Abstract |
3-Methyl-1-phenyl-2-pyrazolin-5-one ( edaravone, 1), known as a potent free radical scavenger, has been developed as a medical drug for the treatment of acute cerebral infarction. With the aim of developing radiotracers for imaging free radicals in vivo, 1-(3'-[(125)I]iodophenyl)-3-methy-2-pyrazolin-5-one ((125)I-2) was synthesized by two methods, via isotopic exchange and interhalogen exchange under solvent-free conditions, in which iodo- and bromo-derivatives were used as labeling precursors, respectively. After HPLC purification, (125)I-2 was obtained in modest isolated radiochemical yields (ca. 20%) with high radiochemical purities by both methods. The former gave specific activities of 0.2-0.6 kBq/micromol, whereas the latter approach achieved specific activities of more than 0.14 GBq/micromol. On attempting to prepare an injectable formulation for (125)I-2 with high specific activity, its radiochemical purities dropped to about 60-70%. Unlabeled analog 2 was found to have lipophilic and antioxidant properties similar to edaravone. Intravenous injection of (125)I-2 with low specific radioactivity into normal mice showed signs of distribution profiles similar to reported results for (14)C-labeled edaravone in normal rats.
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Authors | Yuuhei Sano, Tomokazu Motomura, Fumihiko Yamamoto, Miki Fukuda, Takahiro Mukai, Minoru Maeda |
Journal | Chemical & pharmaceutical bulletin
(Chem Pharm Bull (Tokyo))
Vol. 58
Issue 8
Pg. 1020-5
(Aug 2010)
ISSN: 1347-5223 [Electronic] Japan |
PMID | 20686253
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- 1-(3'-iodophenyl)-3-methy-2-pyrazolin-5-one
- Antioxidants
- Pyrazolones
- Edaravone
- Antipyrine
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Topics |
- Animals
- Antioxidants
(administration & dosage, chemical synthesis, chemistry, pharmacokinetics)
- Antipyrine
(administration & dosage, analogs & derivatives, chemical synthesis, chemistry, pharmacokinetics)
- Drug Stability
- Edaravone
- Male
- Mice
- Mice, Inbred ICR
- Molecular Structure
- Pyrazolones
(administration & dosage, chemical synthesis, chemistry, pharmacokinetics)
- Solubility
- Tissue Distribution
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