Literature DB >> 16942040

New opioid designed multiple ligand from Dmt-Tic and morphinan pharmacophores.

John L Neumeyer1, Xuemei Peng, Brian I Knapp, Jean M Bidlack, Lawrence H Lazarus, Severo Salvadori, Claudio Trapella, Gianfranco Balboni.   

Abstract

Here, we report the synthesis of a designed multi-pharmacophore ligand derived from the linkage of a delta selective peptide antagonist (Dmt-Tic) and a mu/kappa morphinan agonist butorphan (MCL 101) through a two methylene spacer. The new compound MCL 450 maintains the same characteristics as those the two reference compounds. MCL 450 represents a useful starting point for the synthesis of other multiple opioid ligands endowed with analgesic properties with low tolerance and dependence.

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Year:  2006        PMID： 16942040      PMCID： PMC2435260          DOI： 10.1021/jm0605785

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  21 in total

1.  Oligomerization of mu- and delta-opioid receptors. Generation of novel functional properties.

Authors:  S R George; T Fan; Z Xie; R Tse; V Tam; G Varghese; B F O'Dowd
Journal:  J Biol Chem       Date:  2000-08-25       Impact factor: 5.157

2.  From models to molecules: opioid receptor dimers, bivalent ligands, and selective opioid receptor probes.

Authors:  P S Portoghese
Journal:  J Med Chem       Date:  2001-07-05       Impact factor: 7.446

Review 3.  From magic bullets to designed multiple ligands.

Authors:  Richard Morphy; Corinne Kay; Zoran Rankovic
Journal:  Drug Discov Today       Date:  2004-08-01       Impact factor: 7.851

4.  Direct influence of C-terminally substituted amino acids in the Dmt-Tic pharmacophore on delta-opioid receptor selectivity and antagonism.

Authors:  Gianfranco Balboni; Severo Salvadori; Remo Guerrini; Lucia Negri; Elisa Giannini; Sharon D Bryant; Yunden Jinsmaa; Lawrence H Lazarus
Journal:  J Med Chem       Date:  2004-07-29       Impact factor: 7.446

5.  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

6.  6-N,N-dimethylamino-2,3-naphthalimide: a new environment-sensitive fluorescent probe in delta- and mu-selective opioid peptides.

Authors:  M Eugenio Vázquez; Juan B Blanco; Severo Salvadori; Claudio Trapella; Roberto Argazzi; Sharon D Bryant; Yunden Jinsmaa; Lawrence H Lazarus; Lucia Negri; Elisa Giannini; Roberta Lattanzi; Mariantonella Colucci; Gianfranco Balboni
Journal:  J Med Chem       Date:  2006-06-15       Impact factor: 7.446

7.  Further studies on the Dmt-Tic pharmacophore: hydrophobic substituents at the C-terminus endow delta antagonists to manifest mu agonism or mu antagonism.

Authors:  S Salvadori; R Guerrini; G Balboni; C Bianchi; S D Bryant; P S Cooper; L H Lazarus
Journal:  J Med Chem       Date:  1999-12-02       Impact factor: 7.446

Review 8.  Opioids and their complicated receptor complexes.

Authors:  B A Jordan; S Cvejic; L A Devi
Journal:  Neuropsychopharmacology       Date:  2000-10       Impact factor: 7.853

9.  Synthesis and antinociceptive activity of orally active opioid peptides: improvement of oral bioavailability by esterification.

Authors:  Tadashi Ogawa; Mamoru Araki; Tetsuhisa Miyamae; Toru Okayama; Masaki Hagiwara; Shinobu Sakurada; Tadanori Morikawa
Journal:  Chem Pharm Bull (Tokyo)       Date:  2003-07       Impact factor: 1.645

10.  Only one pharmacophore is required for the kappa opioid antagonist selectivity of norbinaltorphimine.

Authors:  P S Portoghese; H Nagase; A E Takemori
Journal:  J Med Chem       Date:  1988-07       Impact factor: 7.446
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  12 in total

1.  Dual targeting of histone deacetylase and topoisomerase II with novel bifunctional inhibitors.

Authors:  William Guerrant; Vishal Patil; Joshua C Canzoneri; Adegboyega K Oyelere
Journal:  J Med Chem       Date:  2012-02-13       Impact factor: 7.446

2.  Pharmacological properties of bivalent ligands containing butorphan linked to nalbuphine, naltrexone, and naloxone at mu, delta, and kappa opioid receptors.

Authors:  Xuemei Peng; Brian I Knapp; Jean M Bidlack; John L Neumeyer
Journal:  J Med Chem       Date:  2007-04-04       Impact factor: 7.446

Review 3.  Endogenous opiates and behavior: 2006.

Authors:  Richard J Bodnar
Journal:  Peptides       Date:  2007-09-11       Impact factor: 3.750

4.  A new opioid designed multiple ligand derived from the micro opioid agonist endomorphin-2 and the delta opioid antagonist pharmacophore Dmt-Tic.

Authors:  Severo Salvadori; Claudio Trapella; Stella Fiorini; Lucia Negri; Roberta Lattanzi; Sharon D Bryant; Yunden Jinsmaa; Lawrence H Lazarus; Gianfranco Balboni
Journal:  Bioorg Med Chem       Date:  2007-08-29       Impact factor: 3.641

Review 5.  Opioid-receptor-heteromer-specific trafficking and pharmacology.

Authors:  Richard M van Rijn; Jennifer L Whistler; Maria Waldhoer
Journal:  Curr Opin Pharmacol       Date:  2009-10-19       Impact factor: 5.547

6.  Synthesis and binding affinity of novel mono- and bivalent morphinan ligands for κ, μ, and δ opioid receptors.

Authors:  Bin Zhang; Tangzhi Zhang; Anna W Sromek; Thomas Scrimale; Jean M Bidlack; John L Neumeyer
Journal:  Bioorg Med Chem       Date:  2011-03-26       Impact factor: 3.641

7.  Synthesis and biological evaluation of bivalent ligands for the cannabinoid 1 receptor.

Authors:  Yanan Zhang; Anne Gilliam; Rangan Maitra; M Imad Damaj; Julianne M Tajuba; Herbert H Seltzman; Brian F Thomas
Journal:  J Med Chem       Date:  2010-10-14       Impact factor: 7.446

8.  Opioid bifunctional ligands from morphine and the opioid pharmacophore Dmt-Tic.

Authors:  Gianfranco Balboni; Severo Salvadori; Ewa D Marczak; Brian I Knapp; Jean M Bidlack; Lawrence H Lazarus; Xuemei Peng; Yu Gui Si; John L Neumeyer
Journal:  Eur J Med Chem       Date:  2010-12-08       Impact factor: 6.514

9.  Further studies on the effect of lysine at the C-terminus of the Dmt-Tic opioid pharmacophore.

Authors:  Gianfranco Balboni; Valentina Onnis; Cenzo Congiu; Margherita Zotti; Yusuke Sasaki; Akihiro Ambo; Sharon D Bryant; Yunden Jinsmaa; Lawrence H Lazarus; Ilaria Lazzari; Claudio Trapella; Severo Salvadori
Journal:  Bioorg Med Chem       Date:  2007-02-22       Impact factor: 3.641

Review 10.  Bi- or multifunctional opioid peptide drugs.

Authors:  Peter W Schiller
Journal:  Life Sci       Date:  2009-03-11       Impact factor: 5.037
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