NCX 2057, a novel NO-releasing derivative of ferulic acid, suppresses inflammatory and nociceptive responses in in vitro and in vivo models

Br J Pharmacol. 2009 Sep;158(2):569-79. doi: 10.1111/j.1476-5381.2009.00324.x. Epub 2009 Jul 7.

Abstract

Background and purpose: We previously reported that NCX 2057, a compound comprising a nitric oxide (NO)-releasing moiety and the natural antioxidant, ferulic acid (FA), inhibits pro-inflammatory mediators through NO-mediated gene regulation. Here, we have assessed the activities of NCX 2057 in models of inflammatory and neuropathic pain, and characterized its effects on cyclooxygenase (COX)-1 and COX-2.

Experimental approach: Anti-nociceptive and anti-inflammatory activities of NCX 2057 were measured in vitro and in vivo in models of inflammatory (carrageenan) and neuropathic (chronic constriction injury; CCI) pain. Effects of NCX 2057 were measured on COX-1 and COX-2 activities in RAW 264.7 macrophages.

Key results: NCX 2057 dose-dependently inhibited single motor unit responses to noxious mechanical stimulation (ID(50)= 100 micromol kg(-1)) and wind-up responses in rats with paw inflammation induced by carrageenan. Moreover, NCX 2057 inhibited allodynic responses following CCI of the sciatic nerve [ipsilateral Paw Withdrawal Threshold (g): vehicle: 41.4 +/- 3.3; NCX 2057: 76.3 +/- 4.8 FA: 37.9 +/- 15.5 at 175 micromol kg(-1)]. NCX 2057 reversed carrageenan-induced hyperalgesic responses in mice and inhibited prostaglandin E(2) formation in paw exudates. Finally, NCX 2057 competitively inhibited COX-1 and COX-2 activities in whole RAW macophages (IC(50)= 14.7 +/- 7.4 and 21.6 +/- 7.5 microM, respectively). None of these properties were exhibited by equivalent treatments with FA or standard NO donor compounds.

Conclusions and implications: These studies indicate that NCX 2057 is effective in chronic inflammatory and neuropathic pain models, probably because of its particular combination of anti-COX, antioxidant and NO-releasing properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Analgesics / administration & dosage
  • Analgesics / pharmacology
  • Animals
  • Anti-Inflammatory Agents / administration & dosage
  • Anti-Inflammatory Agents / pharmacology*
  • Antioxidants / administration & dosage
  • Antioxidants / pharmacology
  • Butanes / administration & dosage
  • Butanes / pharmacology*
  • Cyclooxygenase 1 / drug effects
  • Cyclooxygenase 1 / metabolism
  • Cyclooxygenase 2 / drug effects
  • Cyclooxygenase 2 / metabolism
  • Disease Models, Animal
  • Dose-Response Relationship, Drug
  • Inflammation / drug therapy*
  • Inflammation / physiopathology
  • Inhibitory Concentration 50
  • Macrophages
  • Male
  • Mice
  • Nitric Oxide / metabolism
  • Nitro Compounds / administration & dosage
  • Nitro Compounds / pharmacology*
  • Pain / drug therapy*
  • Pain / physiopathology
  • Rats
  • Rats, Wistar

Substances

  • 3-((4-hydroxy-3-methoxyphenyl)-2-propenoic acid 4-nitrooxy)butyl ester
  • Analgesics
  • Anti-Inflammatory Agents
  • Antioxidants
  • Butanes
  • Nitro Compounds
  • Nitric Oxide
  • Cyclooxygenase 1
  • Cyclooxygenase 2