Identification of aminobiphenyl derivatives in commercial hair dyes

Chemical Research in Toxicology

Volumn 16, Issue 9, 2003, Pages 1162-1173

  Turesky, Robert J ^a   Freeman, James P ^a   Holland, Ricky D ^a   Nestorick, Daniel M ^a   Miller, Dwight W ^a   Ratnasinghe, D Luke ^a   Kadlubar, Fred F ^a  

^a NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOBIPHENYL; 4 BIPHENYLAMINE; AROMATIC AMINE; HAIR DYE; PHENYLENEDIAMINE; UNCLASSIFIED DRUG;

ARTICLE; BLADDER CANCER; BLADDER CARCINOGENESIS; CHEMICAL CARCINOGENESIS; GAS CHROMATOGRAPHY; HAIR COLOR; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MASS SPECTROMETRY;

AMINOBIPHENYL COMPOUNDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA ADDUCTS; DRUG CONTAMINATION; HAIR DYES; HUMANS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM;

EID: 0141513741     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx030029r     Document Type: Article

References (54)

1. Rehn, L. (1895) Blasengeschwulste bei fuchsinarbeitern. Arch. Klin. Chir. 50, 588-600.
2. Clayson, D. B. (1981) Specific aromatic amines as occupational bladder carcinogens. Natl. Cancer Inst. Monogr., 15-19.
3. Vineis, P., and Pirastu, R. (1997) Aromatic amines and cancer. Cancer Causes Control 8, 346-355.
4. Hazardous substances databank (HSDB) (2003) http://toxnet. nlm.hih.gov.
5. Stavric, B., Klassen, R., and Miles, W. (1979) Gas-liquid chromatographic-mass spectrometric determination of α- and β-naphthylamines in FD&C Red No. 2 (amaranth). J. Assoc. Off. Anal. Chem. 62, 1020-1026.
6. Davis, V. M., and Bailey, J. E., Jr. (1993) Chemical reduction of FD&C yellow No. 5 to determine combined benzidine. J. Chromatogr. 635, 160-164.
7. Garrigos, M. C., Reche, F., Pernias, K., Sanchez, A., and Jimenez, A. (1998) Determination of some aromatic amines in finger-paints for children's use by supercritical fluid extraction combined with gas chromatography. J. Chromatogr. A 819, 259-266.
8. Lancaster, F. E., and Lawrence, J. F. (1999) Determination of benzidine in the food colours tartrazine and sunset yellow FCF, by reduction and derivatization followed by high-performance liquid chromatography. Food Addit. Contam. 16, 381-390.
9. Cioni, F., Bartolucci, G., Pieraccini, G., Meloni, S., and Moneti, G. (1999) Development of a solid-phase microextraction method for detection of the use of banned azo dyes in coloured textiles and leather. Rapid Commun. Mass Spectrom. 13, 1833-1837.
10. Oh, S. W., Kang, M. N., Cho, C. W., and Lee, M. W. (1997) Detection of carcinogenic amines from dyestuffs or dyed substrates. Dyes Pigm. 33, 119-135.
11. Tokiwa, H., Nakagawa, R., and Horikawa, K. (1985) Mutagenic/ carcinogenic agents in indoor pollutants; the dinitropyrenes generated by kerosene heaters and fuel gas and liquefied petroleum gas burners. Mutat. Res. 157, 39-47.
12. Chiang, T. A., Pei-Fen, W., Ying, L. S., Wang, L. F., and Ko, Y. C. (1999) Mutagenicity and aromatic amine content of fumes from heated cooking oils produced in Taiwan. Food Chem. Toxicol. 37, 125-134.
13. Patrianakos, C., and Hoffmann, D. (1979) Chemical studies on tobacco smoke LXIV. On the analysis of aromatic amines in cigarette smoke. J. Assoc. Off. Anal. Chem. 3, 150-154.
14. Department of Health and Human Services, Food and Drug Administration (1985) 21 CFR Parts 74, 81, and 82 (Docket No. 84N-0319) FD&C Yellow No. 5. Fed. Regist. 50, 35774-35783.
15. Reisch, M. S. (2003) Flush with color: Continuing progress in hair dye chemistry satisfies diverse desires of young and old. Chem. Eng. News 81, 25-27.
