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Volumn 8, Issue 7, 1995, Pages 924-933

γ Irradiation of 2'-Deoxyadenosine in Oxygen-Free Aqueous Solutions: Identification and Conformational Features of Formamidopyrimidine Nucleoside Derivatives

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYADENOSINE; NUCLEOSIDE DERIVATIVE; PYRIMIDINE DERIVATIVE;

EID: 0028841039     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00049a005     Document Type: Article
Times cited : (42)

References (36)
  • 1
    • 0027180956 scopus 로고
    • Effects of radiation of different qualities on cells: molecular mechanism of damage and repair
    • Goodhead, D. T., Thacker, J., and Cox, R. (1993) Effects of radiation of different qualities on cells: molecular mechanism of damage and repair. Int. J. Radiat. Biol. 63, 536–543.
    • (1993) Int. J. Radiat. Biol. , vol.63 , pp. 536-543
    • Goodhead, D.T.1    Thacker, J.2    Cox, R.3
  • 2
    • 0024195429 scopus 로고
    • DNA damage produced by ionizing radiation in mammalian cells. Identities, mechanism of formation and repairability
    • Ward, J. F. (1988) DNA damage produced by ionizing radiation in mammalian cells. Identities, mechanism of formation and repairability. Prog. Nucleic Acid Res. Mol. Biol. 35, 95–125.
    • (1988) Prog. Nucleic Acid Res. Mol. Biol. , vol.35 , pp. 95-125
    • Ward, J.F.1
  • 5
    • 0028691021 scopus 로고
    • DNA damage caused by oxidation, deamination, ultraviolet radiation and photoexcited psoralens
    • (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) IARC Scientific Publications 125, International Agency for Research on Cancer, Lyon
    • Cadet, J. (1994) DNA damage caused by oxidation, deamination, ultraviolet radiation and photoexcited psoralens. In DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) IARC Scientific Publications 125, pp 245–276, International Agency for Research on Cancer, Lyon.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 245-276
    • Cadet, J.1
  • 6
    • 0028315896 scopus 로고
    • Thymidine hydroperoxides. Structural assignment, conformational features, and thermal decomposition in water
    • Wagner, J. R., van Lier, J. E., Berger, M., and Cadet, J. (1994) Thymidine hydroperoxides. Structural assignment, conformational features, and thermal decomposition in water. J. Am. Chem. Soc. 116, 2235–2242.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2235-2242
    • Wagner, J.R.1    van Lier, J.E.2    Berger, M.3    Cadet, J.4
  • 8
    • 0017910941 scopus 로고
    • Radiation-induced degradation of the base component in DNA and related substances—Final products
    • Téoule, R. and Cadet, J. (1978) Radiation-induced degradation of the base component in DNA and related substances—Final products. Mol. Biol. Biochem. Biophys. 27, 171–203.
    • (1978) Mol. Biol. Biochem. Biophys , vol.27 , pp. 171-203
    • Téoule, R.1    Cadet, J.2
  • 9
    • 0000163631 scopus 로고
    • The chemical consequences of radiation damage to DNA
    • Becker, P., and Sevilla, M. D. (1993) The chemical consequences of radiation damage to DNA. Adv. Radiat. Biol. 17, 121–180.
    • (1993) Adv. Radiat. Biol. , vol.17 , pp. 121-180
    • Becker, P.1    Sevilla, M.D.2
  • 10
    • 33748366270 scopus 로고
    • - and OH adducts
    • - and OH adducts. Chem. Rev. 89, 503–520.
    • (1989) Chem. Rev. , vol.89 , pp. 503-520
    • Steenken, S.1
  • 11
    • 0021957619 scopus 로고
    • Radiation-induced decomposition of the purine bases within DNA and related compounds
    • Cadet, J., and Berger, M. (1985) Radiation-induced decomposition of the purine bases within DNA and related compounds. Int. J. Radiat. Biol. 47, 127–143.
