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

British Journal of Pharmacology

Volumn 158, Issue 2, 2009, Pages 569-579

  Ronchetti, Daniela ^a   Borghi, Valentina ^a   Gaitan, Gema ^b   Herrero, Juan F ^b   Impagnatiello, Francesco ^a  

^a NicOx Research Institute   (Italy)

^b UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

Cyclooxygenase; Ferulic acid; Inflammation; NCX 2057; Nitric oxide; Nociception

Indexed keywords

3 (4 HYDROXY 3 METHOXYPHENYL) 2 PROPENOIC ACID 4 (NITROOXY)BUTYL ESTER; CARRAGEENAN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; FERULIC ACID; FERULIC ACID DERIVATIVE; GABAPENTIN; NALOXONE; NAPROXEN; NCX 2057; NITRIC OXIDE; NITRIC OXIDE DONOR; PROSTAGLANDIN E2; S NITROSOGLUTATHIONE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG MECHANISM; IC 50; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; MALE; MECHANICAL STIMULATION; MOTOR UNIT; MOUSE; NEUROPATHIC PAIN; NOCICEPTION; NONHUMAN; PRIORITY JOURNAL; RAT; WITHDRAWAL REFLEX;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTIOXIDANTS; BUTANES; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; INFLAMMATION; INHIBITORY CONCENTRATION 50; MACROPHAGES; MALE; MICE; NITRIC OXIDE; NITRO COMPOUNDS; PAIN; RATS; RATS, WISTAR;

EID: 69549084686     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2009.00324.x     Document Type: Article

References (48)

