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Original Article

Specific Deprotonation Reactions of the Pyrimidine Radical Cation Resulting from the Menadione Mediated Photosensitization of 2′-Deoxycytidine

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Pages 295-301 | Received 21 Jul 1986, Published online: 07 Jul 2009

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Jean Cadet, J. Richard Wagner, Vladimir Shafirovich & Nicholas E. Geacintov. (2014) One-electron oxidation reactions of purine and pyrimidine bases in cellular DNA. International Journal of Radiation Biology 90:6, pages 423-432.
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A. A. SHAW. (1996) Direct effects of gamma-radiation on 2-deoxycytidine in frozen aqueous solution. International Journal of Radiation Biology 70:1, pages 1-6.
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R. Rashid, F. Mark, H.-P. Schuchmann & C. von Sonntag. (1991) SO·−4-induced Oxidation of 1,3,6-trimethyluracil and 1,3,5-trimethyluracil (1,3-dimethylthymine) by Potassium Peroxodisulphate in Aqueous Solution: An Interesting Contrast. International Journal of Radiation Biology 59:5, pages 1081-1100.
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Articles from other publishers (42)

Jean Cadet, J. Richard Wagner & Dimitar Angelov. (2018) Biphotonic Ionization of DNA : From Model Studies to Cell . Photochemistry and Photobiology 95:1, pages 59-72.
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Huabing Sun, Marisa L. Taverna Porro & Marc M. Greenberg. (2017) Independent Generation and Reactivity of Thymidine Radical Cations. The Journal of Organic Chemistry 82:20, pages 11072-11083.
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Jan Zálešák, Jean-François Constant & Muriel Jourdan. (2016) Nuclear Magnetic Resonance Solution Structure of DNA Featuring Clustered 2′-Deoxyribonolactone and 8-Oxoguanine Lesions. Biochemistry 55:28, pages 3899-3906.
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Marc M. Greenberg. 2016. 119 202 .
Brian R. Berquist & David M. WilsonIIIIII. (2012) Pathways for repairing and tolerating the spectrum of oxidative DNA lesions. Cancer Letters 327:1-2, pages 61-72.
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Francois Samson-Thibault, Guru S. Madugundu, Shanshan Gao, Jean Cadet & J. Richard Wagner. (2012) Profiling Cytosine Oxidation in DNA by LC-MS/MS. Chemical Research in Toxicology 25:9, pages 1902-1911.
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Jean Cadet, Thierry Douki, Didier Gasparutto, Jean‐Luc Ravanat & J.  Richard Wagner. 2012. Encyclopedia of Radicals in Chemistry, Biology and Materials. Encyclopedia of Radicals in Chemistry, Biology and Materials.
Kiran K. K. Sharma, Rahul Tyagi, Shubhadeep Purkayastha & William A. Bernhard. (2010) One-Electron Oxidation of DNA by Ionizing Radiation: Competition between Base-to-Base Hole-Transfer and Hole-Trapping. The Journal of Physical Chemistry B 114:22, pages 7672-7680.
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J. Richard Wagner & Jean Cadet. (2010) Oxidation Reactions of Cytosine DNA Components by Hydroxyl Radical and One-Electron Oxidants in Aerated Aqueous Solutions. Accounts of Chemical Research 43:4, pages 564-571.
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Jean Cadet, Thierry Douki, Didier Gasparutto, Jean‐Luc Ravanat & J. Richard Wagner. 2009. Radical and Radical Ion Reactivity in Nucleic Acid Chemistry. Radical and Radical Ion Reactivity in Nucleic Acid Chemistry 69 97 .
Adity Bose & Samita Basu. (2009) Medium-dependent interactions of quinones with cytosine and cytidine: A laser flash photolysis study with magnetic field effect. Biophysical Chemistry 140:1-3, pages 62-68.
