- -

Photosensitization of DNA by 5-methyl-2pyrimidone deoxyribonucleoside: (6-4) photoproduct as a posible trojan horse

RiuNet: Institutional repository of the Polithecnic University of Valencia

Share/Send to

Cited by

Statistics

  • Estadisticas de Uso

Photosensitization of DNA by 5-methyl-2pyrimidone deoxyribonucleoside: (6-4) photoproduct as a posible trojan horse

Show full item record

Vendrell Criado, V.; Rodríguez Muñiz, GM.; Cuquerella Alabort, MC.; Lhiaubet, VL.; Miranda Alonso, MÁ. (2013). Photosensitization of DNA by 5-methyl-2pyrimidone deoxyribonucleoside: (6-4) photoproduct as a posible trojan horse. Angewandte Chemie International Edition. 52(25):6476-6479. doi:10.1002/anie.201302176

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/47184

Files in this item

Item Metadata

Title: Photosensitization of DNA by 5-methyl-2pyrimidone deoxyribonucleoside: (6-4) photoproduct as a posible trojan horse
Author: Vendrell Criado, Victoria Rodríguez Muñiz, Gemma María Cuquerella Alabort, Maria Consuelo Lhiaubet, Virginie Lyria Miranda Alonso, Miguel Ángel
UPV Unit: Universitat Politècnica de València. Departamento de Química - Departament de Química
Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química
Issued date:
Abstract:
A (photo)sensitive subject: Combined agarose gel electrophoresis and photochemical studies show that 5-methyl-2-pyrimidone (see picture), the main chromophore of (6-4) photoproducts, behaves as a DNA photosensitizer. These ...[+]
Subjects: Cyclobutane pyrimidine dimers , DNA damage , Photochemistry , Pyrimidones , Triplet excited states
Copyrigths: Cerrado
Source:
Angewandte Chemie International Edition. (issn: 1433-7851 )
DOI: 10.1002/anie.201302176
Publisher:
Wiley-VCH Verlag
Publisher version: http://dx.doi.org/10.1002/anie.201302176
Project ID:
info:eu-repo/grantAgreement/MINECO//CTQ2012-32621/ES/FOTOQUIMICA DE LA FORMACION Y REPARACION DE LESIONES BIPIRIMIDINICAS DE TIPO (6-4), DEWAR Y ESPORA/
info:eu-repo/grantAgreement/MICINN//CTQ2009-13699/ES/CTQ2009-13699/
info:eu-repo/grantAgreement/MINECO//RD12%2F0013%2F0009/ES/REACCIONES ADVERSAS A ALERGENOS Y FARMACOS/
info:eu-repo/grantAgreement/MEC//RYC-2007-00476/ES/RYC-2007-00476/
Thanks:
We gratefully acknowledge support from the Spanish Government (CTQ2009-13699, CTQ2012-32621, RiRAAF RETICS RD12/0013/0009, Ramon y Cajal contract RyC2007-00476 to V.L.-V. and JAE-Predoc 2011-00740 to V.V.-C.).
Type: Artículo

References

Pfeifer, G. P., & Besaratinia, A. (2012). UV wavelength-dependent DNA damage and human non-melanoma and melanoma skin cancer. Photochem. Photobiol. Sci., 11(1), 90-97. doi:10.1039/c1pp05144j

Schärer, O. D. (2003). Chemie und Biologie der DNA-Reparatur. Angewandte Chemie, 115(26), 3052-3082. doi:10.1002/ange.200200523

Schärer, O. D. (2003). Chemistry and Biology of DNA Repair. Angewandte Chemie International Edition, 42(26), 2946-2974. doi:10.1002/anie.200200523 [+]
Pfeifer, G. P., & Besaratinia, A. (2012). UV wavelength-dependent DNA damage and human non-melanoma and melanoma skin cancer. Photochem. Photobiol. Sci., 11(1), 90-97. doi:10.1039/c1pp05144j

Schärer, O. D. (2003). Chemie und Biologie der DNA-Reparatur. Angewandte Chemie, 115(26), 3052-3082. doi:10.1002/ange.200200523

Schärer, O. D. (2003). Chemistry and Biology of DNA Repair. Angewandte Chemie International Edition, 42(26), 2946-2974. doi:10.1002/anie.200200523

Johnson, A. T., & Wiest, O. (2007). Structure and Dynamics of Poly(T) Single-Strand DNA:  Implications toward CPD Formation. The Journal of Physical Chemistry B, 111(51), 14398-14404. doi:10.1021/jp076371k

Liu, Z., Guo, X., Tan, C., Li, J., Kao, Y.-T., Wang, L., … Zhong, D. (2012). Electron Tunneling Pathways and Role of Adenine in Repair of Cyclobutane Pyrimidine Dimer by DNA Photolyase. Journal of the American Chemical Society, 134(19), 8104-8114. doi:10.1021/ja2105009

Li, J., Liu, Z., Tan, C., Guo, X., Wang, L., Sancar, A., & Zhong, D. (2010). Dynamics and mechanism of repair of ultraviolet-induced (6–4) photoproduct by photolyase. Nature, 466(7308), 887-890. doi:10.1038/nature09192

Liu, Z., Tan, C., Guo, X., Kao, Y.-T., Li, J., Wang, L., … Zhong, D. (2011). Dynamics and mechanism of cyclobutane pyrimidine dimer repair by DNA photolyase. Proceedings of the National Academy of Sciences, 108(36), 14831-14836. doi:10.1073/pnas.1110927108

