137
Views
42
CrossRef citations to date
0
Altmetric
Original Article

Mechanism of Hydroxyl Radical Scavenging by Rebamipide: Identification of Mono-hydroxylated Rebamipide as a Major Reaction Product

, , &
Pages 487-494 | Received 29 Sep 2003, Published online: 07 Jul 2009

References

  • Haliwell, B. and Gutteridge, J.M.C. (1999) Free Radicals in Biology and Medicine, Third Edition (Oxford University Press, Oxford/New York).
  • Cheeseman, K.H. (1993) "Lipid peroxidation and cancer", In: Halliwell, B. and Arumoa, 0.I., eds, DNA and Free Radicals (Ellis Harwood, Chichester West, Sussex), pp 109–144.
  • Reinheckel, T., Nedelev, B., Prause, J., Augustin, W., Schulz, H.U., Lippert, H. and Halangk, W. (1998) "Occurrence of oxidatively modified proteins: an early event in experimental acute pancreatitis", Free Radic. Biol. Med. 24, 393–400.
  • Wallace, J.W. and Granger, D.N. (1996) "The cellular and molecular basis of gastric mucosal defense", FASEB J. 10, 731–740.
  • Zhang, Q.B., Nakashabendi, I.M., Mokhashi, US., Dawodu, J.B., Gemmell, C.G. and Russell, RI. (1996) "Association of cytotoxin production and neutrophil activation by strains of Helicobacter pylori isolated from patients with peptic ulceration and chronic gastritis", Gut 38, 841–845.
  • Vaananen, P.M., Meddings, J.B. and Wallace, J.L. (1991) "Role of oxygen-derived free radicals in indomethacin-induced gastric injury", Am. J. Physiol. 261, G470—G475.
  • Uchida, M., Tabusa, F., Komatsu, M., Morita, S., Kanbe, T. and Nakagawa, K. (1985) "Studies on 2(1H)-quinolinone deriva-tives as gastric antiulcer active agents. 2-(4-Chlorobenzoyl-amino)-342(1H)-quinolinon-4-yl] propionic acid and related compounds", Chem. Pharm. Bull. 33, 3775–3786.
  • Arakawa, T., Kobayashi, K., Yoshikawa, T. and Tarnawski, A. (1998) "Rebamipide: overview of its mechanisms of action and efficacy in mucosal protection and ulcer healing", Dig. Dis. Sci. 43, 5–13.
  • Kim, C.D. and Hong, K.W. (1995) "Preventive effect of rebamipide on gastric lesions induced by ischemia—reper-fusion in the rat", J. Pharmacol. Exp. Then 275, 340–344.
  • Sakurai, K. and Yamasaki, K. (1994) "Protective effect of rebamipide against hydrogen peroxide-induced hemorrhagic mucosal lesions in rat stomach", Jpn. J. Pharmacol. 64, 229–234.
  • Yoshikawa, T., Naito, Y., Nakamura, S., Nishimura, S., Kaneko, T., Iinuma, S., Takahashi, S., Kondo, M. and Yamasaki, K. (1993) "Effect of rebamipide on lipid peroxi-dation and gastric mucosal injury induced by indometacin in rats", Arzneim.-Forsch./Drug Res. 43, 1327–1330.
  • Yamasaki, K. and Sakurai, K. (1994) "Role of lipid peroxidation in protection of rats by rebamipide against gastric mucosal lesions induced by stress plus indometha-cin", Pathophysiology 1, 251–257.
  • Ogino, K., Hobara, T., Ishiyama, I., Yamasaki, K., Kobayashi, H., lzumi, Y. and Oka, S. (1992) "Antiulcer mechanism of action of rebamipide, a novel antiulcer compound, on diethyldithiocarbamate-induced antral gastric ulcers in rats", Fur. J. Pharmacol. 212, 9–13.
  • Kokura, S., Yoshikawa, T., Naito, Y., Ichikawa, H., Takano, H., Takahashi, S., Tomii, T., Yoshida, N. and Kondo, M. (1997) "Effects of rebamipide, a novel anti-ulcer agent, on gastric mucosal injury induced by platelet-activating factor in rats", Dig. Dis. Sci. 42, 2566–2571.
  • Suzuki, M., Miura, S., Mori, M., Kai, A., Suzuki, H., Fukumura, D., Suematsu, M. and Tsuchiya, M. (1994) "Rebamipide, a novel antiulcer agent, attenuates Helicobacter pylori induced gastric mucosal cell injury associated with neutrophil derived oxidants", Gut 35, 1375–1378.
