Singlet Oxygen Oxidation of Isolated and Cellular DNA: Product Formation and Mechanistic Insights
Abstract
This survey focuses on recent aspects of the singlet oxygen oxidation of the guanine moiety of nucleosides, oligonucleotides, isolated and cellular DNA that has been shown to be the exclusive DNA target for this biologically relevant photo‐generated oxidant. A large body of mechanistic data is now available from studies performed on nucleosides in both aprotic solvents and aqueous solutions. A common process to both reaction conditions is the formation of 8‐oxo‐7,8‐dihydroguanine by reduction of 8‐hydroperoxyguanine that arises from the rearrangement of initially formed endoperoxide across the 4,8‐bond of the purine moiety. However, in organic solvent the hydroperoxide is converted as a major degradation pathway into a dioxirane that subsequently decomposes into a complex pattern of oxidation products. A different reaction that involved the formation of a highly reactive quinonoid intermediate consecutively to the loss of a water molecule from the 8‐hydroperoxide has been shown to occur in aqueous solution. Subsequent addition of a water molecule at C5 leads to the generation of a spiroiminodihydantoin compound via a rearrangement that involves an acyl shift. However, in both isolated and cellular DNA the latter decomposition pathway is at the best a minor process, because only 8‐oxo‐7,8‐dihydroguanine has been found to be generated. It is interesting to point out that singlet oxygen has been shown to contribute predominantly to the formation of 8‐oxo‐7,8‐dihydroguanine in the DNA of bacterial and human cells upon exposure to UVA radiation. It may be added that the formation of secondary singlet‐oxygen oxidation products of 8‐oxo‐7,8‐dihydroguanine, including spiroiminodihydantoin and oxaluric acid that were characterized in nucleosides and oligonucleotide, respectively, have not yet been found in cellular DNA.
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The endoperoxide intermediate rearranges quantitatively within double-stranded DNA into 8-hydroxyperoxyguanine, which is further reduced to 8-oxoGua, the exclusive singlet oxygen oxidation product.
“The latter intermediate quantitatively rearranges within ds DNA into 8-hydroxyperoxyguanine (39,99) that is further reduced into 8-oxoGua (Fig. 5), the exclusive 1 O 2 oxidation product (39,100,101).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [39]
Cites
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-citationPhotosensitized Oxidation and Singlet Oxygen: Consequences in Biological Systems
Foote, C. S. (1976) · Elsevier eBooks · doi:10.1016/b978-0-12-566502-5.50010-x · Cited by 824 · see citing works
Oxidative damage to DNA: formation, measurement and biochemical features
Cadet, J., Douki, T., Gasparutto, D., & Ravanat, J. (2003) · Mutation research. Fundamental and molecular mechanisms of mutagenesis · doi:10.1016/j.mrfmmm.2003.09.001 · Cited by 727 · see citing works
Self-citationWavelength 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
Boiteux, S., Gajewski, E., Laval, J., & Dizdaroğlu, M. (1992) · Biochemistry · doi:10.1021/bi00116a016 · Cited by 594 · see citing works
Agar, N., Halliday, G. M., Barnetson, R. S., Ananthaswamy, H. N., Wheeler, M., & Jones, A. M. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0401141101 · Cited by 530 · see citing works
Mechanisms of formation, genotoxicity, and mutation of guanine oxidation products
Neeley, W. L., & Essigmann, J. M. (2006) · Chemical Research in Toxicology · doi:10.1021/tx0600043 · Cited by 510 · see citing works
Induction of oxidative DNA base damage in human skin cells by UV and near visible radiation
Kvam, E. (1997) · Carcinogenesis · doi:10.1093/carcin/18.12.2379 · Cited by 344 · see citing works
Singlet Oxygen Induces Oxidation of Cellular DNA
Ravanat, J., Mascio, P. D., Martinez, G. R., de Medeiros, M. H. G., & Cadet, J. (2000) · Journal of Biological Chemistry · doi:10.1074/jbc.m006681200 · Cited by 327 · see citing works
