Reactions of benzene oxide, a reactive metabolite of benzene with model nucleophiles and DNA
Identifikátory výsledku
Kód výsledku v 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>
Výsledek na webu
<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>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Reactions of benzene oxide, a reactive metabolite of benzene with model nucleophiles and DNA
Popis výsledku v původním jazyce
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,
Název v anglickém jazyce
Reactions of benzene oxide, a reactive metabolite of benzene with model nucleophiles and DNA
Popis výsledku anglicky
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,
Klasifikace
Druh
J<sub>x</sub> - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)
CEP obor
FP - Ostatní lékařské obory
OECD FORD obor
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Návaznosti výsledku
Projekt
<a href="/cs/project/2B08051" target="_blank" >2B08051: Nová strategie biologického monitorování exposice mutagenům a karcinogenům</a><br>
Návaznosti
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
Ostatní
Rok uplatnění
2012
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Xenobiotica
ISSN
0049-8254
e-ISSN
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Svazek periodika
42
Číslo periodika v rámci svazku
10
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
9
Strana od-do
1028-1037
Kód UT WoS článku
000308411600009
EID výsledku v databázi Scopus
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