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Volumn 10, Issue 11, 1997, Pages 1275-1284

Covalent DNA adducts formed by benzo[c]chrysene in mouse epidermis and by benzo[c]chrysene fjord-region diol epoxides reacted with DNA and polynucleotides

Author keywords

[No Author keywords available]

Indexed keywords

CHRYSENE DERIVATIVE; EPOXIDE; POLYCYCLIC AROMATIC HYDROCARBON; POLYNUCLEOTIDE;

EID: 0030734878     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970114x     Document Type: Article
Times cited : (13)

References (44)
  • 1
    • 0002624809 scopus 로고
    • Polynuclear aromatic carcinogens
    • Searle, C. E., Ed., American Chemical Society, Washington, DC
    • Dipple, A., Moschel, R. C., and Bigger, C. A. H. (1984) Polynuclear aromatic carcinogens. In Chemical Carcinogens, 2nd ed. (Searle, C. E., Ed.) pp 41-163, American Chemical Society, Washington, DC.
    • (1984) Chemical Carcinogens, 2nd Ed , pp. 41-163
    • Dipple, A.1    Moschel, R.C.2    Bigger, C.A.H.3
  • 3
    • 0002124690 scopus 로고
    • Stereoselective biotransformation of polycyclic aromatic hydrocarbons to ultimate carcinogens
    • Wainer, A. W., and Dryer, D. Eds., Marcel Dekker, New York
    • Thakker, D. R., Levin, W., Yagi, H., Wood, A. W., Conney, A. H., and Jerina, D. M. (1988) Stereoselective biotransformation of polycyclic aromatic hydrocarbons to ultimate carcinogens. In Stereochemical Aspects of Pharmacologically Active Compounds (Wainer, A. W., and Dryer, D. Eds.) pp 271-296, Marcel Dekker, New York.
    • (1988) Stereochemical Aspects of Pharmacologically Active Compounds , pp. 271-296
    • Thakker, D.R.1    Levin, W.2    Yagi, H.3    Wood, A.W.4    Conney, A.H.5    Jerina, D.M.6
  • 4
    • 0025941641 scopus 로고
    • Covalent bonding of bay region diol epoxides to nucleic acids
    • Witmer, C. M., Snyder, R., Jollow, D. J., Kalf, G. F., Koscis, J. J., and Sipes, I. G., Eds., Plenum Press: New York
    • Jerina, D. M., Chadha, A., Cheh, A. M., Schurdak, M. E., Wood, A. W., and Sayer, J. M. (1991) Covalent bonding of bay region diol epoxides to nucleic acids. In Biological Reactive Intermediates IV (Witmer, C. M., Snyder, R., Jollow, D. J., Kalf, G. F., Koscis, J. J., and Sipes, I. G., Eds.) pp 533-553, Plenum Press: New York.
    • (1991) Biological Reactive Intermediates IV , pp. 533-553
    • Jerina, D.M.1    Chadha, A.2    Cheh, A.M.3    Schurdak, M.E.4    Wood, A.W.5    Sayer, J.M.6
  • 5
    • 0029007324 scopus 로고
    • Quantum mechanical studies of the structure and reactivities of the diol epoxides of benzo[c]phenanthrene
    • Lewisbevan, L., Little, S. B., and Rabinowitz, J. R. (1995) Quantum mechanical studies of the structure and reactivities of the diol epoxides of benzo[c]phenanthrene. Chem. Res. Toxicol. 8, 499-505.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 499-505
    • Lewisbevan, L.1    Little, S.B.2    Rabinowitz, J.R.3
  • 6
    • 0022607674 scopus 로고
    • Tumorigenicity of optical isomers of the diastereomeric bay region 3,4-diol 1,2-epoxides of benzo[c]phenanthrene in murine tumor models