Self-citationSinglet-Oxygen Chemiluminescence in Peroxide Reactions
Adam, W., Kazakov, D. V., & Kazakov, V. P. (2005) · Chemical Reviews · doi:10.1021/cr0300035 · Cited by 315 · see citing works
Ravanat, J. (2002) · Carcinogenesis · doi:10.1093/carcin/23.11.1911 · Cited by 310 · see citing works
Self-citationLee, P. C. C., & Rodgers, M. A. J. (1987) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1987.tb08407.x · Cited by 274 · 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-citationFrelon, S., Douki, T., Ravanat, J.-L., Pouget, J.-P., Tornabene, C., & Cadet, J. (2000) · Chemical Research in Toxicology · doi:10.1021/tx000085h · Cited by 271 · see citing works
Self-citationSteinbeck, M. J., Khan, A. U., & Karnovsky, M. J. (1992) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)42228-4 · Cited by 258 · see citing works
Luo, W., Muller, J. G., Rachlin, E. M., & Burrows, C. J. (2000) · Organic Letters · doi:10.1021/ol9913643 · Cited by 242 · see citing works
Miyamoto, S., Martinez, G. R., de Medeiros, M. H. G., & Mascio, P. D. (2003) · Journal of the American Chemical Society · doi:10.1021/ja029115o · Cited by 240 · see citing works
Self-citationOxidative and alkylating damage in DNA
Martinez, G. R. (2003) · Mutation Research/Reviews in Mutation Research · doi:10.1016/j.mrrev.2003.05.005 · Cited by 230 · see citing works
Self-citationPhotodynamic therapy in oncology
Kinsella, T. J., Colussi, V., Oleinick, N. L., & Sibata, C. H. (2001) · Expert Opinion on Pharmacotherapy · doi:10.1517/14656566.2.6.917 · Cited by 212 · see citing works
Luo, W., Muller, J. G., Rachlin, E. M., & Burrows, C. J. (2001) · Chemical Research in Toxicology · doi:10.1021/tx010072j · Cited by 201 · see citing works
Ravanat, J., & Cadet, J. (1995) · Chemical Research in Toxicology · doi:10.1021/tx00045a009 · Cited by 180 · see citing works
Self-citationYe, Y., Muller, J. G., Luo, W., Mayne, C. L., Shallop, A. J., Jones, R. A., & Burrows, C. J. (2003) · Journal of the American Chemical Society · doi:10.1021/ja0378660 · Cited by 168 · see citing works
Besaratinia, A., Synold, T. W., Chen, H.-H., Chang, C., Xi, B., Riggs, A. D., & Pfeifer, G. P. (2005) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0502311102 · Cited by 156 · see citing works
Miyamoto, S., Martinez, G. R., Martins, A. P. B., de Medeiros, M. H. G., & Mascio, P. D. (2003) · Journal of the American Chemical Society · doi:10.1021/ja029262m · Cited by 155 · see citing works
Self-citationKozmin, S., Slezak, G., Reynaud-Angelin, A., Elie, C., de Rycke, Y., Boiteux, S., & Sage, E. (2005) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0504497102 · Cited by 148 · see citing works
Courdavault, S., Baudouin, C., Charveron, M., Favier, A., Cadet, J., & Douki, T. (2004) · Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis · doi:10.1016/j.mrfmmm.2004.07.011 · Cited by 145 · see citing works
Self-citationNiles, J. C., Wishnok, J. S., & Tannenbaum, S. R. (2001) · Organic Letters · doi:10.1021/ol006993n · Cited by 142 · see citing works
Duarte, V., Gasparutto, D., Yamaguchi, L. F., Ravanat, J., Martinez, G. R., de Medeiros, M. H. G., Mascio, P. D., & Cadet, J. (2000) · Journal of the American Chemical Society · doi:10.1021/ja002218r · Cited by 138 · see citing works
Self-citationMiyamoto, S., Martinez, G. R., Rettori, D., Augusto, O., Medeiros, M. H. G., & Di Mascio, P. (2006) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0508170103 · Cited by 137 · see citing works
Self-citationLuo, W., Muller, J. G., & Burrows, C. J. (2001) · Organic Letters · doi:10.1021/ol0161763 · Cited by 135 · see citing works
Oxidation of Guanine in Cellular DNA by Solar UV Radiation: Biological Role†
Douki, T., Perdiz, D., Grof, P., Kuluncsics, Z., Moustacchi, E., Cadet, J., & Sage, E. (1999) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1999.tb07988.x · Cited by 133 · see citing works
