Comparison of DNA binding between the carcinogen 2,6-dinitrotoluene and its noncarcinogenic analog 2,6-diaminotoluene |
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| Institution: | 1. Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autonoma de Chile, Av. Pedro de Valdivia 425, Santiago, Chile;2. Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andres Bello (UNAB), Av. República 498, Santiago, Chile;1. Graduate School of Biotechnology and Bioengineering, Yuan Ze University, No. 135, Yuan-Tung Road, Chung-Li Dist., Taoyuan City 32003, Taiwan, ROC;2. Institute of Medical Biotechnology, Tzu Chi University, No. 701, Sec. 3, Zhongyang Rd. Hualien 97004, Taiwan, ROC;3. Department of Applied Chemistry and Materials Science, Fooyin University, 151 Jinxue Rd., Daliao Dist., Kaohsiung City 83102, Taiwan, ROC;4. Department of Chemical Engineering, National Taiwan University of Science and Technology, Taipei 100, Taiwan, ROC;5. Department & Graduate Institute of Chemical Engineering & Graduate Institute of Biochemical Engineering, Ming Chi University of Technology, No. 84, Gungjuan Rd. Taishan Dist., New Taipei City 24301, Taiwan, ROC;1. Research and Development Division of OSAKA SODA Co., Ltd., Amagasaki, Hyogo 660-0842, Japan;2. Graduate School of Engineering. Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan;1. Department of Chemistry, Isfahan University of Technology, Isfahan 84156-83111, Iran;2. Department of Chemistry, University of Otago, P.O. Box 56, Dunedin 9054, New Zealand;3. Department of Agricultural Biotechnology, College of Agriculture, Isfahan University of Technology, Isfahan 84156-83111, Iran;4. Faculty of Chemistry, University of Isfahan, Isfahan 81746-73441, Iran;5. Physiology and Pharmacology Department, Pasteur Institute of Iran, Tehran, P.O. Box 13164, Iran |
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| Abstract: | We used 32P-postlabelling to compare DNA binding between the potent hepatocarcinogen 2,6-dinitrotoluene and its noncarcinogenic analog 2,6-diaminotoluene. The two compounds were compared to determine whether differences in DNA binding could partly explain the differences in their carcinogenicity. Fischer-344 rats were administered 1.2 mmol/kg of a compound by single i.p. injection and examined for DNA adduct formation in the liver. Four adducts were detected following administration of 2,6-dinitrotoluene, with a total adduct yield of 13.5 adducted nucleotides per 107 nucleotides. Qualitatively identical adducts were also detected after treatment with the derivative 2-amino-6-nitrotoluene. Adduct yields from 2,6-dinitrotoluene were 30 times greater than from 2-amino-6-nitrotoluene. No adducts were observed following treatment with 2,6-diaminotoluene. 2,6-Dinitrotoluene and 2,6-diaminotoluene were also compared for qualitative differences in hepatotoxicity. 2,6-Dinitrotoluene produced extensive hemorrhagic necrosis in the liver, whereas no evidence of hepatocellular necrosis was detected following administration of the latter. The differences between the two compounds in both DNA binding and cytotoxicity were consistent with the differences in their carcinogenicity. |
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