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1-(3'-[125I]Iodophenyl)-3-methy-2-pyrazolin-5-one: preparation, solution stability, and biodistribution in normal mice.

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.
AuthorsYuuhei Sano, Tomokazu Motomura, Fumihiko Yamamoto, Miki Fukuda, Takahiro Mukai, Minoru Maeda
JournalChemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 58 Issue 8 Pg. 1020-5 (Aug 2010) ISSN: 1347-5223 [Electronic] Japan
PMID20686253 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • 1-(3'-iodophenyl)-3-methy-2-pyrazolin-5-one
  • Antioxidants
  • Pyrazolones
  • Edaravone
  • Antipyrine
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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