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Identification of Aminobiphenyl Derivatives in Commercial Hair Dyes

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Chem. Res. Toxicol. 2003, 16, 9, 1162-1173
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    Identification of Aminobiphenyl Derivatives in Commercial Hair Dyes
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    Division of Chemistry and Division of Molecular Epidemiology, National Center for Toxicological Research, 3900 NCTR Road, Jefferson, Arkansas 72079
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    Chemical Research in Toxicology

    Cite this: Chem. Res. Toxicol. 2003, 16, 9, 1162–1173
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    https://doi.org/10.1021/tx030029r
    Published August 28, 2003
    Copyright © Not subject to U.S. Copyright. Published 2003 American Chemical Society
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    Abstract

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    A recent epidemiological study suggested that aromatic amines present in hair dyes may contribute to an increased risk of bladder cancer (Gago-Dominguez, et al. (2003) Carcinogenesis24, 483−489). Moreover, a preliminary study linked frequent hair dye usage with elevated levels of DNA adducts of 4-aminobiphenyl (4-ABP) in human epithelial breast cells (Gorlewska, et al. Proc. Am. Assoc. Cancer Res. 43, 1018−1019). Therefore, we sought to determine if 4-ABP, a recognized human urinary bladder carcinogen, is present in commercial hair dyes. 4-ABP was isolated from dyes by solvent extraction with hexane, followed by silica gel chromatography, either with or without chemical treatment of the extract with Zinc/HCl, and a final purification with a mixed cation exchange reversed-phase resin. The identity of 4-ABP was confirmed by both HPLC with electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) and gas chromatography with negative ion chemical ionization mass spectrometry (GC-NICI-MS) following chemical derivatization with pentafluoropropionic anhydride (PFPA). The levels of 4-ABP ranged from not detectable (<0.29 parts per billion (ppb)) up to 12.8 ppb. The noncarcinogenic isomer 2-aminobiphenyl (2-ABP) was also found at quantities up to 310 ppb. 4-ABP was detected in eight of the 11 hair dyes and found in black, red, and blonde hair dyes but not in brown hair dyes. 1,4-Phenylenediamine (PPD) is a key constituent for color development of many permanent hair dyes. Some batches of chemical research grade PPD were contaminated with 4-ABP (up to 500 ppb) and 2-ABP (up to 70 parts per million) and may be a source of ABP contamination in hair dyes. These analytical data demonstrate that 4-ABP is present in some hair dyes. Studies on dermal absorption and bioavailability of 4-ABP from hair dyes are required to determine if this aromatic amine contributes to the increased risk of bladder cancer reported in frequent users of hair dyes.

    Copyright © Not subject to U.S. Copyright. Published 2003 American Chemical Society

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     To whom correspondence should be addressed. Tel:  870-543-7301. Fax:  870-543-7686. E-mail:  [email protected].

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     Division of Chemistry.

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     Division of Molecular Epidemiology.

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    This article is cited by 123 publications.

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    Cite this: Chem. Res. Toxicol. 2003, 16, 9, 1162–1173
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