    • Levin, W., Chang, R. L., Wood, A. W., Thakker, R. D., Yagi, H., Jerina, D. M., and Conney, A. H. (1986) Tumorigenicity of optical isomers of the diastereomeric bay region 3,4-diol 1,2-epoxides of benzo[c]phenanthrene in murine tumor models. Cancer Res. 46, 2257-2261.
    • (1986) Cancer Res , vol.46 , pp. 2257-2261
    • Levin, W.1    Chang, R.L.2    Wood, A.W.3    Thakker, R.D.4    Yagi, H.5    Jerina, D.M.6    Conney, A.H.7
  • 7
    • 0023479266 scopus 로고
    • Role of diaxial versus diequatorial hydroxyl groups in the tumorigenic activity of a benzo[a]pyrene bay region diol epoxide
    • Chang, R. L., Wood, A. W., Conney, A. H., Yagi, H., Sayer, J. M., Thakker, D. R., Jerina, D. M., and Levin, W. (1987) Role of diaxial versus diequatorial hydroxyl groups in the tumorigenic activity of a benzo[a]pyrene bay region diol epoxide. Proc. Natl. Acad. Sci. U.S.A. 84, 8633-8636.
    • (1987) Proc. Natl. Acad. Sci. U.S.A. , vol.84 , pp. 8633-8636
    • Chang, R.L.1    Wood, A.W.2    Conney, A.H.3    Yagi, H.4    Sayer, J.M.5    Thakker, D.R.6    Jerina, D.M.7    Levin, W.8
  • 8
    • 0023230901 scopus 로고
    • Stereochemical specificity in the metabolic activation of benzo[c]phenanthrene to metabolites that covalently bind to DNA in rodent embryo cell cultures
    • Pruess-Schwartz, D., Baird, W. M., Yagi, H., Jerina, D. M., Pigott, M. A., and Dipple, A. (1987) Stereochemical specificity in the metabolic activation of benzo[c]phenanthrene to metabolites that covalently bind to DNA in rodent embryo cell cultures. Cancer Res. 47, 4032-4037.
    • (1987) Cancer Res , vol.47 , pp. 4032-4037
    • Pruess-Schwartz, D.1    Baird, W.M.2    Yagi, H.3    Jerina, D.M.4    Pigott, M.A.5    Dipple, A.6
  • 9
    • 0022998477 scopus 로고
    • Stereo-selective metabolism of the (+)-(S,S) and (-)-(R,R)-enantiomers of trans-3,4-dihydroxy-3,4-dihydrobenzo[c]phenanthrene by rat and mouse liver microsomes and by a purified and reconstituted cytochrome P-450 system
    • Thakker, D. R., Levin, W., Yagi, H., Yeh, H. J. C., Ryan, D. E., Thomas, P. E., Conney, A. H., and Jerina, D. M. (1986) Stereo-selective metabolism of the (+)-(S,S) and (-)-(R,R)-enantiomers of trans-3,4-dihydroxy-3,4-dihydrobenzo[c]phenanthrene by rat and mouse liver microsomes and by a purified and reconstituted cytochrome P-450 system. J. Biol. Chem. 261, 5404-5413.
    • (1986) J. Biol. Chem. , vol.261 , pp. 5404-5413
    • Thakker, D.R.1    Levin, W.2    Yagi, H.3    Yeh, H.J.C.4    Ryan, D.E.5    Thomas, P.E.6    Conney, A.H.7    Jerina, D.M.8
  • 10
    • 0029888071 scopus 로고    scopus 로고
    • Covalent DNA adducts formed in mouse epidermis by benzo[g]chrysene
    • Giles, A. S., Seidel, A., and Phillips, D. H. (1996) Covalent DNA adducts formed in mouse epidermis by benzo[g]chrysene. Carcinogenesis 17, 1331-1336.
    • (1996) Carcinogenesis , vol.17 , pp. 1331-1336
    • Giles, A.S.1    Seidel, A.2    Phillips, D.H.3
  • 11
    • 0021287601 scopus 로고
    • Mutagenicity of the enantiomers of the diastereomeric bay region benzo[c]-phenanthrene 3,4-diol-1,2-epoxides in bacterial and mammalian cells
