nitrophenols and 2-amino-5-nitrophenol

Topics: Aniline Compounds; Animals; Carcinogens; Female; Hair Dyes; Humans; Male; Mice; Mice, Inbred Strains; Nitrophenols; Rats; Rats, Inbred F344

An analytical method was developed for the simultaneous determination of 11 aminophenols in direct and oxidized hair dyes by high performance liquid chromatography (HPLC). The samples were extracted with methanol using sodium bisulfite for anti-oxidation. The purification was carried out with the high speed frozen centrifugation. The separation was performed on an Agilent Zorbax SB C18 column with the mobile phases of acetonitrile and an ion pair system of sodium heptanesulfonate and phosphate under a gradient elution. The analytes were detected at three different wavelengths of 230, 270 and 400 nm. In the concentration range of 0.05 - 500 mg/L, the correlation coefficients for the 11 aminophenols were not less than 0.9992. The limits of quantification including 4-amino-3-nitrophenol, 2-amino-5-nitrophenol, and 4-(2-hydroxyethyl) amino-3-nitrophenol were 5 mg/kg. Other aminophenols including 4-aminophenol, 4-methyl aminophenol, 3-aminophenol, 2-aminophenol, 5-amino-o-cresol, 4-amino-3-methylphenol, 5-(2-hydroxyethyl) amino-o-cresol and 2-amino-4-nitrophenol were 20 mg/kg. The recoveries of the aminophenols spiked at different levels ranged from 88.5% to 109. 5% with the relative standard deviations (RSDs) within the range of 2.2% - 8.3%. The commercially available hair dye samples were analyzed for the aminophenols and the results showed that the method was suitable for the determination of the 11 aminophenols in direct and oxidized hair dyes.

Topics: Aminophenols; Aniline Compounds; Chromatography, High Pressure Liquid; Cresols; Hair Dyes; Nitrophenols

Two hair dye components, carcinogenic 4-nitro-2-aminophenol and 5-nitro-2-aminophenol, induced Cu(II)-dependent DNA cleavage frequently at thymine and guanine residues in DNA fragments obtained from the c-Ha-ras-1 protooncogene. When the p53 tumor suppressor gene was used, 4-nitro-2-aminophenol caused Cu(II)-dependent piperidine-labile sites at poly G sequences. In the presence of Cu(II), both components increased 8-oxo-7,8-dihydro-2'-deoxyguanosine formation in DNA. The inhibitory effects of catalase and bathocuproine on DNA damage suggest the involvement of H2O2 and Cu(I). It is speculated that nitro-2-aminophenols undergo Cu(II)-mediated autoxidation to generate active oxygen species causing DNA damage which leads to their carcinogenesis.

Topics: 8-Hydroxy-2'-Deoxyguanosine; Aniline Compounds; Copper; Deoxyguanosine; DNA Damage; Genes, p53; Genes, ras; Hair Dyes; Humans; Nitrophenols; Oxygen