    • (1985) Int. J. Radiat. Biol. , vol.47 , pp. 127-143
    • Cadet, J.1    Berger, M.2
  • 12
    • 33845281363 scopus 로고
    • Pattern of OH radical reaction with 6- and 9-substituted purines. Effect of substituents on the rates and activation parameters of the unimolecular transformation reactions of two isomeric OH adducts
    • Vieira, A. J. S. C., and Steenken, S. (1987) Pattern of OH radical reaction with 6- and 9-substituted purines. Effect of substituents on the rates and activation parameters of the unimolecular transformation reactions of two isomeric OH adducts. J. Phys. Chem. 91, 4138–4144.
    • (1987) J. Phys. Chem. , vol.91 , pp. 4138-4144
    • Vieira, A.J.S.1    Steenken, S.2
  • 13
    • 0002738322 scopus 로고
    • Formation of 8-hydroxydeoxyguanosine in DNA by oxygen radicals and its biological significance
    • (Sies, H., Ed.) Academic Press, New York
    • Kasai, H., and Nishimura, S. (1991) Formation of 8-hydroxydeoxyguanosine in DNA by oxygen radicals and its biological significance. In Oxidative Stress, Oxidants and Antioxidants (Sies, H., Ed.) pp 99–116, Academic Press, New York.
    • (1991) Oxidative Stress, Oxidants and Antioxidants , pp. 99-116
    • Kasai, H.1    Nishimura, S.2
  • 14
    • 0025127407 scopus 로고
    • Pattern of OH radical reaction with adenine and its nucleosides and nucleotides. Characterization of two types of isomeric OH adduct and their unimolecular transformation reactions
    • Vieira, A. J. S. C., and Steenken, S. (1990) Pattern of OH radical reaction with adenine and its nucleosides and nucleotides. Characterization of two types of isomeric OH adduct and their unimolecular transformation reactions. J. Am. Chem. Soc. 112, 6986–6994.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6986-6994
    • Vieira, A.J.S.1    Steenken, S.2
  • 15
    • 0001434563 scopus 로고
    • Isolation and characterization of the radiation-induced degradation products of 2'-deoxyguanosine in oxygen-free aqueous solutions
    • Berger, M., and Cadet, J. (1985) Isolation and characterization of the radiation-induced degradation products of 2'-deoxyguanosine in oxygen-free aqueous solutions. Z. Naturforsch. 40b, 1519–1531.
    • (1985) Z. Naturforsch. , vol.40b , pp. 1519-1531
    • Berger, M.1    Cadet, J.2
  • 16
    • 0015078607 scopus 로고
    • The decomposition of adenine by ionizing radiation
    • van Hemmen, J. J., and Bleichrodt, J. F. (1971) The decomposition of adenine by ionizing radiation. Radiat. Res. 46, 444–456.
    • (1971) Radiat. Res. , vol.46 , pp. 444-456
    • van Hemmen, J.J.1    Bleichrodt, J.F.2
  • 17
    • 0018581985 scopus 로고
    • A new radiolysis mechanism for 2'adenosine in aqueous deaerated solution
    • Mariaggi, N., Téoule, R., Cadet, J., Dickie, H., and Hughes, E. (1979) A new radiolysis mechanism for 2'adenosine in aqueous deaerated solution. Radiat. Res. 79, 431–438.
    • (1979) Radiat. Res. , vol.79 , pp. 431-438
    • Mariaggi, N.1    Téoule, R.2    Cadet, J.3    Dickie, H.4    Hughes, E.5
  • 18
    • 49549131109 scopus 로고
    • Cyclisation radicalaire de la désoxy-2'-adénosine en solution aqueuse, sous l'effet du rayonnement gamma (γ-Radiolytic induced radical cyclization of 2'-deoxyadenosine in aqueous solution)
    • Mariaggi, N., Cadet, J., and Téoule, R. (1976) Cyclisation radicalaire de la désoxy-2'-adénosine en solution aqueuse, sous l'effet du rayonnement gamma (γ-Radiolytic induced radical cyclization of 2'-deoxyadenosine in aqueous solution). Tetrahedron 32, 2385–2387.
