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A pulse radiolysis study of free radicals formed by one electron oxidation of the antimalarial drug pyronaridine

Ismail, FMD, Drew, MGB, Navaratnam, S and Bisby, RH 2009, 'A pulse radiolysis study of free radicals formed by one electron oxidation of the antimalarial drug pyronaridine' , Research on Chemical Intermediates, 35 (4) , pp. 363-377.

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          Abstract

          Free radicals from one-electron oxidation of the antimalarial drug pyronaridine have been studied by pulse radiolysis. The results show that pyronaridine is readily oxidised to an intermediate semiiminoquine radical by inorganic and organic free radicals, including those derived from tryptophan and acetaminophen. The pyronaridine radical is rapidly reduced by both ascorbate and caffeic acid. The results indicate that the one-electron reduction potential of the pyronaridine radical at neutral pH lies between those of acetaminophen (707 mV) and caffeic acid (534 mV). The pyronaridine radical decays by a second order process which DFT calculations (UB3LYP/6-31+G* ) suggest is a disproportionation reaction. Important calculated dimensions of pyronaridine, its phenoxyl and aminyl radical as well as the iminoquinone are presented.

          Item Type: Article
          Uncontrolled Keywords: Pyronaridine, free radical, pulse radiolysis, oxidation, DFT, antimalarial
          Themes: Health and Wellbeing
          Schools: Colleges and Schools > College of Science & Technology > School of Environment and Life Sciences > Ecosystems and Environment Research Centre
          Colleges and Schools > College of Science & Technology > School of Environment and Life Sciences
          Journal or Publication Title: Research on Chemical Intermediates
          Publisher: Kluwer
          Refereed: Yes
          ISSN: 0922-6168
          Depositing User: RH Bisby
          Date Deposited: 28 Sep 2011 12:09
          Last Modified: 20 Aug 2013 18:10
          URI: http://usir.salford.ac.uk/id/eprint/17768

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