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Identification of new DNA adducts of phenylnitrenium

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F15%3A43899857" target="_blank" >RIV/60461373:22310/15:43899857 - isvavai.cz</a>

  • Result on the web

    <a href="http://dx.doi.org/10.1021/acs.chemrestox.5b00120" target="_blank" >http://dx.doi.org/10.1021/acs.chemrestox.5b00120</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/acs.chemrestox.5b00120" target="_blank" >10.1021/acs.chemrestox.5b00120</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Identification of new DNA adducts of phenylnitrenium

  • Original language description

    Phenylnitrenium ion (PhNH+) may bind to nucleophiles through nitrogen as well as through C2 or C4 carbons. However, only adducts of the former type have been hitherto reported after its reaction with purine nucleosides. In this study, reactions of N-acetoxyaniline (PhNHOAc), a precursor to PhNH+, with 2'-deoxyadenosine (dA), 2'-deoxyguanosine (dG), and with DNA in vitro at physiological conditions are described. The reaction of PhNHOAc with dA followed by a hydrolytic deribosylation afforded 8-phenylaminoadenine (C8-PhNHA) together with a smaller amount of N-6-(4-aminophenyl)adenine (N-6-4APA). A similar reaction with dG afforded 8-phenylaminoguanine (C8-PhNHG) together with traces of 7-(4-aminophenyl)guanine (N7-4APG). The same adducts were found alsoin the DNA treated with PhNHOAc, and all of them were identified by comparison of their HPLC retention times and MSMS spectra with a set of synthesized authentic adenine adducts at C2, C8, N7, and N-6 positions and guanine adducts at C8,

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

  • Continuities

    S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2015

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Chemical Research in Toxicology

  • ISSN

    0893-228X

  • e-ISSN

  • Volume of the periodical

    28

  • Issue of the periodical within the volume

    6

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    9

  • Pages from-to

    1317-1325

  • UT code for WoS article

    000356467300024

  • EID of the result in the Scopus database