I Sroczyńska
Journal:  Peptides       Date:  1982 Jul-Aug       Impact factor: 3.750

5.  Double enkephalins.

Authors:  A W Lipkowski; A M Konecka; B Sadowski
Journal:  Pol J Pharmacol Pharm       Date:  1982

Review 6.  The TIPP opioid peptide family: development of delta antagonists, delta agonists, and mixed mu agonist/delta antagonists.

Authors:  P W Schiller; G Weltrowska; I Berezowska; T M Nguyen; B C Wilkes; C Lemieux; N N Chung
Journal:  Biopolymers       Date:  1999       Impact factor: 2.505

7.  Receptor binding and biological activity of bivalent enkephalins.

Authors:  T Costa; M Wüster; A Herz; Y Shimohigashi; H C Chen; D Rodbard
Journal:  Biochem Pharmacol       Date:  1985-01-01       Impact factor: 5.858

8.  Kinetic parameters of narcotic agonists and antagonists, with particular reference to N-allylnoroxymorphone (naloxone).

Authors:  H W Kosterlitz; A J Watt
Journal:  Br J Pharmacol Chemother       Date:  1968-06

9.  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
Journal:  J Med Chem       Date:  2009-09-10       Impact factor: 7.446

10.  Oral bioavailability of a new class of micro-opioid receptor agonists containing 3,6-bis[Dmt-NH(CH(2))(n)]-2(1H)-pyrazinone with central-mediated analgesia.

Authors:  Yunden Jinsmaa; Anna Miyazaki; Yoshio Fujita; Tingyou Li; Yutaka Fujisawa; Kimitaka Shiotani; Yuko Tsuda; Toshio Yokoi; Akihiro Ambo; Yusuke Sasaki; Sharon D Bryant; Lawrence H Lazarus; Yoshio Okada
Journal:  J Med Chem       Date:  2004-05-06       Impact factor: 7.446
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  3 in total

1.  Design of novel neurokinin 1 receptor antagonists based on conformationally constrained aromatic amino acids and discovery of a potent chimeric opioid agonist-neurokinin 1 receptor antagonist.

Authors:  Steven Ballet; Debby Feytens; Koen Buysse; Nga N Chung; Carole Lemieux; Suneeta Tumati; Attila Keresztes; Joost Van Duppen; Josephine Lai; Eva Varga; Frank Porreca; Peter W Schiller; Jozef Vanden Broeck; Dirk Tourwé
Journal:  J Med Chem       Date:  2011-03-17       Impact factor: 7.446

2.  Dual Alleviation of Acute and Neuropathic Pain by Fused Opioid Agonist-Neurokinin 1 Antagonist Peptidomimetics.

Authors:  Cecilia Betti; Joanna Starnowska; Joanna Mika; Jolanta Dyniewicz; Lukasz Frankiewicz; Alexandre Novoa; Marta Bochynska; Attila Keresztes; Piotr Kosson; Wioletta Makuch; Joost Van Duppen; Nga N Chung; Jozef Vanden Broeck; Andrzej W Lipkowski; Peter W Schiller; Frans Janssens; Marc Ceusters; François Sommen; Theo Meert; Barbara Przewlocka; Dirk Tourwé; Steven Ballet
Journal:  ACS Med Chem Lett       Date:  2015-10-31       Impact factor: 4.345

Review 3.  Peptidomimetics and Their Applications for Opioid Peptide Drug Discovery.

Authors:  Yeon Sun Lee
Journal:  Biomolecules       Date:  2022-09-05
  3 in total

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