    • Wood, A. W., Chang, R. L., Levin, W., Thakker, D. R., Yagi, H., Sayer, J. M., Jerina, D. M., and Conney, A. H. (1984) Mutagenicity of the enantiomers of the diastereomeric bay region benzo[c]-phenanthrene 3,4-diol-1,2-epoxides in bacterial and mammalian cells. Cancer Res. 44, 2320-2324.
    • (1984) Cancer Res , vol.44 , pp. 2320-2324
    • Wood, A.W.1    Chang, R.L.2    Levin, W.3    Thakker, D.R.4    Yagi, H.5    Sayer, J.M.6    Jerina, D.M.7    Conney, A.H.8
  • 12
    • 0018928561 scopus 로고
    • Exceptionally high tumor-initiating activity of benzo[c]phenanthrene bay region diol epoxides on mouse skin
    • Levin, W., Wood, A. W., Chang, R. L., Ittah, Y., Croisy-Delcey, M., Yagi, H., Jerina, D. M., and Conney, A. H. (1980) Exceptionally high tumor-initiating activity of benzo[c]phenanthrene bay region diol epoxides on mouse skin. Cancer Res. 40, 3910-3914.
    • (1980) Cancer Res , vol.40 , pp. 3910-3914
    • Levin, W.1    Wood, A.W.2    Chang, R.L.3    Ittah, Y.4    Croisy-Delcey, M.5    Yagi, H.6    Jerina, D.M.7    Conney, A.H.8
  • 14
    • 0000867867 scopus 로고
    • Survey of compounds which have been tested for carcinogenic activity
    • Superintendent of Documents, U.S. Government Printing Office, Washington, DC
    • Hartwell, J. L. (1951) Survey of compounds which have been tested for carcinogenic activity. U.S. Public Health Service Publication No. 149, Superintendent of Documents, U.S. Government Printing Office, Washington, DC.
    • (1951) U.S. Public Health Service Publication No. 149 , vol.149
    • Hartwell, J.L.1
  • 15
    • 0025729033 scopus 로고
    • Fjord and bay region diol epoxides investigated for stability, SOS induction in Esherichia coli and mutagenicity in Salmonella typhimurium and mammalian cells
    • Glatt, H., Piee, A., Pauly, K., Steinbrecher, T., Schrode, R., Oesch, F., and Seidel, A. (1991) Fjord and bay region diol epoxides investigated for stability, SOS induction in Esherichia coli and mutagenicity in Salmonella typhimurium and mammalian cells. Cancer Res. 51, 1659-1667.
    • (1991) Cancer Res , vol.51 , pp. 1659-1667
    • Glatt, H.1    Piee, A.2    Pauly, K.3    Steinbrecher, T.4    Schrode, R.5    Oesch, F.6    Seidel, A.7
  • 16
    • 0025948227 scopus 로고
    • Relationship between mutagenicity and DNA adduct formation in mammalian cells for fjord and bay region diol epoxides of polycyclic aromatic hydrocarbons
    • Phillips, D. H., Hewer, A., Seidel, A., Steinbrecher, T., Schrode, R., Oesch, F., and Glatt, H. (1991) Relationship between mutagenicity and DNA adduct formation in mammalian cells for fjord and bay region diol epoxides of polycyclic aromatic hydrocarbons. Chem.-Biol. Interact. 80, 177-186.
    • (1991) Chem.-Biol. Interact. , vol.80 , pp. 177-186
    • Phillips, D.H.1    Hewer, A.2    Seidel, A.3    Steinbrecher, T.4    Schrode, R.5    Oesch, F.6    Glatt, H.7
  • 17
    • 0000960731 scopus 로고
    • Synthesis of optically active fjord-region 11,12-diol 13,14-epoxides and the K region 9,10-oxide of the carcinogen benzo[g]-chrysene
