Studies on the miscoding properties of 1,N6-ethenoadenine and 3,N4-ethenocytosine, DNA reaction products of vinyl chloride metabolites, during in vitro DNA synthesis.

No abstract is available for this paper.

• Publication year

  1981

• Venue

  Nucleic Acids Research

• Publication date

  1981-01-24

• Fields of study

  Biology, Medicine, Chemistry

• Identifiers
  DOI 10.1093/NAR/9.2.375PMID 7010314PMCID PMC326699
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Carcinogenicity of chloroethylene oxide, an ultimate reactive metabolite of vinyl chloride, and bis(chloromethyl)ether after subcutaneous administration and in initiation-promotion experiments in mice.

  1980cited by this paper
• Mutagenicity of halogenated aliphatic hydrocarbons in Salmonella typhimurium, Streptomyces coelicolor and Aspergillus nidulans.

  1980cited by this paper
• DNA synthesis with methylated poly(dC-dG) templates. Evidence for a competitive nature to miscoding by O(6)-methylguanine.

  1979cited by this paper
• Effects of depurination on the fidelity of DNA synthesis.

  1979cited by this paper
• Alkylation of RNA by vinyl bromide metabolites in vitro and in vivo

  1979cited by this paper
• Mutagenic and alkylating metabolites of halo-ethylenes, chlorobutadienes and dichlorobutenes produced by rodent or human liver tissues

  1979cited by this paper
• Carcinogenicity of halogenated olefinic and aliphatic hydrocarbons in mice.

  1979cited by this paper
• Mechanism of action of the nitrosoureas -- III. Reactions of bis-chloroethyl nitrosourea and bis-fluoroethyl nitrosourea with adenosine.

  1979cited by this paper
• On the fidelity of DNA replication. Accuracy of Escherichia coli DNA polymerase I.

  1979cited by this paper
• Interactions of vinyl chloride with rat-liver DNA in vivo.

  1978cited by this paper
• Formation of 3,N4-ethenocytidine moieties in RNA by vinyl chloride metabolites in vitro and in vivo

  1978cited by this paper
• New observations concerning the chloroacetaldehyde reaction with some tRNA constituents. Stable intermediates, kinetics and selectivity of the reaction.

  1978cited by this paper
• Interaction of tobacco mosaic virus protein with synthetic polynucleotides containing a fluorescent label: optical properties of poly(A,epsilonA) and poly(C,epsilonC) copolymers and energy migration from the tryptophan to 1,N6-ethenoadenine or 3,N4-ethenocytosine residues in RNP.

  1978cited by this paper
• Preparation and template activities of polynucleotides containing O2- and O4-alkyluridine.

  1978cited by this paper
• Formation and metabolism of alkylated nucleosides: possible role in carcinogenesis by nitroso compounds and alkylating agents.

  1977cited by this paper
• A correlation between the secondary structure of DNA and the reactivity of adenine residues with chloroacetaldehyde.

  1977cited by this paper
• DNA-synthesis with methylated poly(dA-dT) templates: possible role of O4-methylthymine as a pro-mutagenic base.

  1977cited by this paper
• Alkylation of RNA by vinyl chloride metabolites in vitro and in vivo: formation of 1-N(6)-etheno-adenosine.

  1977cited by this paper
• Induction of gene mutations and gene conversions by vinyl chloride metabolites in yeast.

  1977cited by this paper
• Comment on the mutagenic effectiveness of vinyl chloride metabolites.

  1976cited by this paper
• The mutagenicity of chloroethylene oxide, chloroacetaldehyde, 2-chloroethanol and chloroacetic acid, conceivable metabolites of vinyl chloride.

  1976cited by this paper
• Complementary base pairing and the origin of substitution mutations

  1976cited by this paper
• Reaction of 1,3-bis(2-chloroethyl)-1-nitrosourea with synthetic polynucleotides.

  1975cited by this paper
• Liver-microsome-mediated formation of alkylating agents from vinyl bromide and vinyl chloride.

  1975cited by this paper
• Chemical reactivity, metabolic oxirane formation and biological reactivity of chlorinated ethylenes in the isolated perfused rat liver preparation.

