Formation of 2′-deoxyuridine hydrates upon exposure of nucleosides to gamma radiation and UVC-irradiation of isolated and cellular DNA
Abstract
The two diastereoisomers of 6-hydroxy-5,6-dihydro-2'-deoxyuridine (dUrd hydrates) are produced upon deamination of the related 2'-deoxycytidine derivatives. Liquid chromatography coupled to tandem mass spectrometry was used to quantify dUrd hydrates. Their rate constant of formation within UVC-irradiated solutions of dCyd was first determined. Their formation was also shown to occur within solutions of either dUrd or dCyd exposed to gamma-rays in the absence of oxygen. dUrd hydrates were then quantified within isolated and cellular DNA exposed to UVC light. In both cases, their yield of formation was found to be, at least, 2 orders of magnitude lower than the overall yield of bipyrimidine photoproducts such as cyclobutane dimers and (6-4) photoproducts.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Cytosine hydrates and adenine-containing dimers have been isolated in model systems, but their yields are about two orders of magnitude lower than bipyrimidine photoproducts in double-stranded DNA.
“Other photoproducts such as cytosine hydrates (41,42) or adenine-containing dimers (43,44) have been isolated in model systems but their yields are 2 orders of magnitude lower than that of bipyrimidine photoproducts in double-stranded (ds) DNA.”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [42]
Cites
Wavelength dependence of oxidative DNA damage induced by UV and visible light
Kielbassa, C. (1997) · Carcinogenesis · doi:10.1093/carcin/18.4.811 · Cited by 616 · see citing works
Douki, T., & Cadet, J. (2001) · Biochemistry · doi:10.1021/bi0022543 · Cited by 337 · see citing works
Self-citationTruscott, T. G. (1991) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/1010-6030(91)87077-9 · Cited by 310 · see citing works
Pouget, J.-P., Douki, T., Richard, M.-J., & Cadet, J. (2000) · Chemical Research in Toxicology · doi:10.1021/tx000020e · Cited by 274 · see citing works
Self-citationDouki, T., Court, M., Sauvaigo, S., Odin, F., & Cadet, J. (2000) · Journal of Biological Chemistry · doi:10.1074/jbc.275.16.11678 · Cited by 239 · see citing works
Self-citationMitchell, D. L., Jen, J., & Cleaver, J. E. (1991) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1991.tb02084.x · Cited by 123 · see citing works
Mechanism of action of a mammalian DNA repair endonuclease
Doetsch, P. W., Helland, D. E., & Haseltine, W. A. (1986) · Biochemistry · doi:10.1021/bi00356a054 · Cited by 120 · see citing works
Boorstein, R. J., Hilbert, T. P., Cadet, J., Cunningham, R. P., & Teebor, G. W. (1989) · Biochemistry · doi:10.1021/bi00441a007 · Cited by 108 · see citing works
Self-citationHilbert, T. P., Boorstein, R. J., Kung, H. C., Bolton, P. H., Xing, D., Cunningham, R. P., & Teebor, G. W. (1996) · Biochemistry · doi:10.1021/bi952516e · Cited by 80 · see citing works
Formation and stability of repairable pyrimidine photohydrates in DNA
Boorstein, R. J., Hilbert, T. P., Cunningham, R. P., & Teebor, G. W. (1990) · Biochemistry · doi:10.1021/bi00498a004 · Cited by 77 · see citing works
Moore, A. M. (1958) · Canadian Journal of Chemistry · doi:10.1139/v58-038 · Cited by 62 · see citing works
Photochemistry of cytosine nucleosides and nucleotides
Wierzchowski, K. L., & Shugar, D. (1957) · Biochimica et Biophysica Acta · doi:10.1016/0006-3002(57)90479-1 · Cited by 59 · see citing works
Peroxydes formés par action du rayonnement γ sur la thymine en solution aqueuse aérée
Cadet, J., & Teoule, R. (1971) · Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis · doi:10.1016/0005-2787(71)90004-9 · Cited by 49 · see citing works
Self-citation(1961) · PubMed · Cited by 44 · see citing works
Evidence for the presence of cytosine photohydrates in UV irradiated nucleic acids
Grossman, L. I., & Rodgers, E. (1968) · Biochemical and Biophysical Research Communications · doi:10.1016/0006-291x(68)90409-9 · Cited by 39 · see citing works