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Vanessa Labet, André Grand, Jean Cadet & Leif A. Eriksson. (2008) Deamination of the Radical Cation of the Base Moiety of 2′-Deoxycytidine: A Theoretical Study. ChemPhysChem 9:8, pages 1195-1203.
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Mayuko Mori, Takeo Ito, Mitsunobu Kawano, Yukinari Takao, Hiroshi Hatta & Sei-ichi Nishimoto. (2008) Generation of Thymine Radicals from 6-Alkoxy-5-bromo-5,6-dihydrothymine Derivatives by Radiolytic Reduction and Photolytic Dehalogenation. Chemical Research in Toxicology 21:4, pages 958-965.
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Thierry Douki. 2007. Biophysical and Physiological Effects of Solar Radiation on Human Skin. Biophysical and Physiological Effects of Solar Radiation on Human Skin 227 269 .
Clemens von Sonntag. 2006. Free-Radical-Induced DNA Damage and Its Repair. Free-Radical-Induced DNA Damage and Its Repair 211 334 .
Marina Roginskaya, Yuriy Razskazovskiy & William A. Bernhard. (2005) 2-Deoxyribonolactone Lesions in X-ray-Irradiated DNA: Quantitative Determination by Catalytic 5-Methylene-2-furanone Release. Angewandte Chemie International Edition 44:38, pages 6210-6213.
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Marina Roginskaya, Yuriy Razskazovskiy & William A. Bernhard. (2005) 2-Deoxyribonolactone Lesions in X-ray-Irradiated DNA: Quantitative Determination by Catalytic 5-Methylene-2-furanone Release. Angewandte Chemie 117:38, pages 6366-6369.
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Zhenjiu Liu, Yuan Gao, Yu Zeng, Fang Fang, Dahn Chi & Yinsheng Wang. (2007) Isolation and Characterization of a Novel Cross-link Lesion in d(CpC) Induced by One-electron Photooxidation¶. Photochemistry and Photobiology 80:2, pages 209-215.
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Zhenjiu Liu, Yuan Gao, Yu Zeng, Fang Fang, Dahn Chi & Yinsheng Wang. (2004) Isolation and Characterization of a Novel Cross-link Lesion in d(CpC) Induced by One-electron Photooxidation¶. Photochemistry and Photobiology 80:2, pages 209.
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Thierry Douki, Jean-Luc Ravanat, Dimitar Angelov, J. Richard Wagner & Jean Cadet. 2004. Longe-Range Charge Transfer in DNA I. Longe-Range Charge Transfer in DNA I 1 25 .
Jean Cadet, Thierry Douki & Jean-Luc Ravanat. 2003. Redox-Genome Interactions in Health and Disease. Redox-Genome Interactions in Health and Disease.
T. L. Luke, H. Mohan, V. M. Manoj, P. Manoj, J. P. Mittal & C. T. Aravindakumar. (2003) Reaction of sulphate radical anion (SO. 4 -) with hydroxy-and methyl-substituted pyrimidines: a pulse radiolysis study. Research on Chemical Intermediates 29:4, pages 379-391.
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C. von Sonntag & H.-P. Schuchmann. 2001. Radiation Chemistry - Present Status and Future Trends. Radiation Chemistry - Present Status and Future Trends 513 551 .
Mitsuharu Kotera, Yoann Roupioz, Eric Defrancq, Anne-Gaëlle Bourdat, Julian Garcia, Christian Coulombeau & Jean Lhomme. (2000) The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion. Chemistry 6:22, pages 4163-4169.
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Lucienne Voituriez & Jean Cadet. (2008) Isolation and Characterization of Two Furan‐side Photoadducts of 7‐Methylpyrido[3,4‐c] Psoralen to the Sugar Moiety of 2‐Deoxyadenosine†. Photochemistry and Photobiology 70:2, pages 152-158.
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Jae-Taeg Hwang & Marc M. Greenberg. (1999) Kinetics and Stereoselectivity of Thiol Trapping of Deoxyuridin-1‘-yl in Biopolymers and Their Relationship to the Formation of Premutagenic α-Deoxynucleotides. Journal of the American Chemical Society 121:18, pages 4311-4315.
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Marc M. Greenberg. 1999. Comprehensive Natural Products Chemistry. Comprehensive Natural Products Chemistry 371 425 .