  1975cited by this paper
• Mutagenicity of chloroacetaldehyde, a possible metabolic product of 1,2-dichloroethane (ethylene dichloride), chloroethanol (ethylene chlorohydrin), vinyl chloride, and cyclophosphamide.

  1975cited by this paper
• Mutagenic and carcinogenic effects of vinyl chloride.

  1975cited by this paper
• FLUORESCENT NUCLEOSIDES AND NUCLEOTIDES *

  1975cited by this paper
• Mutagenicity of vinyl chloride, chloroethyleneoxide, chloroacetaldehyde and chloroethanol.

  1975cited by this paper
• Mutation induction in chinese hamster V79 cells by two vinyl chloride metabolites, chloroethylene oxide and 2‐chloroacetaldehyde

  1975cited by this paper
• Chloroacetaldehyde-modified dinucleoside phosphates. Dynamic fluorescence quenching and quenching due to intramolecular complexation.

  1974cited by this paper
• Erroneous base-pairing induced by a chemical carcinogen during DNA synthesis

  1974cited by this paper
• Angiosarcoma of liver in the manufacture of polyvinyl chloride.

  1974cited by this paper
• The properties of O 6 -methylguanine in templates for RNA polymerase.

  1973cited by this paper
• Synthesis and properties of a new fluorescent polynucleotide, poly(1,N6-ethenoadenylic acid).

  1973cited by this paper
• Physical studies of chloroacetaldehyde labelled fluorescent DNA.

  1973cited by this paper
• Synthesis and properties of poly (1,N-6-ethenoadenylic acid) and poly (3,N-4-ethenocytidylic acid).

  1973cited by this paper
• Enzymatic activity and - 32 P labeling of fluorescent derivatives of cytidine triphosphate and adenosine triphosphate.

  1973cited by this paper
• A fluorescent analog of nicotinamide adenine dinucleotide.

  1972cited by this paper
• Fluorescent Modification of Adenosine 3',5'-Monophosphate: Spectroscopic Properties and Activity in Enzyme Systems

  1972cited by this paper
• Fluorescent adenosine and cytidine derivatives.

  1972cited by this paper
• Carcinogenicity of halo-ethers. II. Structure-activity relationships of analogs of bis(chloromethyl)ether.

  1972cited by this paper
• Polynucleotides,. XIV. Synthesis and properties of polynucleotides containing 2,6-bis(methylthio)purine ribonucleotides.

  1972cited by this paper
• Polynucleotides. XV. Synthesis and properties of polynucleotides containing N 2 -dimethylguanylic acid residues in polyinosinate and polyadenylate chains.

  1972cited by this paper
• The reaction of guanosine and deoxyguanosine with glycidaldehyde.

  1968cited by this paper

• Upconversion nanohybrids for NIR-induced photorepair of DNA etheno adducts.

  2025cites this paper
• Recognition and Sequencing of Mutagenic DNA Adduct at Single‐Base Resolution Through Unnatural Base Pair

  2024cites this paper
• The Excited State Dynamics of a Mutagenic Guanosine Etheno Adduct Investigated by Femtosecond Fluorescence Spectroscopy and Quantum Mechanical Calculations.

  2024cites this paper
• The Excited State Dynamics of a Mutagenic Cytidine Etheno Adduct Investigated by Combining Time-Resolved Spectroscopy and Quantum Mechanical Calculations

  2021cites this paper
• 1,N6-Ethenoadenine: From Molecular to Biological Consequences†.

  2020cites this paper
• DNA adducts: Formation, biological effects, and new biospecimens for mass spectrometric measurements in humans.

  2018cites this paper
• 1,3-Butadiene-Induced Adenine DNA Adducts Are Genotoxic but Only Weakly Mutagenic When Replicated in Escherichia coli of Various Repair and Replication Backgrounds.

  2017cites this paper
• Differential repair of etheno-DNA adducts by bacterial and human AlkB proteins.

  2015cites this paper
• IDENTIFYING GENETIC DETERMINANTS OF ALKBH2 EVOLVABILITY A thesis submitted in partial satisfaction of the requirements for the degree of MASTER OF SCIENCE in MICROBIOLOGY AND ENVIRONMENTAL TOXICOLOGY By

  2015cites this paper
• Sequence-specific generation of 1,N(6)-ethenoadenine and 3,N(4)-ethenocytosine in single-stranded unmodified DNA.