    • (1976) Tetrahedron , vol.32 , pp. 2385-2387
    • Mariaggi, N.1    Cadet, J.2    Téoule, R.3
  • 20
    • 0019202657 scopus 로고
    • Quantitative reversed-phase high performance liquid chromatography determination of major and modified deoxyribonucleosides in DNA
    • Kuo, K. C., McCune, R. A., and Gehrke, C. W. (1980) Quantitative reversed-phase high performance liquid chromatography determination of major and modified deoxyribonucleosides in DNA. Nucleic Acids Res. 8, 4763–4776.
    • (1980) Nucleic Acids Res. , vol.8 , pp. 4763-4776
    • Kuo, K.C.1    McCune, R.A.2    Gehrke, C.W.3
  • 21
    • 84989132991 scopus 로고
    • 13C NMR spectra of 8-oxoguanosine and 8-oxoadenosine
    • 13C NMR spectra of 8-oxoguanosine and 8-oxoadenosine. Magn. Reson. Chem. 31, 1048–1053.
    • (1993) Magn. Reson. Chem. , vol.31 , pp. 1048-1053
    • Cho, B.P.1
  • 22
    • 0000762913 scopus 로고
    • 1H chemical shifts in natural-abundance samples via multiple quantum coherence
    • 1H chemical shifts in natural-abundance samples via multiple quantum coherence. J. Am. Chem. Soc. 105, 7188–7190.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 7188-7190
    • Bax, A.1    Giffey, R.H.2    Hawkins, B.L.3
  • 24
    • 0001749729 scopus 로고
    • Studies of tautomers and protonation of adenine and its derivatives by nitrogen-15 nuclear magnetic resonance spectroscopy
    • Gonnella, N. C., Nakanishi, H., Holtwick, J. B., Horowitz, D. S., Kanamori, K., Leonard, N. J., and Roberts, J. D. (1983) Studies of tautomers and protonation of adenine and its derivatives by nitrogen-15 nuclear magnetic resonance spectroscopy. J. Am. Chem. Soc. 105, 2050–2055.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2050-2055
    • Gonnella, N.C.1    Nakanishi, H.2    Holtwick, J.B.3    Horowitz, D.S.4    Kanamori, K.5    Leonard, N.J.6    Roberts, J.D.7
  • 25
    • 0019335254 scopus 로고
    • Conformational studies of α- and β-pyrimidine 2'-deoxyribonucleosides in the syn and anti conformation
    • Cadet, J., Taïeb, C., Remin, M., Niemczura, W. P., and Hruska, F. E. (1980) Conformational studies of α- and β-pyrimidine 2'-deoxyribonucleosides in the syn and anti conformation. Biochim. Biophys. Acta 608, 435–445.
    • (1980) Biochim. Biophys. Acta , vol.608 , pp. 435-445
    • Cadet, J.1    Taïeb, C.2    Remin, M.3    Niemczura, W.P.4    Hruska, F.E.5
  • 26
    • 0023199083 scopus 로고
    • Reaction of acid-activated mitomycin C with calf thymus DNA and model guanines: elucidation of the base-catalyzed degradation of N7-alkylguanine nucleosides
    • Tomasz, M., Lipman, R., Lee, M. S., Verdine, G. L., and Nakanishi, K. (1987) Reaction of acid-activated mitomycin C with calf thymus DNA and model guanines: elucidation of the base-catalyzed degradation of N7-alkylguanine nucleosides. Biochemistry 26, 2010–2027.
    • (1987) Biochemistry , vol.26 , pp. 2010-2027
    • Tomasz, M.1    Lipman, R.2    Lee, M.S.3    Verdine, G.L.4    Nakanishi, K.5
  • 27
    • 0015913888 scopus 로고
    • Conformational analysis of the sugar ring in nucleosides and nucleotides. Improved method for the interpretation of proton magnetic resonance coupling constants
    • Altona, C., and Sundaralingam, M. (1973) Conformational analysis of the sugar ring in nucleosides and nucleotides. Improved method for the interpretation of proton magnetic resonance coupling constants. J. Am. Chem. Soc. 95, 2333–2344.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 2333-2344
    • Altona, C.1    Sundaralingam, M.2
  • 28
    • 0023763262 scopus 로고
    • Formation of cyclopyrimidines via the direct effects of gamma radiation of pyrimidine nucleosides
    • Shaw, A. A., and Cadet, J. (1988) Formation of cyclopyrimidines via the direct effects of gamma radiation of pyrimidine nucleosides. Int. J. Radiat. Biol. 54, 987–997.
