| pubmed-article:16351098 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:16351098 | lifeskim:mentions | umls-concept:C0011503 | lld:lifeskim |
| pubmed-article:16351098 | lifeskim:mentions | umls-concept:C0242958 | lld:lifeskim |
| pubmed-article:16351098 | lifeskim:mentions | umls-concept:C1519249 | lld:lifeskim |
| pubmed-article:16351098 | lifeskim:mentions | umls-concept:C1880022 | lld:lifeskim |
| pubmed-article:16351098 | lifeskim:mentions | umls-concept:C0205431 | lld:lifeskim |
| pubmed-article:16351098 | lifeskim:mentions | umls-concept:C0682959 | lld:lifeskim |
| pubmed-article:16351098 | pubmed:issue | 50 | lld:pubmed |
| pubmed-article:16351098 | pubmed:dateCreated | 2005-12-14 | lld:pubmed |
| pubmed-article:16351098 | pubmed:abstractText | The interstrand N2,N2-dG DNA cross-linking chemistry of the acrolein-derived gamma-OH-1,N2-propanodeoxyguanosine (gamma-OH-PdG) adduct in the 5'-CpG-3' sequence was monitored within a dodecamer duplex by NMR spectroscopy, in situ, using a series of site-specific 13C- and 15N-edited experiments. At equilibrium 40% of the DNA was cross-linked, with the carbinolamine form of the cross-link predominating. The cross-link existed in equilibrium with the non-crosslinked N2-(3-oxo-propyl)-dG aldehyde and its geminal diol hydrate. The ratio of aldehyde/diol increased at higher temperatures. The 1,N2-dG cyclic adduct was not detected. Molecular modeling suggested that the carbinolamine linkage should be capable of maintaining Watson-Crick hydrogen bonding at both of the tandem C x G base pairs. In contrast, dehydration of the carbinolamine cross-link to an imine (Schiff base) cross-link, or cyclization of the latter to form a pyrimidopurinone cross-link, was predicted to require disruption of Watson-Crick hydrogen bonding at one or both of the tandem cross-linked C x G base pairs. When the gamma-OH-PdG adduct contained within the 5'-CpG-3' sequence was instead annealed into duplex DNA opposite T, a mixture of the 1,N2-dG cyclic adduct, the aldehyde, and the diol, but no cross-link, was observed. With this mismatched duplex, reaction with the tetrapeptide KWKK formed DNA-peptide cross-links efficiently. When annealed opposite dA, gamma-OH-PdG remained as the 1,N2-dG cyclic adduct although transient epimerization was detected by trapping with the peptide KWKK. The results provide a rationale for the stability of interstrand cross-links formed by acrolein and perhaps other alpha,beta-unsaturated aldehydes. These sequence-specific carbinolamine cross-links are anticipated to interfere with DNA replication and contribute to acrolein-mediated genotoxicity. | lld:pubmed |
| pubmed-article:16351098 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:commentsCorrections | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:language | eng | lld:pubmed |
| pubmed-article:16351098 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:16351098 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:16351098 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:16351098 | pubmed:month | Dec | lld:pubmed |
| pubmed-article:16351098 | pubmed:issn | 0002-7863 | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:HuartJ AJA | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:LloydR... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:RizzoCarmelo... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:JacobJaisonJ | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:MinkoIrina... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:StoneMichael... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:WangHaoH | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:HarrisThomas... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:NechevLubomir... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:KozekovIvan... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:VoehlerMarkus... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:KimHye-YoungH... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:ChoYoung-JinY... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:SlutskyAlvira... | lld:pubmed |
| pubmed-article:16351098 | pubmed:author | pubmed-author:KozekovaAlben... | lld:pubmed |