  2015cites this paper
• I.1. Einleitung

  2015cites this paper
• Model calculations for the base-pairing specificity of mutagenic exocyclic DNA adduct 1,N6-ethenoadenine

  2014cites this paper
• Lipid peroxidation product 4-hydroxy-2-nonenal modulates base excision repair in human cells.

  2014cites this paper
• Nucleic Acid Oxidation in DNA Damage Repair and Epigenetics

  2014cites this paper
• Drinking water disinfection by-products: Toxicological impacts and biological mechanisms induced by individual compounds or as complex mixtures

  2014cites this paper
• An organizational approach for the assessment of DNA adduct data in risk assessment: case studies for aflatoxin B1, tamoxifen and vinyl chloride

  2014cites this paper
• Oxidative stress-induced 1, N6-ethenodeoxyadenosine adduct formation contributes to hepatocarcinogenesis

  2013cites this paper
• Damage of DNA and proteins by major lipid peroxidation products in genome stability

  2012cites this paper
• Oxidatively damaged DNA and its repair in colon carcinogenesis.

  2012cites this paper
• The role of AlkB protein in repair of 1,N⁶-ethenoadenine in Escherichia coli cells.

  2011cites this paper
• Carcinogenic Alkylating Agents

  2010cites this paper
• Oxidative damage to guanine in DNA caused by reactive oxygen species

  2009cites this paper
• Use of oligonucleotides containing ethenoadenine to study the repair of this DNA lesion

  2009cites this paper
• Chapter 6 Pyrimidine Damage and Repair

  2008cites this paper
• Oxidative metabolism of exocyclic DNA adducts.

  2008cites this paper
• Dose-response relationships for mutations induced in E. coli by some model compounds. With an addendum: Reaction kinetics in water of chloroethylene oxide, chloroacetaldehyde, and chloroacetone.

  2008cites this paper
• Inhibition of DNA replication fork progression and mutagenic potential of 1, N6-ethenoadenine and 8-oxoguanine in human cell extracts

  2007cites this paper
• AlkB influences the chloroacetaldehyde-induced mutation spectra and toxicity in the pSP189 supF shuttle vector.

  2007cites this paper
• Increased Etheno-DNA Adducts in Affected Tissues of Patients Suffering from Crohn’s Disease, Ulcerative Colitis, and Chronic Pancreatitis

  2006cites this paper
• Oxidative dealkylation DNA repair mediated by the mononuclear non-heme iron AlkB proteins.

  2006cites this paper
• Apoptosis and age-dependant induction of nuclear and mitochondrial etheno-DNA adducts in Long-Evans Cinnamon (LEC) rats: enhanced DNA damage by dietary curcumin upon copper accumulation.

  2005cites this paper
• Exocyclic DNA lesions stimulate DNA cleavage mediated by human topoisomerase II alpha in vitro and in cultured cells.

  2005cites this paper
• Restricted rotation/tautomeric equilibrium and determination of the site and extent of protonation in bi-imidazole nucleosides by multinuclear NMR and GIAO-DFT calculations

  2005cites this paper
• Age-dependent increase of etheno-DNA-adducts in liver and brain of ROS overproducing OXYS rats.

  2005cites this paper
• Immunohistochemical detection of 1,N6-ethenodeoxyadenosine in nuclei of human liver affected by diseases predisposing to hepato-carcinogenesis.

  2004cites this paper
• Characterization of 2'-deoxycytidine adducts derived from 4-oxo-2-nonenal, a novel lipid peroxidation product.

  2003cites this paper
• Toxic action/toxicity

  2000cites this paper
• Deficiency of N-methylpurine-DNA-glycosylase expression in nonparenchymal cells, the target cell for vinyl chloride and vinyl fluoride.

  2000cites this paper
• Etheno-adduct-forming chemicals: from mutagenicity testing to tumor mutation spectra.

  2000cites this paper
• Mutagenesis induced by a single 1,N6-ethenodeoxyadenosine adduct in human cells.