Self-citationZhang, X., Rosenstein, B. S., Wang, Y., Lebwohl, M., Mitchell, D. M., & Wei, H. (1997) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1997.tb01886.x · Cited by 129 · see citing works
Raoul, S., & Cadet, J. (1996) · Journal of the American Chemical Society · doi:10.1021/ja952347l · Cited by 124 · see citing works
Self-citationBiophysical Aspects of Photodynamic Therapy
Juzeniene, A., Nielsen, K. P., & Moan, J. E. (2006) · Journal of Environmental Pathology Toxicology and Oncology · doi:10.1615/jenvironpatholtoxicoloncol.v25.i1-2.20 · Cited by 123 · see citing works
Pflaum, M., Kielbassa, C., Garmyn, M., & Epe, B. (1998) · Mutation Research/DNA Repair · doi:10.1016/s0921-8777(98)00029-9 · Cited by 122 · see citing works
Subcellular, Time-Resolved Studies of Singlet Oxygen in Single Cells
Snyder, J. W., Skovsen, E., Lambert, J. D. C., & Ogilby, P. R. (2005) · Journal of the American Chemical Society · doi:10.1021/ja055342p · Cited by 115 · see citing works
Endoperoxide formation in a guanosine derivative
Sheu, C., & Foote, C. S. (1993) · Journal of the American Chemical Society · doi:10.1021/ja00075a105 · Cited by 111 · see citing works
Martinez, G. R., Ravanat, J., de Medeiros, M. H. G., Cadet, J., & Mascio, P. D. (2000) · Journal of the American Chemical Society · doi:10.1021/ja0016452 · Cited by 111 · see citing works
Self-citationSheu, C., & Foote, C. S. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00129a004 · Cited by 107 · see citing works
[14] Singlet oxygen DNA damage products: Formation and measurement
Cadet, J., Douki, T., Pouget, J., & Ravanat, J. (2000) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/s0076-6879(00)19016-0 · Cited by 92 · see citing works
Self-citationPHTHALOCYANINE AND NAPHTHALOCYANINE PHOTOSENSITIZED OXIDATION OF 2′‐DEOXYGUANOSINE
Ravanat, J., Berger, M., Bénard, F., Langlois, R., Ouellet, R., van Lier, J. E., & Cadet, J. (1992) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1992.tb08528.x · Cited by 90 · see citing works
Self-citationSheu, C., & Foote, C. S. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00106a054 · Cited by 86 · see citing works
Ravanat, J., Sauvaigo, S., Caillat, S., Martinez, G. R., de Medeiros, M. H. G., Mascio, P. D., Favier, A. E., & Cadet, J. (2004) · Biological Chemistry · doi:10.1515/bc.2004.003 · Cited by 84 · see citing works
Self-citationNia, A. B., Synold, T. W., Xi, B., & Pfeifer, G. P. (2004) · Biochemistry · doi:10.1021/bi049761v · Cited by 83 · see citing works
McCallum, J. E. B., Kuniyoshi, C. Y., & Foote, C. S. (2004) · Journal of the American Chemical Society · doi:10.1021/ja030678p · Cited by 83 · see citing works
Mechanistic aspects of the oxidation of DNA constituents mediated by singlet molecular oxygen
Ravanat, J., Martinez, G. R., de Medeiros, M. H. G., Mascio, P. D., & Cadet, J. (2003) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2003.10.018 · Cited by 82 · see citing works
Self-citationThe Insulated SolarFenton Hybrid Process: Fundamental Investigations
Sagawe, G., Lehnard, A., Lübber, M., & Bahnemann, D. W. (2001) · Helvetica Chimica Acta · doi:10.1002/1522-2675(20011219)84:12 · Cited by 78 · see citing works
Self-citationSheu, C., Kang, P., Khan, S., & Foote, C. S. (2002) · Journal of the American Chemical Society · doi:10.1021/ja011696e · Cited by 78 · see citing works
Kang, P., & Foote, C. S. (2002) · Journal of the American Chemical Society · doi:10.1021/ja012038x · Cited by 77 · see citing works
Martinez, G. R., de Medeiros, M. H. G., Ravanat, J., Cadet, J., & Mascio, P. D. (2002) · Biological Chemistry · doi:10.1515/bc.2002.063 · Cited by 74 · see citing works
Self-citationAdam, W., Arnold, M. A., Grüne, M., Nau, W. M., Pischel, U., & Saha‐Möller, C. R. (2002) · Organic Letters · doi:10.1021/ol017138m · Cited by 68 · see citing works
Physiological production of singlet molecular oxygen in the myeloperoxidase‐H2O2‐chloride system
Kiryu, C., Makiuchi, M., Miyazaki, J., FUJINAGA, T., & Kakinuma, K. (1999) · FEBS Letters · doi:10.1016/s0014-5793(98)01700-1 · Cited by 68 · see citing works
