Photoinduced reactions of anthraquinone antitumor agents with peptides and nucleic acid bases: an electron spin resonance and spin trapping study |
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| Authors: | A J Carmichael P Riesz |
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| Affiliation: | 1. Department of Chemistry, Indian Institute of Technology Jodhpur, NH 65, Karwar, Jodhpur, India 342037;2. Department of Chemistry, SRM Institute of Science and Technology, Kattankulathur, Chennai, India 603203;3. Department of Physics and Nanotechnology, SRM Institute of Science and Technology, Kattankulathur, Chennai, India 603203;4. Division of Energy and Environment, Inventus Bio Energy Private Limited, Chengalpattu, Tamil Nadu, India 603111;1. Division of Biochemistry, FBSc, Sher-e-Kashmir University of Agricultural Sciences and Technology of Jammu, Jammu, India;2. Department of Botany, School of Biological Sciences, University of Kashmir, Srinagar, India;3. Division of Floriculture and Landscape Architecture, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir, Srinagar, India;4. Division of Fruit Science, Faculty of Horticulture, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir, Srinagar, India;1. Departamento de Bioquímica, Instituto Nacional de Cardiología, Mexico;2. Departamento de Fisiología, Instituto Nacional de Cardiología, Mexico;1. Department of Chemistry, University of Cyprus, Nicosia 1678, Cyprus;2. Cyprus University of Technology, Department of Agricultural Production, Biotechnology and Food Science, Limassol 3036, Cyprus;3. Department of Physiology, Faculty of Medicine, School of Health Sciences, University of Ioannina, Ioannina 45110, Greece;4. Maxillofacial Surgery, Faculty of Medicine, School of Health Sciences, University of Ioannina, Ioannina, Greece;5. Department of Nursing, School of Health Sciences, University of Ioannina, Ioannina 45110, Greece;1. BioTalentum Ltd., Gödöllő, Hungary;2. Molecular Animal Biotechnology Laboratory, Szent István University, Gödöllő, Hungary |
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| Abstract: | The photoexcitation (lambda = 313 +/- 10 nm) of adriamycin, daunomycin, and mitoxantrone in the presence of peptides or pyrimidine nucleic acid bases was investigated. In air-saturated and air-free solutions, peptides are decarboxylated by the photoexcited drug molecules. The decarboxylation reactions were shown to occur specifically at the C-terminal amino acid of the peptide. The decarboxylated peptide radicals were spin-trapped using 2-methyl-2-nitrosopropane (MNP) and identified by electron spin resonance (ESR). In air-free solutions, nucleic acid bases are oxidized by the photoexcited drug molecules predominantly generating C(5)-carbon-centered radicals in the pyrimidine rings of uracil, cytosine, and thymine. However, spin adducts of MNP and thymine were also obtained at the N(1) or N(3) positions of the pyrimidine ring. In air-saturated adriamycin and daunomycin solutions, the spin adducts of MNP with uracil or thymine are similar to those obtained following hydroxyl radical reactions with these pyrimidines. This suggests that in the presence of oxygen, the photoexcited adriamycin and daunomycin transfer an electron to oxygen generating the superoxide anion radicals (O2-.), which are precursors of hydroxyl radicals. O2-. was also formed when O2-saturated DNA solutions were photoirradiated (lambda = 313 +/- 10 and 438 +/- 10 nm) in the presence of adriamycin and daunomycin, indicating that the photodegradation of DNA in the presence of these drugs caused by hydroxyl radicals is mediated by dissolved oxygen. |
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