1. Aggarwal BB, Sung B (2009). Pharmacological basis for the role of curcumin in chronic diseases: an age-old spice with modern targets. Trends Pharmacol Sci 2 : 79 84.
2. Alique M, Lucio FJ, Herrero JF (2006). Vitamin A active metabolite, all-trans retinoic acid, induces spinal cord sensitization. II. Effects after intrathecal administration. Br J Pharmacol 149 : 65 72. (Pubitemid 44299069)
3. Bennet GJ, Xie YK (1988). A peripheral mononeuropathy in rat that produces disorders of pain sensation like those seen in man. Pain 33 : 87 107.
4. Burian M, Geisslinger G (2005). COX-dependent mechanisms involved in the antinociceptive action of NSAIDs at central and peripheral sites. Pharmacol Ther 107 : 139 154.
5. Chaplan SR, Bach FW, Pogrel JW, Chung JM, Yaksh TL (1994). Quantitative assessment of tactile allodynia in the rat paw. J Neurosci Methods 53 : 55 63.
6. Crisp T, Minus TO, Coleman ML, Giles JR, Cibula C, Finnerty EP (2006). Aging, peripheral nerve injury and nociception: effects of the antioxidant 16-desmethyltirilazad. Behav Brain Res 166 : 159 165.
7. Daemen MA, Kurvers HA, Kitslaar PJ, Slaaf DW, Bullens PH, Van den Wildenberg FA (1998). Neurogenic inflammation in an animal model of neuropathic pain. Neurol Res 20 : 41 45.
8. Dong WG, Mei Q, Yu JP, Xu JM, Xiang L, Xu Y (2003). Effects of melatonin on the expression of iNOS and COX-2 in rat models of colitis. World J Gastroenterol 9 : 1307 1311.
9. Durate ID, Lorenzetti BB, Ferreira SH (1990). Peripheral analgesia and activation of the nitric oxide-cyclic GMP pathway. Eur J Pharmacol 186 : 289 293.
10. Figueroa-Romero C, Sadidi M, Feldman EL (2008). Mechanisms of disease: the oxidative stress theory of diabetic neuropathy. Rev Endocr Metab Disord 9 : 301 314.
11. Govoni M, Casagrande S, Maucci R, Chiroli V, Tocchetti P (2006). In vitro metabolism of (nitrooxy)butyl ester nitric oxide-releasing compounds: comparison with glyceryl trinitrate. J Pharmacol Exp Ther 317 : 752 761.
12. 2 synthase-1. J Biol Chem 279 : 24866 24872.
13. Guedes RP, Bosco LD, Teixeira CM, Araujo AS, Llesuy S, Bello-Klein A et al. (2006). Neuropathic pain modifies antioxidant activity in rat spinal cord. Neurochem Res 31 : 603 609.
14. Hancock CM, Riegger-Krugh C (2008). Modulation of pain in osteoarthritis: the role of nitric oxide. Clin J Pain 24 : 353 365.
15. Hara S, Kuhns ER, Ellenberger EA, Mueller JL, Shibuya T, Endo T et al. (1995). Involvement of nitric oxide in intracerebroventricular beta-endorphin-induced neuronal release of methionine-enkephalin. Brain Res 675 : 190 194.
16. Herrero JF, Cervero F (1996). Changes in nociceptive reflex facilitation during carrageenan-induced arthritis. Brain Res 717 : 62 68.
17. Herrero JF, Headley PM (1991). The effects of sham and full spinalization on the systemic potency of μ- and k-opioids on spinal nociceptive reflexes in rats. Br J Pharmacol 104 : 166 170.
18. Herrero JF, Laird JM, Lopez-Garcia JA (2000). Wind-up of spinal cord neurones and pain sensation: much ado about something? Prog Neurobiol 61 : 169 203.
19. Hoffmann C (2000). COX-2 in brain and spinal cord implications for therapeutic use. Curr Med Chem 7 : 1113 1120.
20. Hosoda A, Ozaki Y, Kashiwada A, Mutoh M, Wakabayashi K, Mizuno K et al. (2002). Syntheses of ferulic acid derivatives and their suppressive effects on cyclooxygenase-2 promoter activity. Bioorg Med Chem 10 : 1189 1196.
21. Ibuki T, Matsumura K, Yamazaki Y, Nozaki T, Tanaka Y, Kobayashi S (2003). Cyclooxygenase-2 is induced in the endothelial cells throughout the central nervous system during carrageenan-induced hind paw inflammation; its possible role in hyperalgesia. J Neurochem 86 : 318 328.
22. Jain NK, Patil CS, Singh A, Kulkarni SK (2001). Sildenafil-induced peripheral analgesia and activation of the nitric oxide-cyclic GMP pathway. Brain Res 909 : 170 178.
23. Khalil Z, Khodr B (2001). A role for free radicals and nitric oxide in delayed recovery in aged rats with chronic constriction nerve injury. Free Radic Biol Med 31 : 430 439.
24. Kean WF, Buchanan WW (2005). The use of NSAIDs in rheumatic disorders 2005: a global perspective. Inflammopharmacology 13 : 343 370.
25. Lin Q, Wu J, Peng YB, Cui M, Willis WD (1999). Inhibition of primate spinothalamic tract neurons by spinal glycine and GABA is modulated by guanosine 3′-5′-cyclic monophosphate guanosine. J Neurophysiol 81 : 1093 1103.
