Identification of new DNA adducts of phenylnitrenium

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Identification of new DNA adducts of phenylnitrenium

Popis výsledku v původním jazyce

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,

Název v anglickém jazyce

Identification of new DNA adducts of phenylnitrenium

Popis výsledku anglicky

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,

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

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

Rok uplatnění

2015

Kód důvěrnosti údajů

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

Název periodika

Chemical Research in Toxicology

ISSN

0893-228X

e-ISSN

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Svazek periodika

28

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

9

Strana od-do

1317-1325

Kód UT WoS článku

000356467300024

EID výsledku v databázi Scopus

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