    • (1988) Int. J. Radiat. Biol. , vol.54 , pp. 987-997
    • Shaw, A.A.1    Cadet, J.2
  • 29
    • 0000668404 scopus 로고
    • Characterization of thymidine ultraviolet photoproducts. Cyclobutane dimers and 5,6-dihydrothymidines
    • Cadet, J., Voituriez, L., Hruska, F. E., Kan, L.-S., de Leeuw, F. A. A. M., and Altona, C. (1985) Characterization of thymidine ultraviolet photoproducts. Cyclobutane dimers and 5,6-dihydrothymidines. Can. J. Chem. 63, 2861–2868.
    • (1985) Can. J. Chem. , vol.63 , pp. 2861-2868
    • Cadet, J.1    Voituriez, L.2    Hruska, F.E.3    Kan, L.-S.4    de Leeuw, F.A.A.M.5    Altona, C.6
  • 30
    • 0021760535 scopus 로고
    • Two rotameric forms of open ring 7-methylguanine are present in alkylated polynucleotides
    • Boiteux, S., Belleney, J., Roques, B. P., and Laval, J. (1984) Two rotameric forms of open ring 7-methylguanine are present in alkylated polynucleotides. Nucleic Acids Res. 12, 5429–5439.
    • (1984) Nucleic Acids Res. , vol.12 , pp. 5429-5439
    • Boiteux, S.1    Belleney, J.2    Roques, B.P.3    Laval, J.4
  • 31
    • 84981904438 scopus 로고
    • Detection of hindered rotation and inversion by NMR spectroscopy
    • Kessler, H. (1970) Detection of hindered rotation and inversion by NMR spectroscopy. Angew. Chem., Int. Ed. Engl. 9, 219–235.
    • (1970) Angew. Chem., Int. Ed. Engl. , vol.9 , pp. 219-235
    • Kessler, H.1
  • 32
    • 0003321684 scopus 로고
    • Applications of dynamic NMR spectroscopy to organic chemistry
    • VCH Publishers, Deerfield Beach, FL
    • Oki, M. (1985) Applications of dynamic NMR spectroscopy to organic chemistry. Methods Stereochem. Anal. 4, VCH Publishers, Deerfield Beach, FL.
    • (1985) Methods Stereochem. Anal. , vol.4
    • Oki, M.1
  • 33
    • 0000463227 scopus 로고
    • 13C NMR study of the radiation-induced degradation products of 2'-deoxythymidine derivatives: N-(2-deoxy-β-D-erythro-pentofuranosyl)formamide
    • 13C NMR study of the radiation-induced degradation products of 2'-deoxythymidine derivatives: N-(2-deoxy-β-D-erythro-pentofuranosyl)formamide. Can. J. Chem. 59, 3313–3318.
    • (1981) Can. J. Chem. , vol.59 , pp. 3313-3318
    • Cadet, J.1    Nardin, R.2    Voituriez, L.3    Remin, M.4    Hruska, F.E.5
  • 35
    • 0026533905 scopus 로고
    • Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): excision of purine lesions in DNA produced by ionizing radiation or photosensitization
    • Boiteux, S., Gajewski, E., Laval, J., and Dizdaroglu, M. (1992) Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): excision of purine lesions in DNA produced by ionizing radiation or photosensitization. Biochemistry 31, 106–110.
    • (1992) Biochemistry , vol.31 , pp. 106-110
    • Boiteux, S.1    Gajewski, E.2    Laval, J.3    Dizdaroglu, M.4


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