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Volumn 130, Issue 26, 2008, Pages 8377-8385

The fate of C5′ radicals of purine nucleosides under oxidative conditions

Author keywords

[No Author keywords available]

Indexed keywords

DNA; FUNCTIONAL GROUPS; GENES; NONMETALS; NUCLEIC ACIDS; NUCLEOTIDES; ORGANIC ACIDS; OXYGEN; RADIATION CHEMISTRY;

EID: 46049091980     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800763j     Document Type: Article
Times cited : (55)

References (73)
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    • (a) Recent results on DNA adducts derived from electrophilic products of 5′-oxidation of deoxyribose in DNA and on oligonucleotides containing 5′-aldehyde at one terminus have been also reported. See: Chen, B.; Vu, C. C.; Byrns, M. C.; Dedon, P. C.; Peterson, L. A. Chem. Res. Toxicol. 2006, 19, 982-985.
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    • These lesions represent a unique class of oxidative DNA lesions in that they are repaired by the nucleotide excision repair pathway but not by base excision repair or direct repair. For a review, see: Brooks, P. J. Neuroscience 2007, 145, 1407-1417
    • These lesions represent a unique class of oxidative DNA lesions in that they are repaired by the nucleotide excision repair pathway but not by base excision repair or direct repair. For a review, see: Brooks, P. J. Neuroscience 2007, 145, 1407-1417.
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    • Ross, A. B.; Mallard, W. G.; Helman, W. P.; Buxton, G. V.; Huie, R. E.; Neta, P. NDRL-NIST Solution Kinetics Database, ver. 3; National Institute of Standards and Technology: Gaithersburg, MD, 1998.
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    • The pH of the solutions decreases from 7.5 to 5.5 when the amount of CySH (0-5 mM) is increased.
    • The pH of the solutions decreases from 7.5 to 5.5 when the amount of CySH (0-5 mM) is increased.
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    • All redox potentials are vs NHE
    • (a) All redox potentials are vs NHE.
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    • -1). See: Candeias, L. P.; Wolf, P.; O'Neill, P.; Steenken, S. J. Phys. Chem. 1992, 96, 10302-10307.
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    • An aqueous solution of 9 or 11 (1 mM) left at room temperature for 24 h and additionally heated at 40°C for 12 h did not result in any decomposition
    • An aqueous solution of 9 or 11 (1 mM) left at room temperature for 24 h and additionally heated at 40°C for 12 h did not result in any decomposition.
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    • Analogous experiments of bromide 6 replacing K3Fe(CN) 6 with FeCl3, CuCl, or CuCl2 were also carried out. In all cases, the yields of 9 were much poorer because of (i) the lower conversion of starting material, the rate constants of eaq, with FeCl3, CuCl, or CuCl2 being 10-20 times faster than that of K3Fe(CN)6,27 and (ii) the formation of similar amounts of 5′,8-cyclo-2′-deoxyadenosine, indicating a slower quenching of C5′ radical by the oxidants FeCl 3, CuCl, or CuCl2
    • 2.
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    • • is 4.8. See: Bielski, B. H. T.; Cabelli, D. E.; Arudi, R. L. J. Phys. Chem. Ref. Data 1985, 14, 1041-1100.
    • • is 4.8. See: Bielski, B. H. T.; Cabelli, D. E.; Arudi, R. L. J. Phys. Chem. Ref. Data 1985, 14, 1041-1100.
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    • 2) = 0.07 produced from the water radiolysis.
    • 2) = 0.07 produced from the water radiolysis.
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    • See Supporting Information for more details
    • (b) See Supporting Information for more details.
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    • We cannot exclude minor paths of radical translocation in the intermediate 7 to positions other than the C5′ of the sugar radical. Theoretical calculation at the B3LYP/6-31G* level suggested that radical translocations to the C5′ and C3′ positions have activation energies of 3.2 and 11.1 kcal mol-1, respectively. See: Chatgilialoglu, C, Duca, M, Ferreri, C, Guerra, M, Ioele, M, Mulazzani, Q. G, Strittmatter, H, Giese, B. Chem, Eur. J. 2004, 10, 1249-1255
    • -1, respectively. See: Chatgilialoglu, C.; Duca, M.; Ferreri, C.; Guerra, M.; Ioele, M.; Mulazzani, Q. G.; Strittmatter, H.; Giese, B. Chem. - Eur. J. 2004, 10, 1249-1255.
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    • The formation of 5′-carboxaldehyde has been reported in the heavy ion-mediated decomposition products of 2′-deoxyguanosine. See: Gromova, M.; Nardin, R.; Cadet, J. J. Chem. Soc., Perkin Trans. 1998, 2, 1365-1374.
    • The formation of 5′-carboxaldehyde has been reported in the heavy ion-mediated decomposition products of 2′-deoxyguanosine. See: Gromova, M.; Nardin, R.; Cadet, J. J. Chem. Soc., Perkin Trans. 1998, 2, 1365-1374.
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    • A similar phenomenon has been also observed in the radiolytic degradation of 2′-deoxyguanosine in aerated aqueous solution. See: Douki, T.; Spinelli, S.; Ravanat, J.-L.; Cadet, J. J. Chem. Soc., Perkin Trans. 1999, 2, 1875-1880.
    • A similar phenomenon has been also observed in the radiolytic degradation of 2′-deoxyguanosine in aerated aqueous solution. See: Douki, T.; Spinelli, S.; Ravanat, J.-L.; Cadet, J. J. Chem. Soc., Perkin Trans. 1999, 2, 1875-1880.
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    • It is possible to estimate roughly the total percentage of HO • radical attacks on the deoxyribose unit by assuming that the free base can result from attacks other than the one to the H5′ position.1,2 The values of G(guanine, 0.03 and Gadenine, 0.06 μmol J-1 were found in the experiments of HO• radical with 23 and 26, respectively. We calculated that ca. 14 and 22% of HO• radicals attack the deoxyribose unit of 2′-deoxyguanosine and 2′-deoxyadenosine, respectively, which is in excellent agreement with the estimated values obtained from the reducing properties of sugar-derived radicals by pulse radiolysis.51,58
    • 51,58


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.