Rosen, J. E., Prahalad, A. K., & Williams, G. M. (1996) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1996.tb02430.x · Cited by 68 · see citing works
Photosensitized Oxidation of 13C,15N-Labeled Imidazole Derivatives
Kang, P., & Foote, C. S. (2002) · Journal of the American Chemical Society · doi:10.1021/ja012253d · Cited by 64 · see citing works
UVB and UVA radiation-mediated damage to isolated and cellular DNA
Cadet, J., Courdavault, S., Ravanat, J., & Douki, T. (2005) · Pure and Applied Chemistry · doi:10.1351/pac200577060947 · Cited by 63 · see citing works
Self-citationMethylene blue-mediated photooxidation of 7,8-dihydro-8-oxo-2′-deoxyguanosine
Buchko, G. W., Wagner, J. R., Cadet, J., Raoul, S., & Weinfeld, M. (1995) · Biochimica et Biophysica Acta (BBA) - Gene Structure and Expression · doi:10.1016/0167-4781(95)00078-u · Cited by 62 · see citing works
Self-citationEffects of Duplex Stability on Charge-Transfer Efficiency within DNA
Douki, T., Ravanat, J., Angelov, D., Wagner, J. R., & Cadet, J. (2012) · Topics in current chemistry · doi:10.1007/b94409 · Cited by 57 · see citing works
Self-citationPHOTOCHEMISTRY OF NUCLEIC ACIDS
Hélène, C. (1973) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1973.tb06462.x · Cited by 54 · see citing works
Fischer‐Nielsen, A., Loft, S. H., & Jensen, K. G. (1993) · Carcinogenesis · doi:10.1093/carcin/14.11.2431 · Cited by 52 · see citing works
Prat, F., Hou, C.-C., & Foote, C. S. (1997) · Journal of the American Chemical Society · doi:10.1021/ja963537e · Cited by 51 · see citing works
Tatsuzawa, H., Maruyama, T., Hori, K., Sano, Y., & Nakano, M. (1999) · Biochemical and Biophysical Research Communications · doi:10.1006/bbrc.1999.1265 · Cited by 47 · see citing works
Structural and Thermodynamic Features of Spiroiminodihydantoin Damaged DNA Duplexes
Jia, L., Shafirovich, V., Shapiro, R., Geacintov, N. E., & Broyde, S. B. (2005) · Biochemistry · doi:10.1021/bi050790v · Cited by 47 · see citing works
Buchko, G. W., Cadet, J., Berger, M., & Ravanat, J. (1992) · Nucleic Acids Research · doi:10.1093/nar/20.18.4847 · Cited by 47 · see citing works
Self-citationChemistry of singlet oxygen. XVI. Long lifetime of singlet oxygen in carbon disulfide
Foote, C. S., Peterson, E. R., & Lee, K. (1972) · Journal of the American Chemical Society · doi:10.1021/ja00758a073 · Cited by 45 · see citing works
Singlet oxygen sensitisation by excited state DNA
Bishop, S. M., Malone, M. E., Phillips, D., Parker, A. W., & Symons, M. C. R. (1994) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39940000871 · Cited by 44 · see citing works
Chworoś, A., Coppel, Y., Dubey, I. Y., Pratviel, G., & Meunier, B. (2001) · Journal of the American Chemical Society · doi:10.1021/ja003945p · Cited by 44 · see citing works
Mohammad, T., & Morrison, H. A. (1996) · Journal of the American Chemical Society · doi:10.1021/ja9519187 · Cited by 39 · see citing works
Jia, L., Shafirovich, V., Shapiro, R., Geacintov, N. E., & Broyde, S. B. (2005) · Biochemistry · doi:10.1021/bi0473657 · Cited by 36 · see citing works
Ravanat, J., Berger, M., Bénard, F., Langlois, R., Ouellet, R., van Lier, J. E., & Cadet, J. (1984) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1984.tb08389.x · Cited by 30 · see citing works
Self-citationCharacterization of the Dehydro-Guanidinohydantoin Oxidation Product of Guanine in a Dinucleotide
Chworoś, A., Seguy, C., Pratviel, G., & Meunier, B. (2002) · Chemical Research in Toxicology · doi:10.1021/tx0200717 · Cited by 29 · see citing works
Photodynamic DNA damage mediated by δ-aminolevulinic acid-induced porphyrins
Duez, P., Hanocq, M., & Dubois, J. (2001) · Carcinogenesis · doi:10.1093/carcin/22.5.771 · Cited by 28 · see citing works
Peroxides in Biological Systems
Cadet, J., & Mascio, P. D. (2009) · Patai's chemistry of functional groups · doi:10.1002/9780470682531.pat0357 · Cited by 27 · see citing works
Self-citationCharacterization of an oxaluric acid derivative as a guanine oxidation product.
