ArticleJournal of the American Chemical Society2015
N7 methylation alters hydrogen-bonding patterns of guanine in duplex DNA.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 59 papers, 4 of them syntheses that pooled it.
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Who cites it
59 citing papers in PubMed, 4 syntheses or guidelines pooled it.
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- Conditional disease-free survival in high-risk renal cell carcinoma treated with sunitinib.Aging · 2019Trial
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- Synthesis and Characterization of Chemically Stable N7-dG Estrone and Catechol Adducts.Molecules (Basel, Switzerland) · 2026Article
- Multi-site DMS probing reveals higher-order structure of RNA-protein complexes in living cells.Molecular cell · 2026Article
- Can pristine/modified graphene repair N7-methylated guanine lesions? A DFT study.Journal of molecular modeling · 2025Article
- Kinetics and dynamics of oligonucleotide hybridization.Nature reviews. Chemistry · 2025Review
- Structural Insights into the Nonmutagenicity of 2-Haloacetophenone.Molecules (Basel, Switzerland) · 2025Article
- Quantification of Intracellular DNA-Protein Cross-Links with N7-Methyl-2'-Deoxyguanosine and Their Contribution to Cytotoxicity.Chemical research in toxicology · 2024Article
- Trans-lesion synthesis and mismatch repair pathway crosstalk defines chemoresistance and hypermutation mechanisms in glioblastoma.Nature communications · 2024Article
- Trans-Lesion Synthesis and Mismatch Repair Pathway Crosstalk Defines Chemoresistance and Hypermutation Mechanisms in Glioblastoma.bioRxiv : the preprint server for biology · 2023Article
- Polymeric nanoparticles for DNA vaccine-based cancer immunotherapy: a review.Biotechnology letters · 2023Review
- Genotoxic effects of the major alkylation damage N7-methylguanine and methyl formamidopyrimidine.The Biochemical journal · 2023Article
- Local Alteration of Ionic Strength in a Nucleosome Core Particle and Its Effect onBiochemistry · 2022Article
- Structural Dynamics of a Common Mutagenic Oxidative DNA Lesion in Duplex DNA and during DNA Replication.Journal of the American Chemical Society · 2022Article
- Structure-activity features of purines and their receptors: implications in cell physiopathology.Molecular biomedicine · 2022Review
- Effect of N7-methylation on base pairing patterns of guanine: a DFT study.Journal of molecular modeling · 2021Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
N7-Alkyl-2'-deoxyguanosines are major adducts in DNA that are generated by various alkylating mutagens and drugs. However, the effect of the N7 alkylation on the hydrogen-bonding patterns of the guanine remains poorly understood. We prepared N7-methyl-2'-deoxyguanosine (N7mdG)-containing DNA using a transition-state destabilization strategy, developed a novel polβ-host-guest complex system, and determined eight crystal structures of N7mdG or dG paired with dC, dT, dG, and dA. The structures of N7mdG:dC and N7mdG:dG are very similar to those of dG:dC and dG:dG, respectively, indicating the involvement of the keto tautomeric form of N7mdG in the base pairings with dC and dG. On the other hand, the structure of N7mdG:dT shows that the mispair forms three hydrogen bonds and adopts a Watson-Crick-like geometry rather than a wobble geometry, suggesting that the enol tautomeric form of N7mdG involves in its base pairing with dT. In addition, N7mdG:dA adopts a novel shifted anti:syn base pair presumably via the enol tautomeric form of N7mdG. The polβ-host-guest complex structures reveal that guanine-N7 methylation changes the hydrogen-bonding patterns of the guanine when paired with dT or dA and suggest that N7 alkylation may alter the base pairing patterns of guanine by promoting the formation of the rare enol tautomeric form of guanine.
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