16. Gago-Dominguez, M., Castelao, J. E., Yuan, J. M., Yu, M. C., and Ross, R. K. (2001) Use of permanent hair dyes and bladder-cancer risk. Int. J. Cancer 91, 575-579.
17. Ames, B. N., Kammen, H. O., and Yamasaki, E. (1975) Hair dyes are mutagenic: identification of a variety of mutagenic ingredients. Proc. Natl. Acad. Sci. U.S.A. 72, 2423-2427.
18. Rojanapo, W., Kupradinun, P., Tepsuwan, A., Chutimataewin, S., and Tanyakaset, M. (1986) Carcinogenicity of an oxidation product of p-phenylenediamine. Carcinogenesis 7, 1997-2002.
19. Hennekens, C. H., Speizer, F. E., Rosner, B., Bain, C. J., Belanger, C., and Peto, R. (1979) Use of permanent hair dyes and cancer among registered nurses. Lancet 1, 1390-1393.
20. Ohno, Y., Aoki, K., Obata, K., and Morrison, A. S. (2003) Case-control study of urinary bladder cancer in metropolitan Nagoya. Natl. Cancer Inst. Monogr. 69, 229-234.
21. Henley, S. J., and Thun, M. J. (2001) Use of permanent hair dyes and bladder-cancer risk. Int. J. Cancer 94, 903-906.
22. Hartge, P., Hoover, R., Altman, R., Austin, D. F., Cantor, K. P., Child, M. A., Key, C, R., Mason, T. J., Marrett, L. D., Myers, M. H., Narayana, A. S., Silverman, D. T., Sullivan, J. W., Swanson, G. M., Thomas, D. B., and West, D. W. (1982) Use of hair dyes and risk of bladder cancer. Cancer Res. 42, 4784-4787.
23. La Vecchia, C., and Tavani, A. (2001) Hair dyes and bladder cancer: an update. Eur. J. Cancer Prev. 10, 205-208.
24. Gago-Dominguez, M., Chan, K. K., Ross, R. K., and Yu, M. C. (2001) Permanent hair dyes and blader cancer risk. Int. J. Cancer 94, 904-906.
25. Yu, M. C., Skipper, P. L., Tannenbaum, S. R., Chan, K. K., and Ross, R. K. (2002) Arylamine exposures and bladder cancer risk. Mutat. Res. 506-507, 21-28.
26. Gago-Dominguez, M., Bell, D. A., Watson, M. A., Yuan, J. M., Castelao, J. E., Hein, D. W., Chan, K. K., Coetzee, G. A., Ross, R. K., and Yu, M. C. (2003) Permanent hair dyes and bladder cancer: risk modification by cytochrome P4501A2 and N-acetyl-transferases 1 and 2. Carcinogenesis 24, 483-489.
27. Golka, K., Prior, V., Blaszkewicz, M., and Bolt, H. M. (2002) The enhanced bladder cancer susceptibility of NAT2 slow acetylators towards aromatic amines: a review considering ethnic differences. Toxicol. Lett. 128, 229-241.
28. Beland, F. A., and Kadlubar, F. (1990) Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. In Chemical Carcinogenesis and Mutagenesis I (Cooper, C. S., Ed.) Vol. 1, pp 267-325, Springer, Berlin.
29. Hein, D. W., Doll, M. A., Fretland, A. J., Gray, K., Deitz, A. C., Feng, Y., Jiang, W., Rustan, T. D., Satran, S. L., and Wilkie, T. R., Sr. (1997) Rodent models of the human acetylation polymorphism: comparisons of recombinant acetyltransferases. Mutat. Res. 376, 101-106.
30. Hein, D. W., Doll, M. A., Fretland, A. J., Leff, M. A., Webb, S. J., Xiao, G. H., Devanaboyina, U. S., Nangju, N. A., and Feng, Y. (2000) Molecular genetics and epidemiology of the NAT1 and NAT2 acetylation polymorphisms. Cancer Epidemiol. Biomarkers Prev. 9, 29-42.
31. Gorlewska-Roberts, K., Green, B., Fares, M., Ambrosone, C. B., and Kadlubar, F. F. (2002) Carcinogen-DNA adducts in human breast epithelial cells. Proc. Am. Assoc. Cancer Res. 43, 1018-1019.
32. Corbett, J. F., and Menkart, J. (1973) Hair Coloring. Cutis 12, 190-197.
33. Brumley, W. C., and Sphon, J. A. (1981) Regulatory mass spectrometry. Biomed. Mass Spectrom. 8, 390-396.