  2000cites this paper
• Chemistry of Antisense Oligonucleotides

  2000cites this paper
• Role of etheno DNA adducts in carcinogenesis induced by vinyl chloride in rats.

  1999cites this paper
• Detection of 1,N6-etheno-2'-deoxyadenosine and 3,N4-etheno-2'-deoxycytidine occurring endogenously in DNA.

  1999cites this paper
• Keynote address: exocyclic adducts as new risk markers for DNA damage in man.

  1999cites this paper
• Vinyl chloride-specific mutations in humans and animals.

  1999cites this paper
• Solution conformation and mutagenic specificity of 1,N6-ethenoadenine.

  1999cites this paper
• Etheno DNA-base adducts from endogenous reactive species.

  1999cites this paper
• Genetic effects of exocyclic DNA adducts in vivo: heritable genetic damage in comparison with loss of heterozygosity in somatic cells.

  1999cites this paper
• Detection of 1,N6-ethenoadenine in rat urine after chloroethylene oxide exposure.

  1998cites this paper
• Formation of DNA etheno adducts in rodents and humans and their role in carcinogenesis.

  1998cites this paper
• Critical genes as early warning signs: example of vinyl chloride.

  1998cites this paper
• Preferential formation of deletions following in vivo exposure of postmeiotic Drosophila germ cells to the DNA etheno‐adduct‐forming carcinogen vinyl carbamate

  1997cites this paper
• DNA adducts: biological markers of exposure and potential applications to risk assessment.

  1996cites this paper
• 1,N6-ethenodeoxyadenosine, a DNA adduct highly mutagenic in mammalian cells.

  1996cites this paper
• A nine-year follow up study of a population occupationally exposed to vinyl chloride monomer.

  1996cites this paper
• Escherichia coli, Saccharomyces cerevisiae, rat and human 3-methyladenine DNA glycosylases repair 1,N6-ethenoadenine when present in DNA.

  1995cites this paper
• Formation, detection, and role in carcinogenesis of ethenobases in DNA.

  1994cites this paper
• Guanine-1,N6-ethenoadenine base pairs in the crystal structure of d(CGCGAATT(epsilon dA)GCG).

  1994cites this paper
• Mutagenic and genotoxic effects of three vinyl chloride-induced DNA lesions: 1,N6-ethenoadenine, 3,N4-ethenocytosine, and 4-amino-5-(imidazol-2-yl)imidazole.

  1993cites this paper
• Synthesis of 3-(β-D-ribofuranosyl)pyrazolo[3,2-i]-purine derivatives and their cytotoxic activities

  1993cites this paper
• Lösung arbeitsmedizinischer Probleme durch Betriebe und Universitäten — Beispiel Vinylchlorid

  1992cites this paper
• The persistence of sister-chromatid exchange frequencies in men occupationally exposed to vinyl chloride monomer.

  1992cites this paper
• DNA adduct formation by 12 chemicals with populations potentially suitable for molecular epidemiological studies.

  1992cites this paper
• Synthesis of new fluorescent nucleosides, 3-beta-D-ribofuranosylpyrazolo (3,2-i) purine derivatives and their cytotoxic activities.

  1992cites this paper
• Quantitative and kinetic examination of 32P-postlabeling of etheno-substituted nucleotides.

  1991cites this paper
• Activation of Ki‐ras gene by point mutation in human liver angiosarcoma associated with vinyl chloride exposure

  1991cites this paper
• Mechanisms of mutagenesis by exocyclic DNA adducts. Construction and in vitro template characteristics of an oligonucleotide bearing a single site-specific ethenocytosine.

  1991cites this paper
• NMR studies of the exocyclic 1,N6-ethenodeoxyadenosine adduct (epsilon dA) opposite thymidine in a DNA duplex. Nonplanar alignment of epsilon dA(anti) and dT(anti) at the lesion site.

  1991cites this paper
• NMR studies of the exocyclic 1,N6-ethenodeoxyadenosine adduct (epsilon dA) opposite deoxyguanosine in a DNA duplex. Epsilon dA(syn).dG(anti) pairing at the lesion site.

