Literature DB >> 19560919

Synthesis and evaluation of new endomorphin analogues modified at the Pro(2) residue.

Domenica Torino1, Adriano Mollica, Francesco Pinnen, Gino Lucente, Federica Feliciani, Peg Davis, Josephine Lai, Shou-Wu Ma, Frank Porreca, Victor J Hruby.   

Abstract

Six new endomorphin analogues, incorporating constrained amino acids in place of native proline have been synthesized. Residues of (S)-azetidine-2-carboxylic acid (Aze), 3,4-dehydro-(S)-proline (Delta(3)Pro), azetidine-3-carboxylic acid (3Aze) and dehydro-alanine (DeltaAla) have been used to prepare [Delta(3)Pro(2)]EM-2 (1), [Aze(2)]EM-1 (2), [Aze(2)]EM-2 (3), [3Aze(2)]EM-1 (4), [3Aze(2)]EM-2 (5) and [DeltaAla(2)]EM-2 (6). Binding assays and functional bioactivities for mu- and delta-receptors are reported. The highest affinity, bioactivity and selectivity are shown by peptides 2 and 3 containing the Aze residue.

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Year:  2009        PMID： 19560919      PMCID： PMC2737817          DOI： 10.1016/j.bmcl.2009.06.008

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


  35 in total

Review 1.  Endomorphin-1 and endomorphin-2: pharmacology of the selective endogenous mu-opioid receptor agonists.

Authors:  G Horvath
Journal:  Pharmacol Ther       Date:  2000-12       Impact factor: 12.310

2.  Dissociation of analgesic and rewarding effects of endomorphin-1 in rats.

Authors:  A M Wilson; R D Soignier; J E Zadina; A J Kastin; W L Nores; R D Olson; G A Olson
Journal:  Peptides       Date:  2000-12       Impact factor: 3.750

3.  Endomorphin-1 analogues containing beta-proline are mu-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance.

Authors:  Giuliana Cardillo; Luca Gentilucci; Ahmed R Qasem; Fabio Sgarzi; Santi Spampinato
Journal:  J Med Chem       Date:  2002-06-06       Impact factor: 7.446

4.  Synthesis and binding activity of endomorphin-1 analogues containing beta-amino acids.

Authors:  G Cardillo; L Gentilucci; P Melchiorre; S Spampinato
Journal:  Bioorg Med Chem Lett       Date:  2000-12-18       Impact factor: 2.823

5.  Pronociceptive actions of dynorphin maintain chronic neuropathic pain.

Authors:  Z Wang; L R Gardell; M H Ossipov; T W Vanderah; M B Brennan; U Hochgeschwender; V J Hruby; T P Malan; J Lai; F Porreca
Journal:  J Neurosci       Date:  2001-03-01       Impact factor: 6.167

6.  Differential cardiorespiratory effects of endomorphin 1, endomorphin 2, DAMGO, and morphine.

Authors:  M A Czapla; D Gozal; O A Alea; R C Beckerman; J E Zadina
Journal:  Am J Respir Crit Care Med       Date:  2000-09       Impact factor: 21.405

7.  Synthesis of stereoisomeric analogues of endomorphin-2, H-Tyr-Pro-Phe-Phe-NH(2), and examination of their opioid receptor binding activities and solution conformation.

Authors:  Y Okada; A Fukumizu; M Takahashi; Y Shimizu; Y Tsuda; T Yokoi; S D Bryant; L H Lazarus
Journal:  Biochem Biophys Res Commun       Date:  2000-09-16       Impact factor: 3.575

8.  Synthesis and biological activity of endomorphin-2 analogs incorporating piperidine-2-, 3- or 4-carboxylic acids instead of proline in position 2.

Authors:  Renata Staniszewska; Jakub Fichna; Katarzyna Gach; Geza Toth; Jeroen Poels; Jozef Vanden Broeck; Anna Janecka
Journal:  Chem Biol Drug Des       Date:  2008-06-13       Impact factor: 2.817

9.  New endomorphin analogues containing alicyclic beta-amino acids: influence on bioactive conformation and pharmacological profile.

