Literature DB >> 28699350

Analgesic Properties of Opioid/NK1 Multitarget Ligands with Distinct in Vitro Profiles in Naive and Chronic Constriction Injury Mice.

Joanna Starnowska1, Roberto Costante2, Karel Guillemyn2, Katarzyna Popiolek-Barczyk1, Nga N Chung3, Carole Lemieux3, Attila Keresztes4, Joost Van Duppen5, Adriano Mollica6, John Streicher4, Jozef Vanden Broeck5, Peter W Schiller3, Dirk Tourwé2, Joanna Mika1, Steven Ballet2, Barbara Przewlocka1.   

Abstract

The lower efficacy of opioids in span class="Chemical">pan class="Disease">neuropathic painspan> may be due to the increased activity of pronociceptive systems such as paspan>n class="Gene">substance P. We present evidence to support this hypothesis in this work from the spinal cord in a neuropathic pain model in mice. Biochemical analysis confirmed the elevated mRNA and protein level of pronociceptive substance P, the major endogenous ligand of the neurokinin-1 (NK1) receptor, in the lumbar spinal cord of chronic constriction injury (CCI)-mice. To improve opioid efficacy in neuropathic pain, novel compounds containing opioid agonist and neurokinin 1 (NK1) receptor antagonist pharmacophores were designed. Structure-activity studies were performed on opioid agonist/NK1 receptor antagonist hybrid peptides by modification of the C-terminal amide substituents. All compounds were evaluated for their affinity and in vitro activity at the mu opioid (MOP) and delta opioid (DOP) receptors, and for their affinity and antagonist activity at the NK1 receptor. On the basis of their in vitro profiles, the analgesic properties of two new bifunctional hybrids were evaluated in naive and CCI-mice, representing models for acute and neuropathic pain, respectively. The compounds were administered to the spinal cord by lumbar puncture. In naive mice, the single pharmacophore opioid parent compounds provided better analgesic results, as compared to the hybrids (max 70% MPE), raising the acute pain threshold close to 100% MPE. On the other hand, the opioid parents gave poor analgesic effects under neuropathic pain conditions, while the best hybrid delivered robust (close to 100% MPE) and long lasting alleviation of both tactile and thermal hypersensitivity. The results presented emphasize the potential of opioid/NK1 hybrids in view of analgesia under nerve injury conditions.

Entities:  

Keywords:  Hybrid peptides; NK1 antagonists; acute pain; neuropathic pain; opioid agonism

Mesh:

Substances:

Year:  2017        PMID: 28699350      PMCID: PMC5647227          DOI: 10.1021/acschemneuro.7b00226

Source DB:  PubMed          Journal:  ACS Chem Neurosci        ISSN: 1948-7193            Impact factor:   4.418


  40 in total

1.  Unsulfated C-terminal 7-peptide of cholecystokinin: a new ligand of the opiate receptor.

Authors:  P W Schiller; A Lipton; D F Horrobin; M Bodanszky
Journal:  Biochem Biophys Res Commun       Date:  1978-12-29       Impact factor: 3.575

Review 2.  The design of multitarget ligands for chronic and neuropathic pain.

Authors:  Szabolcs Dvoracsko; Azzurra Stefanucci; Ettore Novellino; Adriano Mollica
Journal:  Future Med Chem       Date:  2015-12-11       Impact factor: 3.808

3.  Increase in hemokinin-1 mRNA in the spinal cord during the early phase of a neuropathic pain state.

Authors:  T Matsumura; A Sakai; M Nagano; M Sawada; H Suzuki; M Umino; H Suzuki
Journal:  Br J Pharmacol       Date:  2008-07-28       Impact factor: 8.739

4.  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

5.  Inhibition of intracellular signaling pathways NF-κB and MEK1/2 attenuates neuropathic pain development and enhances morphine analgesia.

Authors:  Katarzyna Popiolek-Barczyk; Wioletta Makuch; Ewelina Rojewska; Dominika Pilat; Joanna Mika
Journal:  Pharmacol Rep       Date:  2014-05-19       Impact factor: 3.024

6.  Opioid activities of fragments of beta-endorphin and of its leucine65-analogue. Comparison of the binding properties of methionine- and leucine-enkephalin.

Authors:  A A Waterfield; F M Leslie; J A Lord; N Ling; H W Kosterlitz
Journal:  Eur J Pharmacol       Date:  1979-09-01       Impact factor: 4.432

7.  Anti-allodynic effects of peripheral delta opioid receptors in neuropathic pain.

Authors:  Noufissa Kabli; Catherine Marie Cahill
Journal:  Pain       Date:  2006-09-08       Impact factor: 6.961

8.  Derivation of a three-dimensional pharmacophore model of substance P antagonists bound to the neurokinin-1 receptor.

Authors:  Y Takeuchi; E F Shands; D D Beusen; G R Marshall
Journal:  J Med Chem       Date:  1998-09-10       Impact factor: 7.446

9.  Attenuation of morphine tolerance by minocycline and pentoxifylline in naive and neuropathic mice.

Authors:  Joanna Mika; Agnieszka Wawrzczak-Bargiela; Maria Osikowicz; Wioletta Makuch; Barbara Przewlocka
Journal:  Brain Behav Immun       Date:  2008-07-22       Impact factor: 7.217

Review 10.  Opioids for neuropathic pain.

Authors:  Ewan D McNicol; Ayelet Midbari; Elon Eisenberg
Journal:  Cochrane Database Syst Rev       Date:  2013-08-29
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2.  Bivalent ligand MCC22 potently attenuates nociception in a murine model of sickle cell disease.

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5.  Synthesis and Structure-Activity Relationships of 5'-Aryl-14-alkoxypyridomorphinans: Identification of a μ Opioid Receptor Agonist/δ Opioid Receptor Antagonist Ligand with Systemic Antinociceptive Activity and Diminished Opioid Side Effects.

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6.  CCR4 Antagonist (C021) Administration Diminishes Hypersensitivity and Enhances the Analgesic Potency of Morphine and Buprenorphine in a Mouse Model of Neuropathic Pain.

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7.  In Vivo, In Vitro and In Silico Studies of the Hybrid Compound AA3266, an Opioid Agonist/NK1R Antagonist with Selective Cytotoxicity.

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8.  Novel bifunctional hybrid compounds designed to enhance the effects of opioids and antagonize the pronociceptive effects of nonopioid peptides as potent analgesics in a rat model of neuropathic pain.

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10.  In Vitro Biological Evaluation of Aprepitant Based 177Lu-Radioconjugates.

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