Seguy, C., Pratviel, G., & Meunier, B. (2001) · Chemical Communications · doi:10.1039/b106799k · Cited by 17 · see citing works
Avalle, L. B., Dillon, J. P., Tari, S. R., & Gaillard, E. R. (2005) · Photochemistry and Photobiology · doi:10.1562/2005-05-17-rn-531 · Cited by 17 · see citing works
Photooxidation of 2′-Deoxyguanosine 5′-monophosphate in Aqueous Solution ¶
Torun, L., & Morrison, H. A. (2003) · Photochemistry and Photobiology · doi:10.1562/0031-8655(2003)0770370podmia2.0.co2 · Cited by 15 · see citing works
Buchko, G. W., & Cadet, J. (2005) · Photochemistry and Photobiology · doi:10.1562/2005-06-01-ra-562 · Cited by 9 · see citing works
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Sharma, S. K., Mróz, P., Dai, T., Huang, Y., Denis, T. G. S., & Hamblin, M. R. (2012) · Israel Journal of Chemistry · doi:10.1002/ijch.201100062 · Cited by 116 · see citing works
On the in vivo photochemical rate parameters for PDT reactive oxygen species modeling
Kim, M. M., Ghogare, A. A., Greer, A., & Zhu, T. C. (2017) · Physics in Medicine and Biology · doi:10.1088/1361-6560/62/5/r1 · Cited by 102 · see citing works
Samivel, R., Prasad, N. R., & Karthikeyan, S. (2010) · Archives of Dermatological Research · doi:10.1007/s00403-010-1072-1 · Cited by 102 · see citing works
Szokalska, A., Makowski, M., Nowis, D., Wilczynski, G. M., Kujawa, M., Wójcik, C., Młynarczuk-Biały, I., Salwa, P., Bil, J., Janowska, S., et al. (2009) · Cancer Research · doi:10.1158/0008-5472.can-08-3439 · Cited by 102 · see citing works
Zhang (2017) · doi:10.3390/molecules23020228 · Cited by 93 · see citing works
Spencer, W. A., Jeyabalan, J., Kichambre, S., & Gupta, R. C. (2010) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2010.10.693 · Cited by 92 · see citing works
Caminos, D. A., Spesia, M. B., Pons, P., & Durantini, E. N. (2008) · Photochemical & Photobiological Sciences · doi:10.1039/b804965c · Cited by 89 · see citing works
Beltrán-García, M. J., Prado, F. M., Oliveira, M. S., Mendoza, D. O., Scalfo, A. C., Pessoa, A., de Medeiros, M. H. G., White, J. F., & Mascio, P. D. (2014) · PLoS ONE · doi:10.1371/journal.pone.0091616 · Cited by 89 · see citing works
Self-citationTada‐Oikawa, S., Oikawa, S., Hirayama, J., Hirakawa, K., & Kawanishi, S. (2009) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2009.00600.x · Cited by 80 · see citing works
Nia, A. B., Kim, S.-I., & Pfeifer, G. P. (2008) · The FASEB Journal · doi:10.1096/fj.07-105437 · Cited by 78 · see citing works
Hirakawa, K., & Hirano, T. (2007) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2007.00220.x · Cited by 74 · see citing works
Substituent Effects of Porphyrin on Singlet Oxygen Generation Quantum Yields
Nifiatis, F. (2011) · The Open Spectroscopy Journal · doi:10.2174/1874383801105010001 · Cited by 70 · see citing works
Spesia, M. B., Caminos, D. A., Pons, P., & Durantini, E. N. (2009) · Photodiagnosis and Photodynamic Therapy · doi:10.1016/j.pdpdt.2009.01.003 · Cited by 69 · see citing works
Excited singlet molecular O2 (1Δg) is generated enzymatically from excited carbonyls in the dark
Mano, C. M., Prado, F. M., Massari, J., Ronsein, G. E., Martinez, G. R., Miyamoto, S., Cadet, J., Sies, H., de Medeiros, M. H. G., Bechara, E. J. H., et al. (2014) · Scientific Reports · doi:10.1038/srep05938 · Cited by 69 · see citing works
Self-citationFormation of ring-opened and rearranged products of guanine: Mechanisms and biological significance
Jena, N. R., & Mishra, P. C. (2012) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2012.04.008 · Cited by 70 · see citing works
Near-Infrared Fluorescent Biosensors Based on Covalent DNA Anchors
Metternich, J. T., Wartmann, J. A. C., Sistemich, L., Nißler, R., Herbertz, S., & Kruss, S. (2023) · Journal of the American Chemical Society · doi:10.1021/jacs.3c03336 · Cited by 68 · see citing works
Protective mechanisms and responses of micro-fungi towards ultraviolet-induced cellular damage
Wong, H. J., Mohamad‐Fauzi, N., Rizman‐Idid, M., Convey, P., & Alias, S. A. (2018) · Polar Science · doi:10.1016/j.polar.2018.10.001 · Cited by 67 · see citing works
Oxidative modification of cytochrome c by singlet oxygen