  1991cites this paper
• Methods for the isolation and detection of etheno adducts in nucleotide pools in vivo following exposure to ethyl carbamate.

  1990cites this paper
• Investigations on the relationship between DNA ethenobase adduct levels in several organs of vinyl chloride-exposed rats and cancer susceptibility.

  1990cites this paper
• 2-Chloroacetaldehyde and 2-chloroacetal are potent inhibitors of DNA synthesis in animal cells.

  1990cites this paper
• Mechanisms of mutagenesis by chloroacetaldehyde.

  1989cites this paper
• Roles of etheno-DNA adducts in tumorigenicity of olefins.

  1988cites this paper
• Computational approaches to the identification of suspect toxic molecules.

  1988cites this paper
• Roles of etheno-DNA adducts in tumorigenicity of olefins.

  1988cites this paper
• A computational study of some isomerization equilibria and their possible relation to vinyl chloride carcinogenicity

  1987cites this paper
• Deoxyhexanucleotide containing a vinyl chloride induced DNA lesion, 1,N6-ethenoadenine: synthesis, physical characterization, and incorporation into a duplex bacteriophage M13 genome as part of an amber codon.

  1987cites this paper
• Utilization of 1,N6-etheno-2'-deoxyadenosine 5'-triphosphate during DNA synthesis on natural templates, catalyzed by DNA polymerase I of Escherichia coli.

  1986cites this paper
• Chapter 4 – Mechanisms in perspective: biological significance of modified deoxyribonucleoside residues in DNA

  1986cites this paper
• New adducts of chloroethylene oxide and chloroacetaldehyde with pyrimidine nucleosides.

  1986cites this paper
• Chapter 3 – Authenticated interactions with nucleic acid

  1986cites this paper
• Induction of specific base-pair substitutions in E. coli trpA mutants by chloroethylene oxide, a carcinogenic vinyl chloride metabolite.

  1985cites this paper
• Lack of miscoding properties of 7-(2-oxoethyl)guanine, the major vinyl chloride-DNA adduct.

  1985cites this paper
• Conversion of adenosine to a pentacyclic structure by a 4-nitroquinoline-1-oxide metabolite model.

  1985cites this paper
• High-performance liquid chromatographic purification of deoxynucleoside 5'-triphosphates and their use in a sensitive electrophoretic assay of misincorporation during DNA synthesis.

  1984cites this paper
• Chlorinated ethylenes: their metabolism and effect on DNA repair in rat hepatocytes.

  1984cites this paper
• Etheno-substituted nucleotides and coenzymes: fluorescence and biological activity.

  1984cites this paper
• Molecular Mechanisms of Mutagenesis and Carcinogenesis

  1984cites this paper
• The effect of an epoxide–nucleophile reaction upon hydrogen bonding involving the nucleophile

  1984cites this paper
• Some reactive properties of chlorooxirane, a likely carcinogenic metabolite of vinyl chloride

  1984cites this paper
• Halogenated hydrocarbon epoxides: Factors underlying biological activity

  1984cites this paper
• Reactive properties of trans‐dichlorooxirane in relation to the contrasting carcinogenicities of vinyl chloride and trans‐dichloroethylen

  1984cites this paper
• Assessment of mutagenic efficiency of two carcinogen-modified nucleosides, 1,N6-ethenodeoxyadenosine and O4-methyldeoxythymidine, using polymerases of varying fidelity.

  1984cites this paper
• Errors in DNA synthesis induced by aflatoxin B1 modification of poly(dC-dG).

  1983cites this paper
• In vitro discrimination of replicases acting on carcinogen-modified polynucleotide templates.

  1983cites this paper
• DNA Adducts and Their Biological Relevance

  1983cites this paper
• Persistence of ethyl carbamate-induced DNA damage in vivo as indicated by sister chromatid exchange analysis.

  1983cites this paper
• The formation of acetylaminofluorene adducts in poly(dC-dG) and poly(dA-dT) on reaction with N-acetoxy-2-acetylaminofluorene and the effect of such modification upon the polymers as templates for DNA polymerases.

  1983cites this paper
• Calculated properties of some possible vinyl chloride metabolites

  1982cites this paper