ArticleNucleic acids research2011
Novel post-synthetic generation, isomeric resolution, and characterization of Fapy-dG within oligodeoxynucleotides: differential anomeric impacts on DNA duplex properties.
Article in Nucleic acids research, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
19 citing papers in PubMed, 28 citations in OpenAlex.
- 8-OxodGuo and Fapy•dG Mutagenicity inChemical research in toxicology · 2024Article
- Discovery adductomics provides a comprehensive portrait of tissue-, age- and sex-specific DNA modifications in rodents and humans.Nucleic acids research · 2023Article
- Forces Driving a Magic Bullet to Its Target: Revisiting the Role of Thermodynamics in Drug Design, Development, and Optimization.Life (Basel, Switzerland) · 2022Review
- Characterization of Aurintricarboxylic Acid (ATA) Interactions with Plasma Transporter Protein and SARS-CoV-2 Viral Targets: Correlation of Functional Activity and Binding Energetics.Life (Basel, Switzerland) · 2022Article
- Structural Dynamics of a Common Mutagenic Oxidative DNA Lesion in Duplex DNA and during DNA Replication.Journal of the American Chemical Society · 2022Article
- Molecular beacons with oxidized bases report on substrate specificity of DNA oxoguanine glycosylases.Chemical science · 2022Article
- Sequence context effects of replication of Fapy•dG in three mutational hot spot sequences of the p53 gene in human cells.DNA repair · 2021Article
- Synthesis of Oligonucleotides Containing the NChemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- A guardian residue hinders insertion of a Fapy•dGTP analog by modulating the open-closed DNA polymerase transition.Nucleic acids research · 2019Article
- Configurational and Conformational Equilibria of NChemical research in toxicology · 2018Article
- Impact of bistrand abasic sites and proximate orientation on DNA global structure and duplex energetics.Biopolymers · 2018Article
- Error-prone replication bypass of the imidazole ring-opened formamidopyrimidine deoxyguanosine adduct.Environmental and molecular mutagenesis · 2017Article
- Synthesis and characterization of oligonucleotides containing a nitrogen mustard formamidopyrimidine monoadduct of deoxyguanosine.Chemical research in toxicology · 2014Article
- Mutagenic spectra arising from replication bypass of the 2,6-diamino-4-hydroxy-N(5)-methyl formamidopyrimidine adduct in primate cells.Chemical research in toxicology · 2013Article
- Unexpected non-Hoogsteen-based mutagenicity mechanism of FaPy-DNA lesions.Nature chemical biology · 2013Article
- Solution structure of duplex DNA containing a β-carba-Fapy-dG lesion.Chemical research in toxicology · 2012Article
- The formamidopyrimidines: purine lesions formed in competition with 8-oxopurines from oxidative stress.Accounts of chemical research · 2012Review
- Regulation of DNA glycosylases and their role in limiting disease.Free radical research · 2012Review
- Chemical and biological consequences of oxidatively damaged guanine in DNA.Free radical research · 2012Review
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Accumulation of damaged guanine nucleobases within genomic DNA, including the imidazole ring opened N(6)-(2-Deoxy-α,β-D-erythro-pentafuranosyl)-2,6-diamino-4-hydroxy-5-formylamidopyrimidine (Fapy-dG), is associated with progression of age-related diseases and cancer. To evaluate the impact of this mutagenic lesion on DNA structure and energetics, we have developed a novel synthetic strategy to incorporate cognate Fapy-dG site-specifically within any oligodeoxynucleotide sequence. The scheme involves the synthesis of an oligonucleotide precursor containing a 5-nitropyrimidine moiety at the desired lesion site via standard solid-phase procedures. Following deprotection and isolation, the Fapy-dG lesion is generated by catalytic hydrogenation and subsequent formylation. NMR assignment of the Fapy-dG lesion (X) embedded within a TXT trimer reveals the presence of rotameric and anomeric species. The latter have been characterized by synthesizing the tridecamer oligodeoxynucleotide d(GCGTACXCATGCG) harboring Fapy-dG as the central residue and developing a protocol to resolve the isomeric components. Hybridization of the chromatographically isolated fractions with their complementary d(CGCATGCGTACGC) counterpart yields two Fapy-dG·C duplexes that are differentially destabilized relative to the canonical G·C parent. The resultant duplexes exhibit distinct thermal and thermodynamic profiles that are characteristic of α- and β-anomers, the former more destabilizing than the latter. These anomer-specific impacts are discussed in terms of differential repair enzyme recognition, processing and translesion synthesis.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the Socratic graph.