Unusual spin-trap chemistry for the reaction of hydroxyl radical with the carcinogen N-nitrosodimethylamine |
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| Affiliation: | 1. Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute, Frederick Cancer Research and Development Center, Frederick, MD 21702, U.S.A.;2. Ionizing Radiation Division, National Institute of Standards and Technology, Gaithersburg, MD 20899, U.S.A.;1. Department of Physics, Laboratory of Physical Chemistry of Materials and Environment, University of Ioannina, Ioannina 45110, Greece;2. Department of Chemistry, Laboratory of Inorganic Chemistry, University of Ioannina, Ioannina 45100, Greece;1. Department of Molecular Medicine, CMRI, School of Medicine, Kyungpook National University, Daegu 700-422, Republic of Korea;2. College of Pharmacy, CMRI, Research Institute of Pharmaceutical Sciences, Kyungpook National University, Daegu 702-701, Republic of Korea;3. ABRC, CMRI, School of Life Sciences, BK21 Plus KNU Creative BioResearch Group, Kyungpook National University, Daegu 702-701, Republic of Korea;1. School of Environmental Science and Technology, Sun Yat-sen University, Guangzhou, 510275, China;2. Guangdong Provincial Key Laboratory of Environmental Pollution and Remediation Technology, Guangdong Provincial Engineering Research Center for Heavy Metal Contaminated Soil Remediation, Guangzhou, 510275, China;3. Shenzhen Research Institute, Sun Yat-sen University, Shenzhen, 518057, China;1. Dept of Materials Science and Engineering, Yonsei University, 262 Seongsanno Seodaemun-gu, Seoul 129-749, South Korea;2. Institut Jean Lamour, UMR 7198CNRS, University of Lorraine 1, bd Arago CP 87811, 57078 Metz Cedex 3, France;1. Center of Excellence on Hazardous Substance Management, Department of Environmental Engineering, Faculty of Engineering, King Mongkut''s University of Technology Thonburi, Bangkok 10140, Thailand;2. Department of Environmental Engineering, Faculty of Engineering, King Mongkut''s University of Technology Thonburi, Bangkok 10140, Thailand;3. Environmental Research and Management Department, PTT Research and Technology Institute, Ayutthaya, Thailand;1. Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, C/Severo Ochoa s/n, 18071 Granada, Spain;2. Instituto de Investigación de Energías Renovables, Universidad de Castilla-La Mancha, Paseo de los Estudiantes s/n, 02071 Albacete, Spain;3. Departamento de Química Física y Analítica, Facultad de CC. Experimentales, Universidad de Jaén, Campus Las Lagunillas, s/n, 23071 Jaén, Spain;4. Departamento de Química Física, Facultad de Farmacia, Universidad de Castilla-La Mancha, Paseo de los Estudiantes s/n, 02071 Albacete, Spain |
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| Abstract: | The reaction of the potent carcinogen N-nitrosodimethylamine (NDMA) with hydroxyl radical generated via radiolysis was studied using EPR techniques. Attempts to spin trap NDMA radical intermediates with 3,5-dibromo-4-nitrosobenzene sulfonate (DBNBS) produced only unusual DBNBS radicals. One of these radicals was shown to be generated by both reaction of DBNBS with nitric oxide, and direct oxidation of DBNBS with an inorganic oxidant (.Br-2). Another DBNBS radical was identified as a sulfite spin adduct resulting from the degradation of DBNBS by a NDMA reactive intermediate. In the absence of DBNBS, hydroxyl radical reaction with NDMA gave the dimethylnitroxide radical. Unexpectedly, addition of DBNBS to a solution containing dimethylnitroxide produced an EPR spectrum nearly identical to that of NDMA solutions with DBNBS added before radiolysis. A proposed mechanism accounting for these observations is presented. |
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