Kim, J. H., Rodríguez, M. E., Guo, M. Z., Kenney, M. E., Oleinick, N. L., & Anderson, V. E. (2008) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2007.12.031 · Cited by 65 · see citing works
Sun, H., Wu, Z., Nie, X.-W., & Bian, J. (2020) · Current Neuropharmacology · doi:10.2174/1570159x18666200905143550 · Cited by 62 · see citing works
Probing the reactivity of singlet oxygen with purines
Dumont, E. E., Grüber, R., Bignon, E., Morell, C., Moreau, Y., Monari, A., & Ravanat, J. (2015) · Nucleic Acids Research · doi:10.1093/nar/gkv1364 · Cited by 60 · see citing works
Self-citationControlled Patterning of Carbon Nanotube Energy Levels by Covalent DNA Functionalization
Zheng, Y., Bachilo, S. M., & Weisman, R. B. (2019) · ACS Nano · doi:10.1021/acsnano.9b03488 · Cited by 57 · see citing works
Sunlight ultraviolet irradiation andBRAFV600 mutagenesis in human melanoma
Nia, A. B., & Pfeifer, G. P. (2008) · Human Mutation · doi:10.1002/humu.20802 · Cited by 57 · see citing works
Stoffels, C., Oumari, M., Perrou, A., Termath, A. O., Schlundt, W., Schmalz, H., Schäfer, M., Wewer, V., Metzger, S. U., Schömig, E., et al. (2017) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2017.10.372 · Cited by 54 · see citing works
Wang, Y., Schanze, K. S., Chi, E. Y., & Whitten, D. G. (2013) · Langmuir · doi:10.1021/la4012263 · Cited by 53 · see citing works
Release of Singlet Oxygen from Organic Peroxides under Mild Conditions
Fudickar, W., & Linker, T. (2018) · ChemPhotoChem · doi:10.1002/cptc.201700235 · Cited by 53 · see citing works
Hirakawa, K., Nishimura, Y., Arai, T., & Okazaki, S. (2013) · The Journal of Physical Chemistry B · doi:10.1021/jp4072444 · Cited by 48 · see citing works
Serrano, M. P., Lorente, C., Borsarelli, C. D., & Thomas, A. H. (2015) · ChemPhysChem · doi:10.1002/cphc.201500219 · Cited by 46 · see citing works
Soares, H. T., Campos, J. R. S., Gomes-da-Silva, L. C., Scháberle, F. A., Dabrowski, J. M., & Arnaut, L. G. (2016) · ChemBioChem · doi:10.1002/cbic.201500573 · Cited by 46 · see citing works
Brooks, P. J. (2016) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2016.12.028 · Cited by 46 · see citing works
Giannakis, S., Gupta, A., Pulgarin, C. O., & Imlay, J. A. (2022) · Water Research · doi:10.1016/j.watres.2022.118740 · Cited by 43 · see citing works
Interaction of Palmatine with DNA: An Environmentally Controlled Phototherapy Drug
Dumont, E. E., & Monari, A. (2014) · The Journal of Physical Chemistry B · doi:10.1021/jp5088515 · Cited by 44 · see citing works
Thymine hydroperoxide as a potential source of singlet molecular oxygen in DNA
Prado, F. M., de Oliveira, M. C. B., Miyamoto, S., Martinez, G. R., de Medeiros, M. H. G., Ronsein, G. E., & Mascio, P. D. (2009) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2009.05.001 · Cited by 41 · see citing works
Self-citationSinglet Oxygen’s Response to Protein Dynamics
Jensen, R. L., Arnbjerg, J., Birkedal, H., & Ogilby, P. R. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2010708 · Cited by 40 · see citing works
Singlet Oxygen Attack on Guanine: Reactivity and Structural Signature within the B‐DNA Helix
Dumont, E. E., Grüber, R., Bignon, E., Morell, C., Aranda, J., Ravanat, J., & Tuñón, I. (2016) · Chemistry - A European Journal · doi:10.1002/chem.201601287 · Cited by 40 · see citing works
Self-citationControl of singlet oxygen production in experiments performed on single mammalian cells
Westberg, M., Bregnhøj, M., Blázquez‐Castro, A., Breitenbach, T., Etzerodt, M., & Ogilby, P. R. (2016) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/j.jphotochem.2016.01.028 · Cited by 39 · see citing works
Technical Considerations for Use of Oligonucleotide Solution API
Müslehiddinoğlu, J., Simler, R., Hill, M. L., Mueller, C., Amery, J., Dixon, L., Watson, A., Storch, K., Gazziola, C., Gielen, F., et al. (2020) · Nucleic Acid Therapeutics · doi:10.1089/nat.2020.0846 · Cited by 38 · see citing works
Zupán, K., Egyeki, M., Tóth, K., Fekete, A., Herényi, L., Módos, K., & Csı́k, G. (2007) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2007.11.007 · Cited by 35 · see citing works
