Literature DB >> 23547584

Biological active analogues of the opioid peptide biphalin: mixed α/β(3)-peptides.

Adriano Mollica1, Francesco Pinnen, Roberto Costante, Marcello Locatelli, Azzurra Stefanucci, Stefano Pieretti, Peg Davis, Josephine Lai, David Rankin, Frank Porreca, Victor J Hruby.   

Abstract

Natural residues of the dimeric opioid peptide Biphalin were replaced by the corresponding homo-β(3) amino acids. The derivative 1 containing hβ(3) Phe in place of Phe showed good μ- and δ-receptor affinities (Ki(δ) = 0.72 nM; Ki(μ) = 1.1 nM) and antinociceptive activity in vivo together with an increased enzymatic stability in human plasma.

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Year:  2013        PMID： 23547584      PMCID： PMC3942533          DOI： 10.1021/jm301456c

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


  30 in total

1.  The opioid peptide analogue biphalin induces less physical dependence than morphine.

Authors:  M Yamazaki; T Suzuki; M Narita; A W Lipkowski
Journal:  Life Sci       Date:  2001-07-20       Impact factor: 5.037

Review 2.  Designing peptide receptor agonists and antagonists.

Authors:  Victor J Hruby
Journal:  Nat Rev Drug Discov       Date:  2002-11       Impact factor: 84.694

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.  Crystal structure of biphalin sulfate: a multireceptor opioid peptide.

Authors:  J L Flippen-Anderson; J R Deschamps; C George; V J Hruby; A Misicka; A W Lipkowski
Journal:  J Pept Res       Date:  2002-03

5.  Design and synthesis of inhibitors incorporating beta -amino acids of metalloendopeptidase EC 3.4.24.15.

Authors:  D L Steer; R A Lew; P Perlmutter; A I Smith; M I Aguilar
Journal:  J Pept Sci       Date:  2000-09       Impact factor: 1.905

6.  Stimulus-dependent specificity for annexin 1 inhibition of the inflammatory nociceptive response: the involvement of the receptor for formylated peptides.

Authors:  Stefano Pieretti; Amalia Di Giannuario; Milena De Felice; Mauro Perretti; Giuseppe Cirino
Journal:  Pain       Date:  2004-05       Impact factor: 6.961

7.  Synthesis of angiotensin II analogues by incorporating beta-homotyrosine or beta-homoisoleucine residues.

Authors:  K Stachowiak; M C Khosla; K Plucinska; P A Khairallah; F M Bumpus
Journal:  J Med Chem       Date:  1979-09       Impact factor: 7.446

8.  Identification of stabilized dynorphin derivatives for suppressing tolerance in morphine-dependent rats.

Authors:  Suliman I Al-Fayoumi; Boglarka Brugos; Vikram Arya; Esther Mulder; Barbel Eppler; Andre P Mauderli; Günther Hochhaus
Journal:  Pharm Res       Date:  2004-08       Impact factor: 4.200

9.  Hybrid alpha/beta3-peptides with proteinogenic side chains. Monosubstituted analogues of the chemotactic tripeptide For-Met-Leu-Phe-OMe.

Authors:  Cesare Giordano; Gino Lucente; Adriano Mollica; Marianna Nalli; Giampiero Pagani Zecchini; Mario Paglialunga Paradisi; Enrico Gavuzzo; Fernando Mazza; Susanna Spisani
Journal:  J Pept Sci       Date:  2004-08       Impact factor: 1.905

10.  In vitro quantitative study of the degradation of endomorphins.

Authors:  Csaba Tömböly; Antal Péter; Géza Tóth
Journal:  Peptides       Date:  2002-09       Impact factor: 3.750
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  9 in total

1.  Synthesis and Pharmacology of α/β(3)-Peptides Based on the Melanocortin Agonist Ac-His-dPhe-Arg-Trp-NH2 Sequence.

Authors:  Anamika Singh; Srinivasa R Tala; Viktor Flores; Katie Freeman; Carrie Haskell-Luevano
Journal:  ACS Med Chem Lett       Date:  2015-04-08       Impact factor: 4.345

2.  Novel cyclic biphalin analogue with improved antinociceptive properties.

Authors:  Adriano Mollica; Alfonso Carotenuto; Ettore Novellino; Antonio Limatola; Roberto Costante; Francesco Pinnen; Azzurra Stefanucci; Stefano Pieretti; Anna Borsodi; Reza Samavati; Ferenc Zador; Sándor Benyhe; Peg Davis; Frank Porreca; Victor J Hruby
Journal:  ACS Med Chem Lett       Date:  2014-07-14       Impact factor: 4.345

3.  Cyclic Biphalin Analogues Incorporating a Xylene Bridge: Synthesis, Characterization, and Biological Profile.

Authors:  Azzurra Stefanucci; Alfonso Carotenuto; Giorgia Macedonio; Ettore Novellino; Stefano Pieretti; Francesca Marzoli; Edina Szűcs; Anna I Erdei; Ferenc Zádor; Sándor Benyhe; Adriano Mollica
Journal:  ACS Med Chem Lett       Date:  2017-07-12       Impact factor: 4.345

4.  Structural and biological exploration of phe(3)-phe(4)-modified endomorphin-2 peptidomimetics.

Authors:  Giordano Lesma; Severo Salvadori; Francesco Airaghi; Thomas F Murray; Teresa Recca; Alessandro Sacchetti; Gianfranco Balboni; Alessandra Silvani
Journal:  ACS Med Chem Lett       Date:  2013-07-11       Impact factor: 4.345

5.  Developing Cyclic Opioid Analogues: Fluorescently Labeled Bioconjugates of Biphalin.

Authors:  Azzurra Stefanucci; Marilisa Pia Dimmito; Gabriela Molnar; John M Streicher; Ettore Novellino; Gokhan Zengin; Adriano Mollica
Journal:  ACS Med Chem Lett       Date:  2020-01-08       Impact factor: 4.345

6.  Unnarmicin D, an Anti-inflammatory Cyanobacterial Metabolite with δ and μ Opioid Binding Activity Discovered via a Pipeline Approach Designed to Target Neurotherapeutics.

Authors:  Riley D Kirk; Kassie Picard; Joseph A Christian; Shelby L Johnson; Brenton DeBoef; Matthew J Bertin
Journal:  ACS Chem Neurosci       Date:  2020-12-07       Impact factor: 4.418

7.  Synthesis and Pharmacological Evaluation of Hybrids Targeting Opioid and Neurokinin Receptors.

Authors:  Karol Wtorek; Anna Adamska-Bartłomiejczyk; Justyna Piekielna-Ciesielska; Federica Ferrari; Chiara Ruzza; Alicja Kluczyk; Joanna Piasecka-Zelga; Girolamo Calo'; Anna Janecka
Journal:  Molecules       Date:  2019-12-05       Impact factor: 4.411

8.  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

9.  β2-Homo-Amino Acid Scan of µ-Selective Opioid Tetrapeptide TAPP.

Authors:  Dagmara Tymecka; Piotr F J Lipiński; Piotr Kosson; Aleksandra Misicka
Journal:  Molecules       Date:  2020-05-25       Impact factor: 4.411
  9 in total

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