34. Bladwin, R., Bethem, R. A., Boyd, R. K., Budde, W. L., Cairns, T., Gibbons, R. D., Henion, J. D., Kaiser, M. A., Lewis, D. L., Matuski, J. E., Sphon, J. A., Stephany, R. W., and Trubey, R. K. (1997) 1996 ASMS Fall Workshop: Limits to Confirmation, Quantitation, and Detection. J. Am. Soc. Mass Spectrom. 8, 1180-1190.
35. Bryant, M. S., Skipper, P. L., Tannenbaum, S. R., and Maclure, M. (1987) Hemoglobin adducts of 4-aminobiphenyl in smokers and nonsmokers. Cancer Res. 47, 602-608.
36. March, J. (1992) Advanced Organic Chemistry: Reactions, Mechanism and Structure, p 1224, John Wiley & Sons, New York.
37. MacDougall, D., Amore, F. J., Cox, G. V., Crosby, D. G., Estes, F. L., Freeman, D. H., Gibbs, W. E., Gordon, G. E., Keith, L. H., Lal, J., Langner, R. R., McClelland, N. I., Phillips, W. F., Pojasek, R. B., and Sievers, R. E. (1980) Guidelines for data acquistion and data quality evaluation in environmental chemistry. Anal. Chem. 52, 2242-2249.
38. NTP (1982) Carcinogenesis bioassay of 2-biphenylamine hydrochloride in F344/N rats and B6C3F1 mice, NTP Report No. 233.
39. Sphon, J. A. (1978) Use of mass spectrometry for confirmation of animal drug residues. J. Assoc. Off. Anal. Chem. 61, 1247-1252.
40. Platzek, T., Lang, C., Grohmann, G., Gi, U. S., and Baltes, W. (1999) Formation of a carcinogenic aromatic amine from an azo dye by human skin bacteria in vitro. Hum. Exp. Toxicol. 18, 552-559.
41. Chung, K. T., Stevens, S. E., Jr., and Cerniglia, C. E. (1992) The reduction of azo dyes by the intestinal microflora. Crit. Rev. Microbiol. 18, 175-190.
42. Luceri, F., Pieraccini, G., Moneti, G., and Dolara, P. (1993) Primary aromatic amines from side-stream cigarette smoke are common contaminants of indoor air. Toxicol. Ind. Health 9, 405-413.
43. Grimmer, G., Schneider, D., Naujack, K. W., Dettbarn, G., and Jacob, J. (1996) Intercept-reactant method for the determination of aromatic amines in mainstream tobacco smoke. Polycyclic Aromat. Compd. 9, 85-92.
44. PA (P450IA2), the phenacetin O-deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines. Proc. Natl. Acad. Sci. U.S.A. 86, 7696-7700.
45. Skipper, P. L., and Tannenbaum, S. R. (1990) Protein adducts in the molecular dosimetry of chemical carcinogens. Carcinogenesis 11, 507-518.
46. Wolfram, L. J., and Maibach, H. I. (1985) Percutaneous penetration of hair dyes. Arch. Dermatol. Res. 277, 235-241.
47. Yourick, J. J., and Bronaugh, R. L. (2000) Percutaneous penetration and metabolism of 2-nitro-p-phenylenediamine in human and fuzzy rat skin. Toxicol. Appl. Pharmacol. 166, 13-23.
48. Skipper, P. L., Tannenbaum, S. R., Ross, R. K., and Yu, M. C. (2003) Nonsmoking related arylamine exposure and bladder cancer risk. Cancer Epidemiol. Biomarkers Prev. 12, 503-507.
49. German Patent (1907) Actien-Gesellschaft für anilin-fabrikation in Berlin. Verfahren zur Darstellung von p-Phenylendiamin. Patent no. 202170.
50. Zollinger, H. (1961) Diazoamino Compounds. Azo and Diazo Chemistry Aliphatic and Aromatic Compounds, pp 177-189, Interscience Publishers, New York.
51. Sidgwick, N. V. (1966) Aromatic Amines. In The Organic Chemistry of Nitrogen (Millar, I. T., and Springall, H. D., Eds.) pp 140-194, Oxford Press, Oxford.
52. Billing, C. J., and Norman, R. O. C. (1961) The ortho: para-ratio in aromatic substitution. Part IV. The nitration of biphenyl. J. Chem. Soc. 3885-3888.
53. Hegarty, A. A. (1978) Kinetics and mechanisms of reactions involving diazonium and diazo groups. In The Chemistry of Diazonium and Diazo Groups (Patai, S., Ed.) pp 511-592, Wiley, New York.
54. 15N nuclei in the thermal decomposition of diazoaminobenzene (1,3-Diphenyltriazene). Org. Magn. Reson. 5, 429-436.