Harrison, C. B., O’Nei, L. L., & Wiest, O. (2005). Computational Studies of DNA Photolyase. The Journal of Physical Chemistry A, 109(32), 7001-7012. doi:10.1021/jp051075y

Sage, E., Girard, P.-M., & Francesconi, S. (2012). Unravelling UVA-induced mutagenesis. Photochem. Photobiol. Sci., 11(1), 74-80. doi:10.1039/c1pp05219e

IKEHATA, H., & ONO, T. (2011). The Mechanisms of UV Mutagenesis. Journal of Radiation Research, 52(2), 115-125. doi:10.1269/jrr.10175

Dessinioti, C., Antoniou, C., Katsambas, A., & Stratigos, A. J. (2010). Basal Cell Carcinoma: What’s New Under the Sun. Photochemistry and Photobiology, 86(3), 481-491. doi:10.1111/j.1751-1097.2010.00735.x

Cadet, J., Mouret, S., Ravanat, J.-L., & Douki, T. (2012). Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions†. Photochemistry and Photobiology, 88(5), 1048-1065. doi:10.1111/j.1751-1097.2012.01200.x

Heil, K., Pearson, D., & Carell, T. (2011). Chemical investigation of light induced DNA bipyrimidine damage and repair. Chem. Soc. Rev., 40(8), 4271-4278. doi:10.1039/c000407n

Haiser, K., Fingerhut, B. P., Heil, K., Glas, A., Herzog, T. T., Pilles, B. M., … Carell, T. (2011). Mechanismus der UV-induzierten Bildung von Dewar-Schäden in DNA. Angewandte Chemie, 124(2), 421-424. doi:10.1002/ange.201106231

Haiser, K., Fingerhut, B. P., Heil, K., Glas, A., Herzog, T. T., Pilles, B. M., … Carell, T. (2011). Mechanism of UV-Induced Formation of Dewar Lesions in DNA. Angewandte Chemie International Edition, 51(2), 408-411. doi:10.1002/anie.201106231

Cech, D., & Holý, A. (1977). Preparation of 2-pyrimidinone nucleosides from uracil nucleosides. Collection of Czechoslovak Chemical Communications, 42(7), 2246-2260. doi:10.1135/cccc19772246

Gildea, B., & McLaughlin, L. W. (1989). The synthesis of 2-pyrimidinone nucleosides and their incorporation into oligodeoxynucleotides. Nucleic Acids Research, 17(6), 2261-2281. doi:10.1093/nar/17.6.2261

Wightman, R., & Holý, A. (1973). Nucleic acid components and their analogues. CLIX. Synthesis of some 2-pyrimidone nucleosides. Collection of Czechoslovak Chemical Communications, 38(5), 1381-1397. doi:10.1135/cccc19731381

Cuquerella, M. C., Lhiaubet-Vallet, V., Cadet, J., & Miranda, M. A. (2012). Benzophenone Photosensitized DNA Damage. Accounts of Chemical Research, 45(9), 1558-1570. doi:10.1021/ar300054e

Cuquerella, M. C., Lhiaubet-Vallet, V., Bosca, F., & Miranda, M. A. (2011). Photosensitised pyrimidine dimerisation in DNA. Chemical Science, 2(7), 1219. doi:10.1039/c1sc00088h

Rodríguez-Muñiz, G. M., Marin, M. L., Lhiaubet-Vallet, V., & Miranda, M. A. (2012). Reactivity of Nucleosides with a Hydroxyl Radical in Non-aqueous Medium. Chemistry - A European Journal, 18(26), 8024-8027. doi:10.1002/chem.201201090

Bosca, F., Lhiaubet-Vallet, V., Cuquerella, M. C., Castell, J. V., & Miranda, M. A. (2006). The Triplet Energy of Thymine in DNA. Journal of the American Chemical Society, 128(19), 6318-6319. doi:10.1021/ja060651g

Douki, T., Court, M., & Cadet, J. (2000). Electrospray–mass spectrometry characterization and measurement of far-UV-induced thymine photoproducts. Journal of Photochemistry and Photobiology B: Biology, 54(2-3), 145-154. doi:10.1016/s1011-1344(00)00009-9

LION, Y., DELMELLE, M., & VAN DE VORST, A. (1976). New method of detecting singlet oxygen production. Nature, 263(5576), 442-443. doi:10.1038/263442a0

Motten, A. G., Buettner, G. R., & Chignell, C. F. (1985). SPECTROSCOPIC STUDIES OF CUTANEOUS PHOTOSENSITIZING AGENTS–VIII. A SPIN-TRAPPING STUDY OF LIGHT INDUCED FREE RADICALS FROM CHLORPROMAZINE and PROMAZINE. Photochemistry and Photobiology, 42(1), 9-15. doi:10.1111/j.1751-1097.1985.tb03540.x

Samuni, A., Goldstein, S., Russo, A., Mitchell, J. B., Krishna, M. C., & Neta, P. (2002). Kinetics and Mechanism of Hydroxyl Radical and OH-Adduct Radical Reactions with Nitroxides and with Their Hydroxylamines. Journal of the American Chemical Society, 124(29), 8719-8724. doi:10.1021/ja017587h

Fingerhut, B. P., Herzog, T. T., Ryseck, G., Haiser, K., Graupner, F. F., Heil, K., … Zinth, W. (2012). Dynamics of ultraviolet-induced DNA lesions: Dewar formation guided by pre-tension induced by the backbone. New Journal of Physics, 14(6), 065006. doi:10.1088/1367-2630/14/6/065006

[-]

recommendations

 

This item appears in the following Collection(s)

Show full item record