O6,5'-Cyclo-5,6-dihydro-2'-deoxyuridine. Novel deoxyuridine photoproducts
Cadet, J., Kan, L., & Wang, S. Y. (1978) · Journal of the American Chemical Society · doi:10.1021/ja00489a027 · Cited by 37 · see citing works
Self-citationReversal mechanisms for the photohydrates of cytosine and its derivatives
Deboer, G., Klinghoffer, O., & Johns, H. E. (1970) · Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis · doi:10.1016/0005-2787(70)90033-x · Cited by 32 · see citing works
Haysom, H. R., Phillips, J. M., & SCHOLES, G. (1972) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39720001082 · Cited by 26 · see citing works
Teoule, R., Bonicel, A., Bert, C., & Fouqué, B. (1978) · Journal of the American Chemical Society · doi:10.1021/ja00489a034 · Cited by 25 · see citing works
Jen, J., Mitchell, D. L., Cunningham, R. P., Smith, C. A., Taylor, J., & Cleaver, J. E. (1997) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1997.tb08565.x · Cited by 23 · see citing works
Degradation Radio-induite de la Thymidine en Solution Aqueuse Désaérée
Cadet, J., Balland, A., & Berger, M. (1981) · International Journal of Radiation Biology and Related Studies in Physics Chemistry and Medicine · doi:10.1080/09553008114550141 · Cited by 22 · see citing works
Self-citationDouki, T., & Cadet, J. (1995) · Birkhäuser Basel eBooks · doi:10.1007/978-3-0348-9061-8_9 · Cited by 20 · see citing works
Self-citationEffect of pH and Temperature on the Stability of UV-Induced Repairable Pyrimidine Hydrates in DNA
O'Donnell, R. E., Boorstein, R. J., Cunningham, R. P., & Teebor, G. W. (1994) · Biochemistry · doi:10.1021/bi00199a008 · Cited by 18 · see citing works
Direct measurement of pyrimidine C6-hydrate stability
Carter, K. N. (2001) · Bioorganic & Medicinal Chemistry · doi:10.1016/s0968-0896(01)00137-7 · Cited by 9 · see citing works
Examination of the photokinetics of 1-beta-D-arabinofuranosylcytosine and deoxyribocytidine.
Schott, H. N., Hommel, U., & Gauglitz, G. (1988) · PubMed · Cited by 8 · see citing works
Cadet, J., & Teoule, R. (1975) · Journal of Chromatography A · doi:10.1016/s0021-9673(00)89031-7 · Cited by 7 · see citing works
Self-citationProperties of diastereoisomeric photohydrates of uracil nucleosides.
Pietrzykowska, I., & Shugar, D. (1974) · PubMed · Cited by 5 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Ultraviolet radiation-mediated damage to cellular DNA
Cadet, J., Sage, E., & Douki, T. (2005) · Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis · doi:10.1016/j.mrfmmm.2004.09.012 · Cited by 932 · see citing works
Self-citationDNA Base Damage by Reactive Oxygen Species, Oxidizing Agents, and UV Radiation
Cadet, J., & Wagner, J. R. (2013) · Cold Spring Harbor Perspectives in Biology · doi:10.1101/cshperspect.a012559 · Cited by 903 · see citing works
Self-citationCadet, J., Douki, T., & Ravanat, J. (2015) · Photochemistry and Photobiology · doi:10.1111/php.12368 · Cited by 355 · see citing works
Self-citationPhotoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup>
Cadet, J., Mouret, S., Ravanat, J., & Douki, T. (2012) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2012.01200.x · Cited by 300 · see citing works
Self-citationActions of ultraviolet light on cellular structures
Pattison, D. I., & Davies, M. J. (2006) · Experientia Supplementum · doi:10.1007/3-7643-7378-4_6 · Cited by 283 · see citing works
Douki, T. (2013) · Photochemical & Photobiological Sciences · doi:10.1039/c3pp25451h · Cited by 132 · see citing works
Self-citationSolar UV Radiation-Induced DNA Bipyrimidine Photoproducts: Formation and Mechanistic Insights
Cadet, J., Grand, A., & Douki, T. (2014) · Topics in current chemistry · doi:10.1007/128_2014_553 · Cited by 130 · see citing works
Self-citationInter-strand photoproducts are produced in high yield within A-DNA exposed to UVC radiation
Douki, T. (2003) · Nucleic Acids Research · doi:10.1093/nar/gkg408 · Cited by 96 · see citing works
