4-Aminobiphenyl
4-Aminobiphenyl is a derivative of biphenyl. It is used to manufacture azo dyes. It is a known human carcinogen and so it has been largely replaced by less toxic compounds. It is similar to benzidine.
Because of its carcinogenic effects, 4-aminobiphenyl has not been produced commercially in the United States since the mid 1950s, and is used only for research purposes. Since 4-aminobiphenyl was reviewed for listing in the First Annual Report on Carcinogens, most research on its carcinogenicity has focused on exposure from cigarette smoking. Epidemiological studies have reported the incidence of bladder cancer to be 2 to 10 times as high among cigarette smokers as among nonsmokers. Higher levels of 4-aminobiphenyl adducts (4-aminobiphenyl metabolites bound to DNA or protein) were detected in bladder tumors (DNA adducts) and red blood cells (hemoglobin adducts) from smokers than from nonsmokers (as reviewed by Feng et al. 2002).
In a case-control study, levels of 4-aminobiphenyl hemoglobin adducts were higher in smokers with bladder cancer than in a control group of similarly exposed smokers (Del Santo et al. 1991). A Taiwanese study reported that 4-aminobiphenyl hemoglobin adducts were associated with increased risk of liver cancer (Wang et al. 1998).
There is sufficient evidence for the carcinogenicity of 4- aminobiphenyl in experimental animals as demonstrated by studies showing that 4-aminobiphenyl causes cancer in rats, mice, rabbits, and dogs. When administered orally, 4-aminobiphenyl caused bladder tumors in rabbits and dogs and dose-related incidences of angiosarcoma (blood-vessel tumors), liver tumors, and bladder tumors in mice. When administered to rats by subcutaneous injection, 4-aminobiphenyl caused mammary-gland and intestinal tumors (IARC 1987).
Mainstream cigarette smoke was reported to contain 4-aminobiphenyl at levels of 2.4 to 4.6 ng per cigarette (unfiltered) and 0.2 to 23 ng per cigarette (filtered), and sidestream
smoke to contain up to 140 ng per cigarette (Patrianakos and Hoffmann 1979, Hoffman et al. 1997).
Health Factors
In a case-control study, levels of 4-aminobiphenyl hemoglobin adducts were higher in smokers with bladder cancer than in a control group of similarly exposed smokers (Del Santo et al. 1991). A Taiwanese study reported that 4-aminobiphenyl hemoglobin adducts were associated with increased risk of liver cancer (Wang et al. 1998).
There is sufficient evidence for the carcinogenicity of 4- aminobiphenyl in experimental animals as demonstrated by studies showing that 4-aminobiphenyl causes cancer in rats, mice, rabbits, and dogs. When administered orally, 4-aminobiphenyl caused bladder tumors in rabbits and dogs and dose-related incidences of angiosarcoma (blood-vessel tumors), liver tumors, and bladder tumors in mice. When administered to rats by subcutaneous injection, 4-aminobiphenyl caused mammary-gland and intestinal tumors (IARC 1987).
Mainstream cigarette smoke was reported to contain 4-aminobiphenyl at levels of 2.4 to 4.6 ng per cigarette (unfiltered) and 0.2 to 23 ng per cigarette (filtered), and sidestream
smoke to contain up to 140 ng per cigarette (Patrianakos and Hoffmann 1979, Hoffman et al. 1997).
Health Factors
NTP: Human Carcinogen
IARC: Group 1, carcinogenic to humans (4-Aminobiphenyl)
SYMPTOM(s): Headaches, lethargy, dizziness; dyspnea; ataxia, weakness; methemoglobinemia; urinary burning; acute hemorrhage cystitis, (carcinogenic)
HEALTH EFFECTS: Cancer---Currently regulated by OSHA as carcinogen; chiefly work practice standards (HE1) LD50 (oral, rat) 500 mg/kg
SKIN ABS: Yes
SKIN ABS: Yes
ORGAN: Bladder, skin
http://www.osha.gov/dts/chemicalsampling/data/CH_218100.html
Detection limits are 10.5 fg/injection . These are the amounts of each analyte that will produce peaks with heights that are approximately five times the baseline noise.
