Formation of the carboxamidine precursor of cyanuric acid from guanine oxidative lesion dehydro-guanidinohydantoin
| Autor: | Jérôme Trzcionka, Joris Irvoas, Geneviève Pratviel |
|---|---|
| Přispěvatelé: | Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées |
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Guanine
Stereochemistry DNA damage Clinical Biochemistry Amidines Pharmaceutical Science Oxidative phosphorylation 010402 general chemistry medicine.disease_cause Guanidines 01 natural sciences Biochemistry Peroxide 03 medical and health sciences chemistry.chemical_compound Residue (chemistry) Hydrolysis Drug Discovery medicine Organic chemistry [CHIM.COOR]Chemical Sciences/Coordination chemistry Molecular Biology 030304 developmental biology 0303 health sciences Molecular Structure Triazines Chemistry Hydantoins Organic Chemistry 0104 chemical sciences Oxidative Stress Molecular Medicine Cyanuric acid Oxidation-Reduction Oxidative stress |
| Zdroj: | Bioorganic and Medicinal Chemistry Bioorganic and Medicinal Chemistry, Elsevier, 2014, 22 (17), pp.4711-4716. ⟨10.1016/j.bmc.2014.07.010⟩ |
| ISSN: | 0968-0896 1464-3391 |
| Popis: | International audience; DNA damage under oxidative stress leads to oxidation of guanine base. The identification of the resulting guanine lesions in cellular DNA is difficult due to the sensitivity of the primary oxidation products to hydrolysis and/or further oxidation. We isolated dehydroguanidino-hydantoin (DGh) (or oxidized guanidinohydantoin), a secondary oxidation product of guanine, and showed that this lesion reacts readily with nucleophiles such as asymmetric peroxides and transforms to 2,4,6-trioxo-1,3,5-triazinane-1-carboxamidine residue. Further hydrolysis of this intermediate leads to cyanuric acid and finally to urea residue. This work demonstrates a new possible pathway for the formation of the well-known carboxamidine precursor of cyanuric acid lesion. |
| Databáze: | OpenAIRE |
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