Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct in DNA
Jazyk angličtina Země Spojené státy americké Médium print
Typ dokumentu časopisecké články
PubMed
7548728
DOI
10.1021/tx00046a002
Knihovny.cz E-zdroje
- MeSH
- adenin chemie metabolismus MeSH
- adukty DNA chemie metabolismus MeSH
- diazoniové sloučeniny chemie metabolismus MeSH
- guanin analogy a deriváty chemie metabolismus MeSH
- jaterní mikrozomy metabolismus MeSH
- karcinogeny chemie metabolismus MeSH
- krysa rodu Rattus MeSH
- naftoly chemie metabolismus MeSH
- nukleotidy metabolismus MeSH
- potkani Sprague-Dawley MeSH
- skot MeSH
- spektrofotometrie ultrafialová MeSH
- subcelulární frakce účinky léků metabolismus MeSH
- techniky in vitro MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- zvířata MeSH
- Check Tag
- krysa rodu Rattus MeSH
- mužské pohlaví MeSH
- skot MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- 1-phenylazo-2-naphthol MeSH Prohlížeč
- 8-(phenylazo)guanine MeSH Prohlížeč
- adenin MeSH
- adukty DNA MeSH
- benzenediazonium MeSH Prohlížeč
- diazoniové sloučeniny MeSH
- guanin MeSH
- karcinogeny MeSH
- naftoly MeSH
- nukleotidy MeSH
1-(Phenylazo)-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) is a liver and urinary bladder carcinogen in mammals. Sudan I forms benzenediazonium ion during cytochrome P-450 catalyzed metabolism. Calf thymus DNA was reacted with Sudan I activated by microsomal enzymes or with benzenediazonium ion in vitro, and the adducts formed were analyzed by the 32P-postlabeling technique. Both enrichment procedures (1-butanol extraction and nuclease P1 digestion) of this technique were employed for detection and quantitation of the DNA adducts formed. Cochromatographic analyses of adduct spots obtained by reaction with DNA or homopolydeoxyribonucleotides showed that the major Sudan I-DNA adduct was formed with deoxyguanosine. This adduct was also found in DNA directly reacted with benzenediazonium ion. The major Sudan I-DNA adduct was characterized by UV/vis absorbance spectroscopy as well as by the chromatographic properties of the adduct on cellulose or poly(ethylenimine)--cellulose TLC and HPLC. The characteristics are identical to those of the adduct synthesized from benzenediazonium ion and guanine, identified by mass, UV/vis, and 1H-NMR spectroscopy as 8-(phenylazo)guanine. The results suggest strongly that benzenediazonium ion derived from Sudan I reacts with DNA in vitro to form the stable 8-(phenylazo)guanine adduct.
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