A new way to carcinogenicity of azo dyes: the benzenediazonium ion formed from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene(Sudan I) by microsomal enzymes binds to deoxyguanosine residues of DNA.
1-Phenylazo-2-hydroxynaphthalene (Sudan I) activated by pre-incubation with microsomal enzymes of rat livers covalently binds to DNA from calf thymus. Benzenediazonium ion formed from Sudan I by activation with microsomal enzymes is the principal active metabolite, which binds to DNA. Enzymatic hydrolysis of modified (14C-labelled) DNA, followed by separation of deoxynucleosides on a Sephadex G-10 column revealed that deoxyguanosine is the principal target for the binding of activated Sudan I. The high-performance liquid chromatographic (HPLC) analysis indicate that probably more than one radioactive adduct of activated Sudan I with deoxyguanosine is formed.
Stiborová
M
M
Department of Biochemistry, Faculty of Natural Sciences, Charles University, Prague, Czechoslovakia.
Asfaw
B
B
Anzenbacher
P
P
Hodek
P
P
D000818:Animals; D001711:Biotransformation; D002273:Carcinogens; D002851:Chromatography, High Pressure Liquid; D004396:Coloring Agents; D004247:DNA / Q000378:metabolism; D003849:Deoxyguanosine / Q000378:metabolism*; D003979:Diazonium Compounds / Q000378:metabolism*; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D009284:Naphthols / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains
D002273:Carcinogens; D004396:Coloring Agents; D003979:Diazonium Compounds; D009284:Naphthols; C035176:benzenediazonium; C024336:1-phenylazo-2-naphthol; D004247:DNA; D003849:Deoxyguanosine