ArticleNucleic acids research2010
Synthesis and characterization of oligodeoxyribonucleotides containing a site-specifically incorporated N6-carboxymethyl-2'-deoxyadenosine or N4-carboxymethyl-2'-deoxycytidine.
Article in Nucleic acids research, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 18 citations in OpenAlex.
- Formation of Carboxymethyl-Phosphotriester Adducts in DNA.Chemical research in toxicology · 2025Article
- Metabolic Activation and DNA Interactions of CarcinogenicInternational journal of molecular sciences · 2022Review
- DNA replication studies ofThe Journal of biological chemistry · 2019Article
- Replication studies of carboxymethylated DNA lesions in human cells.Nucleic acids research · 2017Article
- Formation of S-[2-(NChemical research in toxicology · 2017Article
- Quantification of Azaserine-Induced Carboxymethylated and Methylated DNA Lesions in Cells by Nanoflow Liquid Chromatography-Nanoelectrospray Ionization Tandem Mass Spectrometry Coupled with the Stable Isotope-Dilution Method.Analytical chemistry · 2016Article
- Roles of Aag, Alkbh2, and Alkbh3 in the Repair of Carboxymethylated and Ethylated Thymidine Lesions.ACS chemical biology · 2016Article
- Simultaneous Quantification of Methylated Cytidine and Adenosine in Cellular and Tissue RNA by Nano-Flow Liquid Chromatography-Tandem Mass Spectrometry Coupled with the Stable Isotope-Dilution Method.Analytical chemistry · 2015Article
- Transcriptional inhibition and mutagenesis induced by N-nitroso compound-derived carboxymethylated thymidine adducts in DNA.Nucleic acids research · 2015Article
- In vitro replication studies of carboxymethylated DNA lesions with Saccharomyces cerevisiae polymerase η.Biochemistry · 2011Article
- High-throughput analysis of the mutagenic and cytotoxic properties of DNA lesions by next-generation sequencing.Nucleic acids research · 2011Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Humans are exposed to both endogenous and exogenous N-nitroso compounds (NOCs), and many NOCs can be metabolically activated to generate a highly reactive species, diazoacetate, which is capable of inducing carboxymethylation of nucleobases in DNA. Here we report, for the first time, the chemical syntheses of authentic N(6)-carboxymethyl-2'-deoxyadenosine (N(6)-CMdA) and N(4)-carboxymethyl-2'-deoxycytidine (N(4)-CMdC), liquid chromatography-ESI tandem MS confirmation of their formation in calf thymus DNA upon diazoacetate exposure, and the preparation of oligodeoxyribonucleotides containing a site-specifically incorporated N(6)-CMdA or N(4)-CMdC. Additionally, thermodynamic studies showed that the substitutions of a dA with N(6)-CMdA and dC with N(4)-CMdC in a 12-mer duplex increased Gibbs free energy for duplex formation at 25°C by 5.3 and 6.8 kcal/mol, respectively. Moreover, primer extension assay revealed that N(4)-CMdC was a stronger blockade to Klenow fragment-mediated primer extension than N(6)-CMdA. The polymerase displayed substantial frequency of misincorporation of dAMP opposite N(6)-CMdA and, to a lesser extent, misinsertion of dAMP and dTMP opposite N(4)-CMdC. The formation and the mutagenic potential of N(6)-CMdA and N(4)-CMdC suggest that these lesions may bear important implications in the etiology of NOC-induced tumor development.
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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 OpenQuestion graph.