26. Maihofner C, Tegeder I, Euchenhofer C, deWitt D, Brune K, Bang R et al. (2000). Localization and regulation of cyclo-oxygenase-1 and -2 and neuronal nitric oxide synthase in mouse spinal cord. Neurosci 101 : 1093 1108.
27. Ndengele MM, Cuzzocrea S, Esposito E, Mazzon E, Di Paola R, Matuschak GM et al. (2008). Cyclooxygenases 1 and 2 contribute to peroxynitrite-mediated inflammatory pain hypersensitivity. FASEB J 22 : 3154 3164.
28. Ongini E, Impagnatiello F, Bonazzi A, Guzzetta M, Govoni M, Monopoli A et al. (2004). Nitric oxide (NO)-releasing statin derivatives, a class of drugs showing enhanced antiproliferative and antiinflammatory properties. Proc Natl Acad Sci USA 101 : 8497 8502.
29. Patrignani P, Tacconelli S, Sciulli MG, Capone ML (2005). New insights into COX-2 biology and inhibition. Brain Res Brain Res Rev 48 : 352 359.
30. Poole S, Lorenzetti BB, Cunha JM, Cunha FQ, Ferreira SH (1999). Bradykinin B1 and B2 receptors, tumour necrosis factor alpha and inflammatory hyperalgesia. Br J Pharmacol 126 : 649 656.
31. Portanova JP, Zhang Y, Anderson GD, Hauser SD, Masferrer JL, Seibert K et al. (1996). Selective neutralization of prostaglandin E2 blocks inflammation, hyperalgesia, and interleukin 6 production in vivo. J Exp Med 184 : 883 891.
32. Reinold H, Ahmadi S, Depner UB, Layh B, Heindl C, Hamza M et al. (2005). Spinal inflammatory hyperalgesia is mediated by prostaglandin E receptors of the EP2 subtype. J Clin Invest 115 : 673 679.
33. Romero-Sandoval EA, Alique M, Moreno-Manzano V, Molina C, Lucio FJ, Herrero JF (2004). The oral administration of retinoic acid enhances nociceptive withdrawal reflexes in rats with soft-tissue inflammation. Inflamm Res 53 : 297 303.
34. Ronchetti D, Impagnatiello F, Guzzetta M, Gasparini L, Borgatti M, Gambari R et al. (2006). Modulation of iNOS expression by a nitric oxide-releasing derivative of the natural antioxidant ferulic acid in activated RAW 264.7 macrophages. Eur J Pharmacol 532 : 162 169.
35. Scholz J, Woolf CJ (2007). The neuropathic pain triad: neurons, immune cells and glia. Nat Neurosci 10 : 1361 1368.
36. Seybold VS, Jia YP, Abrahams LG (2003). Cyclo-oxygenase-2 contributes to central sensitization in rats with peripheral inflammation. Pain 105 : 47 55.
37. Sharma S, Kulkarni SK, Chopra K (2006). Resveratrol, a polyphenolic phytoalexin attenuates thermal hyperalgesia and cold allodynia in STZ-induced diabetic rats. Indian J Exp Biol 44 : 566 569.
38. Simmons DL, Botting RM, Hla T (2004). Cyclooxygenase isozymes: the biology of prostaglandin synthesis and inhibition. Pharmacol Rev 56 : 387 437.
39. Solano RE, Herrero JF (1997). Cutaneous responsiveness of rat single motor units activated by natural stimulation. J Neurosci Methods 73 : 135 140.
40. Svensson CI, Yaksh TL (2002). The spinal phospholipase-cyclooxygenase- prostanoid cascade in nociceptive processing. Annu Rev Pharmacol Toxicol 42 : 553 583.
41. Tankova T, Cherninkova S, Koev D (2005). Treatment for diabetic mononeuropathy with alpha-lipoic acid. Int J Clin Pract 59 : 645 650.
42. Valsecchi AE, Franchi S, Panerai AE, Sacerdote P, Trovato AE, Colleoni M (2008). Genistein, a natural phytoestrogen from soy, relieves neurophatic pain following chronic constriction sciatic nerve injury in mice: anti-inflammatory and antioxidant activity. J Neurochem 107 : 230 240.
43. Vane JR (1971). Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol 231 : 232 235.
44. Vane JR, Bakhle YS, Botting RM (1998). Cyclooxygenases 1 and 2. Annu Rev Pharmacol Toxicol 38 : 97 120.
45. Warner TD, Mitchell JA (2002). Cyclooxygenase-3 (COX-3): filling in the gaps towards a COX continuum? Proc Natl Acad Sci USA 99 : 13371 13373.
46. Wenk GL, McGann-Gramling K, Hauss-Wegrzyniak B, Ronchetti D, Maucci R, Rosi S et al. (2004). Attenuation of chronic neuroinflammation by a nitric oxide-releasing derivative of the antioxidant ferulic acid. J Neurochem 89 : 484 493.
47. Willingale HL, Gardiner NJ, McLymont N, Giblett S, Grubb BD (1997). Prostanoids synthesized by cyclo-oxygenase isoforms in rat spinal cord and their contribution to the development of neuronal hyperexcitability. Br J Pharmacol 122 : 1593 1604.
48. Wu WP, Hao JX, Ongini E, Impagnatiello F, Presotto C, Wiesenfeld-Hallin Z et al. (2004). A nitric oxide (NO)-releasing derivative of gabapentin, NCX 8001, alleviates neuropathic pain-like behavior after spinal cord and peripheral nerve injury. Br J Pharmacol 141 : 65 74.