Authors:  Attila Keresztes; Mária Szucs; Attila Borics; Katalin E Kövér; Eniko Forró; Ferenc Fülöp; Csaba Tömböly; Antal Péter; Annamária Páhi; Gabriella Fábián; Mariann Murányi; Géza Tóth
Journal:  J Med Chem       Date:  2008-06-24       Impact factor: 7.446

10.  Discovery of further pyrrolidine trans-lactams as inhibitors of human neutrophil elastase (HNE) with potential as development candidates and the crystal structure of HNE complexed with an inhibitor (GW475151).

Authors:  Simon J F Macdonald; Michael D Dowle; Lee A Harrison; Geoffrey D E Clarke; Graham G A Inglis; Martin R Johnson; Pritom Shah; Robin A Smith; Augustin Amour; Gill Fleetwood; Davina C Humphreys; Christopher R Molloy; Mary Dixon; Rosalind E Godward; Alan J Wonacott; Onkar M P Singh; Simon T Hodgson; George W Hardy
Journal:  J Med Chem       Date:  2002-08-29       Impact factor: 7.446
View more
  7 in total

1.  Synthesis and evaluation of new endomorphin-2 analogues containing (Z)-alpha,beta-didehydrophenylalanine (Delta(Z)Phe) residues.

Authors:  Domenica Torino; Adriano Mollica; Francesco Pinnen; Federica Feliciani; Gino Lucente; Giancarlo Fabrizi; Gustavo Portalone; Peg Davis; Josephine Lai; Shou-Wu Ma; Frank Porreca; Victor J Hruby
Journal:  J Med Chem       Date:  2010-06-10       Impact factor: 7.446

2.  The cis-4-amino-L-proline residue as a scaffold for the synthesis of cyclic and linear endomorphin-2 analogues.

Authors:  Adriano Mollica; Francesco Pinnen; Azzurra Stefanucci; Federica Feliciani; Cristina Campestre; Luisa Mannina; Anatoly P Sobolev; Gino Lucente; Peg Davis; Josephine Lai; Shou-Wu Ma; Frank Porreca; Victor J Hruby
Journal:  J Med Chem       Date:  2012-03-22       Impact factor: 7.446

3.  Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2.

Authors:  Cesare Giordano; Anna Sansone; Annalisa Masi; Gino Lucente; Pasqualina Punzi; Adriano Mollica; Francesco Pinnen; Federica Feliciani; Ivana Cacciatore; Peg Davis; Josephine Lai; Shou-Wu Ma; Frank Porreca; Victor Hruby
Journal:  Eur J Med Chem       Date:  2010-07-21       Impact factor: 6.514

Review 4.  Synthesis and bioactivity of secondary metabolites from marine sponges containing dibrominated indolic systems.

Authors:  Adriano Mollica; Marcello Locatelli; Azzurra Stefanucci; Francesco Pinnen
Journal:  Molecules       Date:  2012-05-21       Impact factor: 4.411

Review 5.  Food-Derived Opioid Peptides in Human Health: A Review.

Authors:  Akanksha Tyagi; Eric Banan-Mwine Daliri; Fred Kwami Ofosu; Su-Jung Yeon; Deog-Hwan Oh
Journal:  Int J Mol Sci       Date:  2020-11-21       Impact factor: 5.923

6.  Synthesis, Pharmacological Evaluation, and Computational Studies of Cyclic Opioid Peptidomimetics Containing β3-Lysine.

Authors:  Karol Wtorek; Piotr F J Lipiński; Anna Adamska-Bartłomiejczyk; Justyna Piekielna-Ciesielska; Jarosław Sukiennik; Alicja Kluczyk; Anna Janecka
Journal:  Molecules       Date:  2021-12-28       Impact factor: 4.411

Review 7.  Peptidomimetics and Their Applications for Opioid Peptide Drug Discovery.

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

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