A pulse radiolysis study of free radicals formed by one-electron oxidation of the antimalarial drug pyronaridine |
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| Authors: | Fyaz M. D. Ismail Michael G. B. Drew Suppiah Navaratnam Roger H. Bisby |
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| Affiliation: | (1) School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Liverpool, L3 3AF, UK;(2) Department of Chemistry, University of Reading, Reading, RG6 6AD, UK;(3) Biomedical Sciences Research Institute, University of Salford, Salford, M5 4WT, UK;(4) Free Radical Research Facility, STFC Daresbury Laboratory, Warrington, WA4 4AD, UK |
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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 semi-iminoquine 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 to produce the iminoquinone, detected by electrospray mass spectrometry, in a second-order process that density functional theory (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. Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users. |
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| Keywords: | Pyronaridine Free radical Pulse radiolysis Oxidation DFT Antimalarial |
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