Literature DB >> 28835802

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

Azzurra Stefanucci1, Alfonso Carotenuto2, Giorgia Macedonio1, Ettore Novellino2, Stefano Pieretti3, Francesca Marzoli3, Edina Szűcs4, Anna I Erdei4, Ferenc Zádor4, Sándor Benyhe4, Adriano Mollica1.   

Abstract

In this work we enhanced the ring lipophilicity of biphalin introducing a xylene moiety, thus obtaining three cyclic regioisomers. Novel compounds have similar in vitro activity as the parent compound, but one of these (6a) shows a remarkable increase of in vivo antinociceptive effect. Nociception tests have disclosed its significant high potency and the more prolonged effect in eliciting analgesia, higher than that of biphalin and of the disulfide-bridge-containing analogue (7).

Entities:  

Keywords:  Biphalin; CLIPS technology; antinociception; opioids; xylene bridge

Year:  2017        PMID： 28835802      PMCID： PMC5554896          DOI： 10.1021/acsmedchemlett.7b00210

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  20 in total

1.  Spinal antinociceptive effects of AA501, a novel chimeric peptide with opioid receptor agonist and tachykinin receptor antagonist moieties.

Authors:  Iwona Maszczynska Bonney; Stacy E Foran; James E Marchand; Andrzej W Lipkowski; Daniel B Carr
Journal:  Eur J Pharmacol       Date:  2004-03-19       Impact factor: 4.432

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

Review 3.  Revolution in GPCR signalling: opioid receptor heteromers as novel therapeutic targets: IUPHAR review 10.

Authors:  Wakako Fujita; Ivone Gomes; Lakshmi A Devi
Journal:  Br J Pharmacol       Date:  2014-09       Impact factor: 8.739

Review 4.  Biphalin: The Foundation of Bivalent Ligands.

Authors:  Scott M Cowell; Yeon Sun Lee
Journal:  Curr Med Chem       Date:  2016       Impact factor: 4.530

5.  Synthesis and evaluation of disulfide bond mimetics of amylin-(1-8) as agents to treat osteoporosis.

Authors:  Renata Kowalczyk; Paul W R Harris; Margaret A Brimble; Karen E Callon; Maureen Watson; Jillian Cornish
Journal:  Bioorg Med Chem       Date:  2012-02-20       Impact factor: 3.641

6.  The biological consequences of replacing D-Ala in biphalin with amphiphilic α-alkylserines.

Authors:  Oliwia Frączak; Anika Lasota; Anna Leśniak; Andrzej W Lipkowski; Aleksandra Olma
Journal:  Chem Biol Drug Des       Date:  2014-03-24       Impact factor: 2.817

7.  Prolonged morphine treatment targets delta opioid receptors to neuronal plasma membranes and enhances delta-mediated antinociception.

Authors:  C M Cahill; A Morinville; M C Lee; J P Vincent; B Collier; A Beaudet
Journal:  J Neurosci       Date:  2001-10-01       Impact factor: 6.167

8.  Opioid Receptor Activity and Analgesic Potency of DPDPE Peptide Analogues Containing a Xylene Bridge.

Authors:  Azzurra Stefanucci; Ettore Novellino; Sako Mirzaie; Giorgia Macedonio; Stefano Pieretti; Paola Minosi; Edina Szűcs; Anna I Erdei; Ferenc Zádor; Sándor Benyhe; Adriano Mollica
Journal:  ACS Med Chem Lett       Date:  2017-03-14       Impact factor: 4.345

9.  A topochemical approach to explain morphiceptin bioactivity.

Authors:  T Yamazaki; S Ro; M Goodman; N N Chung; P W Schiller
Journal:  J Med Chem       Date:  1993-03-19       Impact factor: 7.446

10.  Protein modification, bioconjugation, and disulfide bridging using bromomaleimides.

Authors:  Mark E B Smith; Felix F Schumacher; Chris P Ryan; Lauren M Tedaldi; Danai Papaioannou; Gabriel Waksman; Stephen Caddick; James R Baker
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419
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  5 in total

1.  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

2.  Novel Cyclic Biphalin Analogues by Ruthenium-Catalyzed Ring Closing Metathesis: in Vivo and in Vitro Biological Profile.

Authors:  Azzurra Stefanucci; Wei Lei; Stefano Pieretti; Marilisa Pia Dimmito; Grazia Luisi; Ettore Novellino; Michał Nowakowski; Wiktor Koźmiński; Sako Mirzaie; Gokhan Zengin; John M Streicher; Adriano Mollica
Journal:  ACS Med Chem Lett       Date:  2019-03-08       Impact factor: 4.345

3.  Cyclic biphalin analogues with a novel linker lead to potent agonist activities at mu, delta, and kappa opioid receptors.

Authors:  Michael Remesic; Giorgia Macedonio; Adriano Mollica; Frank Porreca; Victor Hruby; Yeon Sun Lee
Journal:  Bioorg Med Chem       Date:  2018-05-26       Impact factor: 3.641

Review 4.  Biphalin-A Potent Opioid Agonist-As a Panacea for Opioid System-Dependent Pathophysiological Diseases?

Authors:  Patrycja Redkiewicz; Jolanta Dyniewicz; Aleksandra Misicka
Journal:  Int J Mol Sci       Date:  2021-10-21       Impact factor: 5.923

Review 5.  Peptidomimetics and Their Applications for Opioid Peptide Drug Discovery.

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

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