The dose-response relationship for 4-Aminobiphenyl is sigmoidal or hockey-stick shaped. That is, responses are seen at the higher levels. For example, incidences of angiosarcomas and liver tumors were significantly higher at the three highest level doses when mice were treated with drinking water contaminated with 4-Aminobiphenyl.
Recent information is becoming available also that 4-Aminobiphenyl can also contribute to breast cancer. A recent study done in 2003 showed that smoking is associated with increased levels of 4-ABP–DNA adducts in human mammary tissue, or increased risk of breast cancer. (Faraglia et all, 2003)
References
Del Santo, P., G. Moneti, M. Salvadori, C. Saltutti, A. Delle Rose and P. Dolara. 1991. Levels of the adducts of 4-aminobiphenyl to hemoglobin in control subjects and bladder carcinoma patients. Cancer Lett 60(3): 245-51.
Detection limits are 10.5 fg/injection . These are the amounts of each analyte that will produce peaks with heights that are approximately five times the baseline noise.
The dose-response relationship for 4-Aminobiphenyl is sigmoidal or hockey-stick shaped. That is, responses are seen at the higher levels. For example, incidences of angiosarcomas and liver tumors were significantly higher at the three highest level doses when mice were treated with drinking water contaminated with 4-Aminobiphenyl.
Recent information is becoming available also that 4-Aminobiphenyl can also contribute to breast cancer. A recent study done in 2003 showed that smoking is associated with increased levels of 4-ABP–DNA adducts in human mammary tissue, or increased risk of breast cancer. (Faraglia et all, 2003)
References
Del Santo, P., G. Moneti, M. Salvadori, C. Saltutti, A. Delle Rose and P. Dolara. 1991. Levels of the adducts of 4-aminobiphenyl to hemoglobin in control subjects and bladder carcinoma patients. Cancer Lett 60(3): 245-51.
Evaluation of 4-aminobiphenyl-DNA adducts in human breast cancer: the influence of tobacco smoke, Beatrice Faraglia, Shu Yuan Chen, Marilie D. Gammon, Yujing Zhang, Susan L. Teitelbaum, Alfred I. Neugut, Habibul Ahsan, Gail C. Garbowski, Hanina Hibshoosh, Dongxin Lin, Fred F. Kadlubar and Regina M. Santella, Carcinogenesis, Vol. 24, No. 4, 719-725, April 2003 Oxford University Press.
Feng, Z., W. Hu, W. N. Rom, F. A. Beland and M. S. Tang. 2002. 4-aminobiphenyl is a major etiological agent of human bladder cancer: evidence from its DNA binding spectrum in human p53 gene Carcinogenesis 23(10): 1721-7.
IARC. 1987. Overall Evaluations of Carcinogenicity. IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Humans, Supplement 7. Lyon, France: International Agency for Research on Cancer. 440 pp.
Wang, L. Y., C. J. Chen, Y. J. Zhang, W. Y. Tsai, P. H. Lee, M. A. Feitelson, C. S. Lee and R. M. Santella,1998. 4-Aminobiphenyl DNA damage in liver tissue of hepatocellular carcinoma patients and controls. Am J Epidemiol 147(3): 315-23.
IARC. 1987. Overall Evaluations of Carcinogenicity. IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Humans, Supplement 7. Lyon, France: International Agency for Research on Cancer. 440 pp.
Wang, L. Y., C. J. Chen, Y. J. Zhang, W. Y. Tsai, P. H. Lee, M. A. Feitelson, C. S. Lee and R. M. Santella,1998. 4-Aminobiphenyl DNA damage in liver tissue of hepatocellular carcinoma patients and controls. Am J Epidemiol 147(3): 315-23.
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