  • Yoshikawa, T., Naito, Y., Tanigawa, T. and Kondo, M. (1993) "Free radical scavenging activity of the novel anti-ulcer agent rebamipide studied by electron spin resonance", Arzneim.-Forsch. Drug Res. 43, 363–366.
  • Naito, Y., Yoshikawa, T., Tanigawa, T., Sakurai, K., Yamasaki, K., Uchida, M. and Kondo, M. (1995) "Hydroxyl radical scavenging by rebamipide and related compounds: electron paramagnetic resonance study", Free Radic. Biol. Med. 18, 117–123.
  • Ali, M.A., Yasui, E, Matsugo, S. and Konishi, T. (2000) "The lactate-dependent enhancement of hydroxyl radical generation by Fenton reaction", Free Radic. Res. 32, 429–438.
  • Iwahashi, H., Ishii, T., Sugata, R. and Kido, R. (1990) "The effects of caffeic acid and its related catechols on hydroxyl radical formation by 3-hydroxyanthranilic acid, ferric chloride, and hydrogen peroxide", Arch. Biochem. Biophys. 276, 242–247.
  • Ueda, J., Saito, N., Shimazu, Y. and Ozawa, T. (1996) "A comparison of scavenging abilities of antioxidants against hydroxyl radicals", Arch. Biochem. Biophys. 333, 377–384.
  • Uchida, M., Tabusa, F., Komatsu, M., Morita, S., Kanbe, T. and Nakagawa, K. (1986) "Studies on 2(1H)-quinolinone deriva-tives as gastric antiulcer active agents. Synthesis and antiulcer activity of the metabolites of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl] propionic acid and related com-pounds", Chem. Pharm. Bull. 34, 4821–4824.
  • Shioya, Y, Kashiyama, E., Okada, K., Kusumoto, N., Abe, Y, Uchida, M. and Shimizu, T. (1989) "Metabolic fate of the anti-ulcer agent, (-± )-2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4y1] propionic acid (OPC-12759)—absorption, distribution and excretion in rats and dogs", Iyakuhin Kenkyu 20, 522–533, Abstract in English.
  • Halliwell, B. (1995) "Antioxidant characterization. Methodo-logy and mechanism", Biochem. Pharmacol. 49, 1341–1348.
  • Reiter, R.J., Tan, DX., Manchester, L.C. and Qi, W. (2001) "Biochemical reactivity of melatonin with reactive oxygen and nitrogen species: a review of the evidence", Cell Biochem. Biophys. 34, 237–256.
  • Bandyopadhyay, D., Biswas, K., Bandyopadhyay, U., Reiter, R.J. and Banerjee, R.K. (2000) "Melatonin protects against stress-induced gastric lesions by scavenging the hydroxyl radical", J. Pineal Res. 29, 143–151.
  • Tan, DA., Manchester, L.C., Reiter, R.J. and Plummer, B.F. (1999) "Cyclic 3-hydroxymelatonin: a melatonin metabolite generated as a result of hydroxyl radical scavenging", Biol. Signals Recept. 8, 70–74.
  • Yamasaki, K., Kanbe, T., Chijiwa, T., Ishiyama, H. and Morita, S. (1987) "Gastric mucosal protection by OPC-12759, a novel antiulcer compound, in the rat", Fur. J. Pharmacol. 142, 23–29.
  • Kleine, A., Kluge, S. and Peskar, B.M. (1993) "Stimulation of prostaglandin biosynthesis mediates gastroprotective effect of rebamipide in rats", Dig. Dis. Sci. 38, 1441–1449.
  • Aihara, M., Azuma, A., Takizawa, H., Tsuchimoto, D., Funakoshi, Y., Shindo, Y., Ohmoto, Y., Imagawa, K., Kikuchi, M., Mukaida, N. and Matsushima, K. (1998) "Molecular analysis of suppression of interleukin-8 production by rebamipide in Helicobacter pylori-stimulated gastric cancer cell lines", Dig. Dis. Sci. 43, 174–180.
  • Kim, H., Seo, J.Y. and Kim, K.H. (2000) "Inhibition of lipid peroxidation, NF-kappaB activation and IL-8 production by rebamipide in Helicobacter pylori-stimulated gastric epithelial cells", Dig. Dis. Sci. 45, 621–628.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.