The Reaction Rate of Edaravone (3-Methyl-1-phenyl-2-pyrazolin-5-one (MCI-186)) with Hydroxyl Radical

Abe, Shinji; Kirima, Kazuyoshi; Tsuchiya, Koichiro; Okamoto, Momoko; Hasegawa, Takehisa; Yoshizumi, Masanori; Takahashi, Toshiaki

doi:10.1248/cpb.52.186

Cited by 72 publications

(59 citation statements)

References 42 publications

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“…7). Edaravone (MCI-186), a novel neuroprotective agent approved for the acute therapy of embolic stroke, 36) has been reported to scavenge DPPH radical 37,38) and hydroxyl radical 38,39) but not superoxide anion. 39) Thus effective antioxidants are not required to react with all types of radicals.…”

Section: Discussionmentioning

confidence: 99%

Characterization of the Radical-Scavenging Reaction of 2-O-Substituted Ascorbic Acid Derivatives, AA-2G, AA-2P, and AA-2S: A Kinetic and Stoichiometric Study

Takebayashi

Tai

Gohda

et al. 2006

Biological & Pharmaceutical Bulletin

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The aim of this study was to characterize the antioxidant activity of three ascorbic acid (AA) derivatives Osubstituted at the C-2 position of AA: ascorbic acid 2-glucoside (AA-2G), ascorbic acid 2-phosphate (AA-2P), and ascorbic acid 2-sulfate (AA-2S). The radical-scavenging activities of these AA derivatives and some common low molecular-weight antioxidants such as uric acid or glutathione against 1,1-diphenyl-picrylhydrazyl (DPPH) radical, 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS˙؉), or galvinoxyl radical were kinetically and stoichiometrically evaluated under pH-controlled conditions. Those AA derivatives slowly and continuously reacted with DPPH radical and ABTS˙؉, but not with galvinoxyl radical. They effectively reacted with DPPH radical under acidic conditions and with ABTS˙؉ under neutral conditions. In contrast, AA immediately quenched all species of radicals tested at all pH values investigated. The reactivity of Trolox, a water-soluble vitamin E analogue, was comparable to that of AA in terms of kinetics and stoichiometrics. Uric acid and glutathione exhibited long-lasting radical-scavenging activity against these radicals under certain pH conditions. The radical-scavenging profiles of AA derivatives were closer to those of uric acid and glutathione rather than to that of AA. The number of radicals scavenged by one molecule of AA derivatives, uric acid, or glutathione was equal to or greater than that by AA or Trolox under the appropriate conditions. These data suggest the potential usage of AA derivatives as radical scavengers.

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Section: Discussionmentioning

confidence: 99%

Characterization of the Radical-Scavenging Reaction of 2-O-Substituted Ascorbic Acid Derivatives, AA-2G, AA-2P, and AA-2S: A Kinetic and Stoichiometric Study

Takebayashi

Tai

Gohda

et al. 2006

Biological & Pharmaceutical Bulletin

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“…In the other hand, the mixtures containing NO-NIF and unsaturated lipids have electrons to offer electrophiles. 51) The scavenging activity against 13-HPODE increased in the order of nifedipine, NO-NIF, and NO-NIF plus linolenic acid (Fig. 2).…”

Section: Epr Spectra Of No-nif-derived Radicals In the Presence Of Humentioning

confidence: 91%

Antioxidant Effects of Photodegradation Product of Nifedipine

Horinouchi

Tsuchiya

Taoka

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Therefore antioxidants that counteract the effects of ROS are supposed to exert neuroprotective effects. Edaravone has shown in vitro antioxidant activity against ROS such as singlet oxygen [54], hydroxyl radical [55,56] and other ROS [57]. Edaravone has been reported to reduce oxidative damage in rodents' brain after ischemic injury [58] (reviewed by Watanabe and colleagues [51]).…”

Section: Reactive Oxygen Speciesmentioning

confidence: 99%

Clinical and pharmacological aspects of bath salt use: A review of the literature and case reports

Miotto¹,

Striebel²,

Cho

et al. 2013

Drug and Alcohol Dependence

121

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Abstract:Reactive oxygen species (ROS) are widely believed to cause or aggravate several human pathologies such as neurodegenerative diseases, cancer, stroke and many other ailments. Antioxidants are assumed to counteract the harmful effects of ROS and therefore prevent or treat oxidative stress-related diseases. In this report, recent human studies exploring the efficiency of antioxidants in prevention and treatment of various diseases are reviewed. Few antioxidants including edaravone (for ischemic stroke in Japan), Nacetylcysteine (for acetaminophen toxicity), alfa-lipoic acid (for diabetic neuropathy) and some flavonoids (polyphenolic compounds present in dietary plants), such as micronized purified flavonoid fraction (diosmin and hesperidin) and oxerutins (for chronic venous insufficiency) as well as baicalein and catechins (for osteoarthritis) have found accepted clinical use. However, despite much enthusiasm in the 1980s and 1990s, many well-known agents such as antioxidant vitamins and also more recently developed compounds such as nitrones have not successfully passed the scrutiny of clinical trials for prevention and treatment of various diseases. This has given rise to a pessimistic view of antioxidant therapy, however, the evidence from human epidemiological studies about the beneficial effects of dietary antioxidants and preclinical in vitro and animal data are compelling. We have probably wasted too much time on agents like antioxidant vitamins instead of focusing on more disease specific, target-directed, highly bioavailable antioxidants. We here discuss possible reasons for the lack of success in some clinical trials and seek to provide some suggestions to be considered if antioxidant therapy is to succeed as an effective therapeutic strategy.

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The Reaction Rate of Edaravone (3-Methyl-1-phenyl-2-pyrazolin-5-one (MCI-186)) with Hydroxyl Radical

Cited by 72 publications

References 42 publications

Characterization of the Radical-Scavenging Reaction of 2-O-Substituted Ascorbic Acid Derivatives, AA-2G, AA-2P, and AA-2S: A Kinetic and Stoichiometric Study

Characterization of the Radical-Scavenging Reaction of 2-O-Substituted Ascorbic Acid Derivatives, AA-2G, AA-2P, and AA-2S: A Kinetic and Stoichiometric Study

Antioxidant Effects of Photodegradation Product of Nifedipine

Clinical and pharmacological aspects of bath salt use: A review of the literature and case reports

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