Reactions of benzene oxide, a reactive metabolite of benzene with model nucleophiles and DNA
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F12%3A43893495" target="_blank" >RIV/60461373:22310/12:43893495 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.3109/00498254.2012.669872" target="_blank" >http://dx.doi.org/10.3109/00498254.2012.669872</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3109/00498254.2012.669872" target="_blank" >10.3109/00498254.2012.669872</a>
Alternative languages
Result language
angličtina
Original language name
Reactions of benzene oxide, a reactive metabolite of benzene with model nucleophiles and DNA
Original language description
1. Reactivity of benzene oxide (BO), a reactive metabolite of benzene, was studied in model reactions with biologically relevant S- and N-nucleophiles by LC-ESI-MS. 2. Reaction with N-acetylcysteine (NAC) in aqueous buffer solutions gave N-acetyl-S-(6-hydroxycyclohexa-2,4-dien-1-yl)cysteine (pre-mercapturic acid, PPhMA), which was easily dehydrated in acidic solutions to phenylmercapturic acid (PhMA). The yield of PPhMA + PhMA increased exponentially with pH up to 11 % in the pH range from 5.5 to 11.4.3. Primary 6-hydroxycyclohexy-2,4-dien-1-yl (HC) adducts were detected also in reactions purine nucleosides and nucleotides under physiological conditions. After a vigorous acidic hydrolysis, all HC adducts were converted to corresponding phenyl purines,which were identified as 7-phenylguanine (7-PhG), 3-phenyladenine (3-PhA) and N6-phenyladenine (6-PhA). The yield of 7-PhG amounted to 14 ? 5 ppm and 16 ? 7 ppm for 2'-deoxyguanosine and 2'-deoxyguanosine-5'-monophosphate, respectively,
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
FP - Other medical fields
OECD FORD branch
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Result continuities
Project
<a href="/en/project/2B08051" target="_blank" >2B08051: New Strategy for Biological Monitoring of Exposure to Mutagens and Carcinogens</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)<br>S - Specificky vyzkum na vysokych skolach
Others
Publication year
2012
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Xenobiotica
ISSN
0049-8254
e-ISSN
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Volume of the periodical
42
Issue of the periodical within the volume
10
Country of publishing house
GB - UNITED KINGDOM
Number of pages
9
Pages from-to
1028-1037
UT code for WoS article
000308411600009
EID of the result in the Scopus database
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