Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct in DNA
Language English Country United States Media print
Document type Journal Article
PubMed
7548728
DOI
10.1021/tx00046a002
Knihovny.cz E-resources
- MeSH
- Adenine chemistry metabolism MeSH
- DNA Adducts chemistry metabolism MeSH
- Diazonium Compounds chemistry metabolism MeSH
- Guanine analogs & derivatives chemistry metabolism MeSH
- Microsomes, Liver metabolism MeSH
- Carcinogens chemistry metabolism MeSH
- Rats MeSH
- Naphthols chemistry metabolism MeSH
- Nucleotides metabolism MeSH
- Rats, Sprague-Dawley MeSH
- Cattle MeSH
- Spectrophotometry, Ultraviolet MeSH
- Subcellular Fractions drug effects metabolism MeSH
- In Vitro Techniques MeSH
- Chromatography, High Pressure Liquid MeSH
- Animals MeSH
- Check Tag
- Rats MeSH
- Male MeSH
- Cattle MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- 1-phenylazo-2-naphthol MeSH Browser
- 8-(phenylazo)guanine MeSH Browser
- Adenine MeSH
- DNA Adducts MeSH
- benzenediazonium MeSH Browser
- Diazonium Compounds MeSH
- Guanine MeSH
- Carcinogens MeSH
- Naphthols MeSH
- Nucleotides 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.
References provided by Crossref.org
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