rdf:type |
|
lifeskim:mentions |
umls-concept:C0003075,
umls-concept:C0007026,
umls-concept:C0010843,
umls-concept:C0018321,
umls-concept:C0028953,
umls-concept:C0030011,
umls-concept:C0040087,
umls-concept:C0086972,
umls-concept:C0178499,
umls-concept:C0439807,
umls-concept:C1626935
|
pubmed:issue |
3
|
pubmed:dateCreated |
2008-2-13
|
pubmed:abstractText |
The carbonate radical anion is a biologically important one-electron oxidant that can directly abstract an electron from guanine, the most easily oxidizable DNA base. Oxidation of the 5'-d(CCTACGCTACC) sequence by photochemically generated CO3*- radicals in low steady-state concentrations relevant to biological processes results in the formation of spiroiminodihydantoin diastereomers and a previously unknown lesion. The latter was excised from the oxidized oligonucleotides by enzymatic digestion with nuclease P1 and alkaline phosphatase and identified by LC-MS/MS as an unusual intrastrand cross-link between guanine and thymine. In order to further characterize the structure of this lesion, 5'-d(GpCpT) was exposed to CO3*- radicals, and the cyclic nature of the 5'-d(G*pCpT*) cross-link in which the guanine C8-atom is bound to the thymine N3-atom was confirmed by LC-MS/MS, 1D and 2D NMR studies. The effect of bridging C bases on the cross-link formation was studied in the series of 5'-d(GpC(n)pT) and 5'-d(TpC(n)pG) sequences with n = 0, 1, 2 and 3. Formation of the G*-T* cross-links is most efficient in the case of 5'-d(GpCpT). Cross-link formation (n = 0) was also observed in double-stranded DNA molecules derived from the self-complementary 5'-d(TTACGTACGTAA) sequence following exposure to CO3*- radicals and enzymatic excision of the 5'-d(G*pT*) product.
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pubmed:grant |
|
pubmed:commentsCorrections |
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-10804560,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-11264456,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-11320091,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-11448244,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-11585704,
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http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-12484769,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-12531868,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-12590514,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-12929437,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-14680366,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-14989259,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-15479083,
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http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-16013075,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-16402835,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-16637637,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-16696563,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-16783334,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-16841958,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-17164902,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-17237348,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-2154753,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-2158784,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-26380,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-3241828,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-4414318,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-5036169,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-5845072,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-7578924,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-8619032,
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http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-8924623,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-9134023,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-9149429,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-9358245,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-9588353,
http://linkedlifedata.com/resource/pubmed/commentcorrection/18084033-9760274
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pubmed:language |
eng
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pubmed:journal |
|
pubmed:citationSubset |
IM
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pubmed:chemical |
|
pubmed:status |
MEDLINE
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pubmed:month |
Feb
|
pubmed:issn |
1362-4962
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pubmed:author |
|
pubmed:issnType |
Electronic
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pubmed:volume |
36
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
742-55
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pubmed:dateRevised |
2010-9-22
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pubmed:meshHeading |
pubmed-meshheading:18084033-Anions,
pubmed-meshheading:18084033-Carbonates,
pubmed-meshheading:18084033-Chromatography, Liquid,
pubmed-meshheading:18084033-Cross-Linking Reagents,
pubmed-meshheading:18084033-Cytosine,
pubmed-meshheading:18084033-DNA,
pubmed-meshheading:18084033-DNA Damage,
pubmed-meshheading:18084033-Electrons,
pubmed-meshheading:18084033-Free Radicals,
pubmed-meshheading:18084033-Guanine,
pubmed-meshheading:18084033-Nuclear Magnetic Resonance, Biomolecular,
pubmed-meshheading:18084033-Oligonucleotides,
pubmed-meshheading:18084033-Oxidation-Reduction,
pubmed-meshheading:18084033-Tandem Mass Spectrometry,
pubmed-meshheading:18084033-Thymine
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pubmed:year |
2008
|
pubmed:articleTitle |
Oxidation of single-stranded oligonucleotides by carbonate radical anions: generating intrastrand cross-links between guanine and thymine bases separated by cytosines.
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pubmed:affiliation |
Chemistry Department and Radiation and Solid State Laboratory, 31 Washington Place, New York University, New York, NY 10003-5180, USA.
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pubmed:publicationType |
Journal Article
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