Zahar, N. M. E., Magdy, N., El-Kosasy, A. M., & Bartlett, M. G. (2018) · Analytical and Bioanalytical Chemistry · doi:10.1007/s00216-018-1032-8 · Cited by 33 · see citing works
Caminos, D. A., & Durantini, E. N. (2008) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/j.jphotochem.2008.04.005 · Cited by 33 · see citing works
Leung, E. K. Y., & Sen, D. (2007) · Chemistry & Biology · doi:10.1016/j.chembiol.2006.11.006 · Cited by 33 · see citing works
Zheng, Y., Weight, B. M., Jones, A. C., Chandrasekaran, V., Gifford, B. J., Tretiak, S., Doorn, S. K., & Htoon, H. (2021) · ACS Nano · doi:10.1021/acsnano.0c07544 · Cited by 31 · see citing works
A model to understand type I oxidations of biomolecules photosensitized by pterins
Lorente, C., Serrano, M. P., Vignoni, M., Dántola, M. L., & Thomas, A. H. (2021) · Journal of Photochemistry and Photobiology · doi:10.1016/j.jpap.2021.100045 · Cited by 32 · see citing works
Biflavonoids from Araucaria angustifolia protect against DNA UV-induced damage
Yamaguchi, L. F., Kato, M. J., & Mascio, P. D. (2009) · Phytochemistry · doi:10.1016/j.phytochem.2009.03.003 · Cited by 31 · see citing works
Self-citationCapturing Transient Endoperoxide in the Singlet Oxygen Oxidation of Guanine
Lu, W., & Liu, J. (2016) · Chemistry - A European Journal · doi:10.1002/chem.201504140 · Cited by 31 · see citing works
Zhou, X. M., Wang, Y., Si, J., Zhou, R., Gan, L., Di, C., Xie, Y., & Zhang, H. (2015) · Scientific Reports · doi:10.1038/srep16925 · Cited by 30 · 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-citationExerting better control and specificity with singlet oxygen experiments in live mammalian cells
Westberg, M., Bregnhøj, M., Banerjee, C., Blázquez‐Castro, A., Breitenbach, T., & Ogilby, P. R. (2016) · Methods · doi:10.1016/j.ymeth.2016.07.001 · Cited by 27 · see citing works
Pedersen, B. W., Sinks, L. E., Breitenbach, T., Schack, N. B., Vinogradov, S. A., & Ogilby, P. R. (2011) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2011.00951.x · Cited by 27 · see citing works
Serrano, M. P., Vignoni, M., Lorente, C., Vicendo, P., Oliveros, E., & Thomas, A. H. (2016) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2016.04.196 · Cited by 26 · see citing works
Light Harvesting and Photoemission by Nanoparticles for Photodynamic Therapy
Arguinzoniz, A. G., Ruggiero, E., Habtemariam, A., Hernández‐Gil, J., Salassa, L., & Rivas, J. C. M. (2013) · Particle & Particle Systems Characterization · doi:10.1002/ppsc.201300314 · Cited by 26 · see citing works
Tang, C., Hu, P., Ma, E., Huang, M., & Zheng, Q. (2015) · Dyes and Pigments · doi:10.1016/j.dyepig.2015.01.019 · Cited by 26 · see citing works
Hirakawa, K. (2008) · Analytical and Bioanalytical Chemistry · doi:10.1007/s00216-008-2522-x · Cited by 26 · see citing works
Recent advancements in selenium nanoconstructs as a potential carrier in cancer therapy
Kudarha, R. R., Colaco, V., Gupta, A., Kulkarni, S., Soman, S., Kulkarni, J., Rana, K., Navti, P. D., Tiwari, R., Osmani, R. A. M., et al. (2024) · Nano-Structures & Nano-Objects · doi:10.1016/j.nanoso.2024.101399 · Cited by 25 · see citing works
Piao, M.-J., Lee, N., Chae, S., & Jin, W. H. (2012) · Biological and Pharmaceutical Bulletin · doi:10.1248/bpb.35.873 · Cited by 27 · see citing works
Oxidation of Guanine in Double-Stranded DNA by [Ru(bpy)2dppz]Cl2 in Cationic Reverse Micelles
Evans, S. E., Grigoryan, A., & Szalai, V. A. (2007) · Inorganic Chemistry · doi:10.1021/ic0700708 · Cited by 26 · see citing works
Effect of Bridging Units on Photophysical and DNA Binding Properties of a Few Cyclophanes
Neelakandan, P. P., Sanju, K. S., & Ramaiah, D. (2009) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2009.00660.x · Cited by 24 · see citing works
Serrano, M. P., Estébanez, S., Vignoni, M., Lorente, C., Vicendo, P., Oliveros, E., & Thomas, A. H. (2017) · New Journal of Chemistry · doi:10.1039/c7nj00739f · Cited by 22 · see citing works
Singlet molecular oxygen: Düsseldorf – São Paulo, the Brazilian connection
Mascio, P. D., Martinez, G. R., Miyamoto, S., Ronsein, G. E., de Medeiros, M. H. G., & Cadet, J. (2016) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2015.11.016 · Cited by 21 · see citing works