Self-citationKundu, L. M., Linne, U., Marahiel, M. A., & Carell, T. (2004) · Chemistry - A European Journal · doi:10.1002/chem.200305731 · Cited by 88 · see citing works
Spore Photoproduct: A Key to Bacterial Eternal Life
Desnous, C., Guillaume, D. M., & Clivio, P. (2009) · Chemical Reviews · doi:10.1021/cr0781972 · Cited by 74 · see citing works
Physiological Aspects of UV-Excitation of DNA
RICHA, R., Sinha, R. P., & Häder, D. (2014) · Topics in current chemistry · doi:10.1007/128_2014_531 · Cited by 64 · see citing works
Detecting UV-induced nucleic-acid damage
El-Yazbi, A. F., & Loppnow, G. R. (2014) · TrAC Trends in Analytical Chemistry · doi:10.1016/j.trac.2014.05.010 · Cited by 43 · see citing works
Contribution of oxidation reactions to photo‐induced damage to cellular DNA
Cadet, J., Angelov, D., Mascio, P. D., & Wagner, J. R. (2024) · Photochemistry and Photobiology · doi:10.1111/php.13990 · Cited by 27 · see citing works
Self-citationHydrolytic Deamination of 5,6-Dihydrocytosine in a Protic Medium: A Theoretical Study
Labet, V., Morell, C., Douki, T., Cadet, J., Eriksson, L. A., & Grand, A. (2010) · The Journal of Physical Chemistry A · doi:10.1021/jp9049044 · Cited by 26 · see citing works
Self-citationThe Photophysics of Nucleic Acids: Consequences for the Emergence of Life
Kufner, C. L., Bucher, D., & Sasselov, D. D. (2022) · ChemSystemsChem · doi:10.1002/syst.202200019 · Cited by 19 · see citing works
Grand, A., Cadet, J., Eriksson, L. A., Labet, V., Jorge, N. L., Schreiber, M. L., Douki, T., & Morell, C. (2012) · Highlights in theoretical chemistry · doi:10.1007/978-3-642-34462-6_31 · Cited by 11 · see citing works
Self-citationShetlar, M. D., & Chung, J. (2011) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2011.00936.x · Cited by 6 · see citing works
Shetlar, M. D., Hom, K., & Venditto, V. J. (2013) · Photochemistry and Photobiology · doi:10.1111/php.12069 · Cited by 6 · see citing works
N4‐Methylation of Cytosine Drastically Favors the Formation of (6‐4) Photoproducts in a TCG Context
Douki, T., Meador, J. A., Bérard, I., & Wack, A. (2014) · Photochemistry and Photobiology · doi:10.1111/php.12365 · Cited by 6 · see citing works
Self-citationDouki, T. (2007) · Royal Society of Chemistry eBooks · doi:10.1039/9781847557957-00225 · Cited by 3 · see citing works
Self-citationThe remarkable UV light invulnerability of thymine GNA dinucleotides
Castex, S., Martinez, A., Harakat, D., Guillaume, D. M., & Clivio, P. (2019) · Chemical Communications · doi:10.1039/c9cc04355a · Cited by 3 · see citing works
Kundu, L. M. (2005) · Electronic Theses of LMU Munich (Ludwig-Maximilians-Universität München) · doi:10.5282/edoc.3195 · Cited by 2 · see citing works
- Authors
- Douki, T., Vadesne-Bauer, G., & Cadet, J.
- Affiliations
- Commissariat à l'Énergie Atomique et aux Énergies Alternatives (FR)
- Corresponding author
- Douki, Thierry
- Cadet, Jean
- Venue
- Photochemical & Photobiological Sciences
- Published
- 2002-06-13
- Volume
- 1
- Issue
- 8
- Pages
- 565-569
- ISSN
- 1474-905X (ISSN-L)
- 1474-9092
- OpenAlex
- W1977709378
- Cited by
- 22
- References
- 27
- Citations by year
- 2024: 1 · 2022: 1 · 2019: 1 · 2014: 5 · 2013: 3 · 2012: 2
- FWCI
- 0.46
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Photochemical & Photobiological Sciences (publishedVersion)
- PubMed (publishedVersion)
- HAL (submittedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Carcinogens and Genotoxicity Assessment
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA Repair Mechanisms
- Keywords
- diastereomers, 2'-deoxycytidine, deamination, gamma radiation, UV-C irradiation, DNA damage, cyclobutane dimers, 6-4 photoproducts, radiation chemistry, DNA adducts
- MeSH terms
- Animals, Cattle, Chromatography, High Pressure Liquid, Deoxyuridine, DNA, Gamma Rays, Nucleosides, Mass Spectrometry, Ultraviolet Rays, Water
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review