Mitsuharu Kotera, Anne-Gaelle Bourdat, Eric Defrancq & Jean Lhomme. (1998) A Highly Efficient Synthesis of Oligodeoxyribonucleotides Containing the 2‘-Deoxyribonolactone Lesion. Journal of the American Chemical Society 120:45, pages 11810-11811.
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Tongqian Chen & Marc M. Greenberg. (1998) Model Studies Indicate That Copper Phenanthroline Induces Direct Strand Breaks via β-Elimination of the 2‘-Deoxyribonolactone Intermediate Observed in Enediyne Mediated DNA Damage. Journal of the American Chemical Society 120:15, pages 3815-3816.
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J. Cadet, M. Berger, T. Douki & J. -L. Ravanat. 1997. Reviews of Physiology Biochemistry and Pharmacology, Volume 131. Reviews of Physiology Biochemistry and Pharmacology, Volume 131 1 87 .
T. MelvinS. W. BotchwayA. W. ParkerP. O'Neill. (1996) Induction of Strand Breaks in Single-Stranded Polyribonucleotides and DNA by Photoionization:  One Electron Oxidized Nucleobase Radicals as Precursors. Journal of the American Chemical Society 118:42, pages 10031-10036.
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J. Cadet, M. Berger, B. Morin, S. Raoul & J. R. Wagner. 1995. Analysis of Free Radicals in Biological Systems. Analysis of Free Radicals in Biological Systems 51 64 .
Helmut Görner. (1994) New trends in photobiology. Journal of Photochemistry and Photobiology B: Biology 26:2, pages 117-139.
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Helmut Görner & Gagik G. Gurzadyan. (1993) Photolysis of polycytidylic acid on 193 nm laser excitation. Journal of Photochemistry and Photobiology A: Chemistry 71:2, pages 155-160.
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David Becker & Michael D. Sevilla. 1993. Advances in Radiation Biology - DNA and Chromatin Damage Caused by Radiation. Advances in Radiation Biology - DNA and Chromatin Damage Caused by Radiation 121 180 .
Gagik G. Gurzadyan & Helmut Gorner. (1992) BASE RELEASE FROM DNA AND POLYNUCLEOTIDES UPON 193 nm LASER EXCITATION. Photochemistry and Photobiology 56:3, pages 371-378.
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Helmut Görner. (1991) Chromophore loss of uracil derivatives and polyuridylic acid in aqueous solution caused by 248 nm laser pulses and continuous UV irradiation: Mechanism of the photohydration of pyrimidines. Journal of Photochemistry and Photobiology B: Biology 10:1-2, pages 91-110.
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D. Angelov, M. Berger, J. Cadet, N. Getoff, E. Keskinova & S. Solar. (1991) Comparison of the effects of high-power U.V.-laser pulses and ionizing radiation on nucleic acids and related compounds. International Journal of Radiation Applications and Instrumentation. Part C. Radiation Physics and Chemistry 37:5-6, pages 717-727.
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Clemens von Sonntag. 1991. Physical and Chemical Mechanisms in Molecular Radiation Biology. Physical and Chemical Mechanisms in Molecular Radiation Biology 287 321 .
Jean Cadet, Maurice Berger, Prakash C. Joshi, Anthony Shaw, Lucienne Voituriez, Lou-Sing Kan & Richard Wagner. 1991. Photobiology. Photobiology 49 59 .
J. R. Wagner, J- E. van Lier & L. J. JOHNSTON. (1990) QUINONE SENSITIZED ELECTRON TRANSFER PHOTOOXIDATION OF NUCLEIC ACIDS: CHEMISTRY OF THYMINE AND THYMIDINE RADICAL CATIONS IN AQUEOUS SOLUTION. Photochemistry and Photobiology 52:2, pages 333-343.
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J.R. Wagner, J.E. Van Lier, C. Decarroz, M. Berger & J. Cadet. 1990. Oxygen Radicals in Biological Systems Part B: Oxygen Radicals and Antioxidants. Oxygen Radicals in Biological Systems Part B: Oxygen Radicals and Antioxidants 502 511 .

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