Self-citationPhotophysics of Acetophenone Interacting with DNA : Why the Road to Photosensitization is Open
Huix‐Rotllant, M., Dumont, E. E., Ferré, N., & Monari, A. (2014) · Photochemistry and Photobiology · doi:10.1111/php.12395 · Cited by 20 · see citing works
Nakamura, T., Son, A., Umehara, Y., Itô, T., Kurihara, R., Ikemura, Y., & Tanabe, K. (2016) · Bioconjugate Chemistry · doi:10.1021/acs.bioconjchem.6b00061 · Cited by 20 · see citing works
Photo-oxidation of cardiolipin and cytochrome c with bilayer-embedded Pc 4
Kim, J. H., Rodríguez, M. E., Oleinick, N. L., & Anderson, V. E. (2010) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2010.05.014 · Cited by 20 · see citing works
Selenium Nanoparticle Enhanced Photodynamic Therapy against Biofilm forming Streptococcus mutans
Haris, Z., & Khan, A. U. (2017) · SSR Institute of International Journal of Life Sciences · doi:10.21276/ijlssr.2017.3.5.4 · Cited by 19 · see citing works
Solar Disinfection as a Water Treatment Technology
Marugán, J., Giannakis, S., McGuigan, K. G., & Polo-López, I. (2020) · Encyclopedia of the UN sustainable development goals · doi:10.1007/978-3-319-70061-8_125-1 · Cited by 19 · see citing works
Pellosi, M. C., Suzukawa, A. A., Scalfo, A. C., Mascio, P. D., Pereira, C. P. M., de Souza-Pinto, N. C., Martins, D. D. L., & Martinez, G. R. (2014) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2014.05.024 · Cited by 18 · see citing works
Self-citationLorente, C., Arzoumanian, E., Castaño, C., Oliveros, E., & Thomas, A. H. (2014) · RSC Advances · doi:10.1039/c3ra46867d · Cited by 18 · see citing works
Lu, W., Teng, H., & Liu, J. (2016) · Physical Chemistry Chemical Physics · doi:10.1039/c6cp01350c · Cited by 18 · see citing works
Kazakov, D. V., & Schmidt, R. (2007) · The Journal of Physical Chemistry A · doi:10.1021/jp070630o · Cited by 17 · see citing works
Tempesti, T. C., STOCKERT, J. C., & Durantini, E. N. (2008) · The Journal of Physical Chemistry B · doi:10.1021/jp808094q · Cited by 17 · see citing works
Is FapyG Mutagenic?: Evidence from the DFT Study
Jena, N. R., & Mishra, P. C. (2013) · ChemPhysChem · doi:10.1002/cphc.201300535 · Cited by 17 · see citing works
Lu, W., Sun, Y., Zhou, W., & Liu, J. (2017) · The Journal of Physical Chemistry B · doi:10.1021/acs.jpcb.7b09515 · Cited by 18 · see citing works
Sun, Y., Tsai, M., Moe, M. M., & Liu, J. (2021) · The Journal of Physical Chemistry A · doi:10.1021/acs.jpca.1c00095 · Cited by 16 · see citing works
Cadet, J., Douki, T., Gasparutto, D., Ravanat, J., & Wagner, J. R. (2009) · Wiley eBooks · doi:10.1002/9780470526279.ch3 · Cited by 16 · see citing works
Self-citationImpact of ecological UV radiation on the photochemistry of nuclear DNA
Sánchez, A. G., Gabrielli, A., & Keszenman, D. J. (2025) · Biophysical Reviews · doi:10.1007/s12551-025-01275-0 · Cited by 16 · see citing works
- Authors
- Cadet, J., Ravanat, J., Martinez, G. R., Medeiros, M. H. G., & Mascio, P. D.
- Affiliations
- Université Joseph Fourier (FR)
- Universidade de São Paulo (BR)
- Corresponding author
- Cadet, Jean
- Venue
- Photochemistry and Photobiology
- Publisher
- Wiley
- Published
- 2006-09
- Volume
- 82
- Issue
- 5
- Pages
- 1219-1225
- ISSN
- 0031-8655 (ISSN-L)
- 1751-1097
- OpenAlex
- W2175848502
- Cited by
- 176
- References
- 76
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 6 · 2023: 9 · 2022: 7 · 2021: 13 · 2020: 5 · 2019: 10 · 2018: 8 · 2017: 11 · 2016: 14 · 2015: 9 · 2014: 11 · 2013: 5 · 2012: 11
- FWCI
- 0.85
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Photochemistry and Photobiology (publishedVersion)
- PubMed (publishedVersion)
- BioOne Complete (BioOne) (submittedVersion)
- 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
- Physical Sciences › Chemistry › Inorganic Chemistry › Metal-Catalyzed Oxygenation Mechanisms
- Keywords
- singlet oxygen, DNA oxidation, guanine, 8-oxo-7,8-dihydroguanine, dioxiranes, quinonoid intermediate, spiroiminodihydantoin, nucleosides, oligonucleotides, cellular DNA, UVA, reaction mechanism, solvent effects
- MeSH terms
- DNA, Guanine, Guanosine, Nucleosides, Oligonucleotides, Oxidation-Reduction, Solvents, Singlet Oxygen
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