Antioxidant properties of 2-imidazolones and 2-imidazolthiones |
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| Authors: | R C Smith J C Reeves R C Dage R A Schnettler |
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| Institution: | 1. Department of Animal and Dairy Sciences, Alabama Agricultural Experiment Station, Auburn University, AL 36849, U.S.A.;2. Richard C. Dage and Richard A. Schnettler Merrell Dow Research Center, Merrell Dow Pharmaceuticals, Inc., Cincinnati, OH 45215, U.S.A.;1. Department of Biomedical Sciences, Catholic Kwandong University, Gangneung, 25601, Republic of Korea;2. Department of Animal Resources Science, Dankook University, Cheonan, 330-714, Republic of Korea;3. Center for Animal Biotechnology and Genomics and Department of Animal Science, Texas A&M University, College Station, 77843-2471, Texas, USA;1. College of Veterinary Medicine and Biomedical Sciences, Texas A&M University, College Station, TX 77843-4466, USA;2. Barz IVF Center for Embryo Research and Infertility Treatment, Koya Street, Brayati, Erbil 44001, Kurdistan, Iraq;3. US Army Research and Development Center – USACE, 3909 Halls Ferry Rd., Vicksburg, MS 39180, USA;1. Department of Biology and Chemistry, Nipissing University, North Bay, ON P1B 8L7, Canada;2. Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan 333031, India;1. Grupo de Química Organometálica, Departamento de Química Inorgánica, Facultad de Química, Universidad de Murcia, Spain;2. ACTI, Universidad de Murcia, E-30100, Murcia, Spain |
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| Abstract: | Uric acid has been postulated to be an important antioxidant and free radical scavenger in humans. Other purines, such as xanthine, that lack an 8-oxo group on the imidazole ring do not show antioxidant properties. For this reason, the antioxidative activities of 2-imidazolones and 2-imidazolthiones were compared to that of uric acid. 2-Imidazolthiones reacted with the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH) at rates comparable to those of uric acid and other antioxidants. 2-Imidazolones also reacted with DPPH, although at a much slower rate than the 2-imidazolthiones. The 2-imidazolthiones protected oxyhemoglobin from oxidation to methemoglobin by sodium nitrite; the 2-imidazolones had little effect on the oxidation of oxyhemoglobin by nitrate. Most of the 2-imidazolthiones and 2-imidazolones protected both porcine and bovine erythrocytes from hemolysis by t-butyl hydroperoxide. Although 2-imidazolthiones were more reactive than 2-imidazolones in the assays using DPPH and the oxidation of oxyhemoglobin, both types of compounds may be useful as antioxidants in vivo. |
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