    • Bushman, D. R., Grossman, S. J., Jerina, D. M., and Lehr, R. E. (1989) Synthesis of optically active fjord-region 11,12-diol 13,14-epoxides and the K region 9,10-oxide of the carcinogen benzo[g]-chrysene. J. Org. Chem. 54, 3533-3544.
    • (1989) J. Org. Chem. , vol.54 , pp. 3533-3544
    • Bushman, D.R.1    Grossman, S.J.2    Jerina, D.M.3    Lehr, R.E.4
  • 18
    • 33845551079 scopus 로고
    • Efficient synthesis of non-K region dihydrodiols of polycyclic aromatic hydrocarbons from o-quinones and catechols
    • Platt, K. L., and Oesch, F. (1983) Efficient synthesis of non-K region dihydrodiols of polycyclic aromatic hydrocarbons from o-quinones and catechols. J. Org. Chem. 48, 256-268.
    • (1983) J. Org. Chem. , vol.48 , pp. 256-268
    • Platt, K.L.1    Oesch, F.2
  • 19
    • 0001610152 scopus 로고
    • Synthesis and assignment of absolute configuration to the trans-3,4-dihydrodiols and 3,4-diol-1,2-epoxides of benzo-[c]phenanthrene
    • Yagi, H., Thakker, D. R., Ittah, Y., Croisy-Delcey, M., and Jerina, D. M. (1983) Synthesis and assignment of absolute configuration to the trans-3,4-dihydrodiols and 3,4-diol-1,2-epoxides of benzo-[c]phenanthrene. Tetrahedron Lett. 24, 1349-1352.
    • (1983) Tetrahedron Lett , vol.24 , pp. 1349-1352
    • Yagi, H.1    Thakker, D.R.2    Ittah, Y.3    Croisy-Delcey, M.4    Jerina, D.M.5
  • 20
    • 0018136828 scopus 로고
    • The covalent binding of polycyclic hydrocarbons to DNA in the skin of mice of different strains
    • Phillips, D. H., Grover, P. L., and Sims, P. (1978) The covalent binding of polycyclic hydrocarbons to DNA in the skin of mice of different strains. Int. J. Cancer 22, 487-494.
    • (1978) Int. J. Cancer , vol.22 , pp. 487-494
    • Phillips, D.H.1    Grover, P.L.2    Sims, P.3
  • 21
    • 0000530035 scopus 로고
    • Nonrandom binding of the carcinogen N-hyydroxy-2-acetylaminofluorene to repetitive sequences of rat liver DNA in vivo
    • Gupta, R. C. (1984) Nonrandom binding of the carcinogen N-hyydroxy-2-acetylaminofluorene to repetitive sequences of rat liver DNA in vivo. Proc. Natl. Acad. Sci. U.S.A. 81, 6943-6947.
    • (1984) Proc. Natl. Acad. Sci. U.S.A. , vol.81 , pp. 6943-6947
    • Gupta, R.C.1
  • 22
    • 0022774562 scopus 로고
    • 32P-postlabeling test for structurally diverse DNA adducts
    • 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis 7, 1543-1551.
    • (1986) Carcinogenesis , vol.7 , pp. 1543-1551
    • Reddy, M.V.1    Randerath, K.2
  • 23
    • 0020334611 scopus 로고
    • 32P-Postlabeling analysis of nonradioactive aromatic carcinogen-DNA adducts
    • 32P-Postlabeling analysis of nonradioactive aromatic carcinogen-DNA adducts. Carcinogenesis 3, 1081-1092.
    • (1982) Carcinogenesis , vol.3 , pp. 1081-1092
    • Gupta, R.C.1    Reddy, M.V.2    Randerath, K.3
  • 25
    • 0025895966 scopus 로고
    • 32P-postlabeled nucleoside 3′,5′-bisphosphate adducts of polycyclic aromatic hydrocarbons
    • 32P-postlabeled nucleoside 3′,5′-bisphosphate adducts of polycyclic aromatic hydrocarbons. J. Chromatogr. 570, 65-76.
    • (1991) J. Chromatogr. , vol.570 , pp. 65-76
    • Pfau, W.1    Phillips, D.H.2
  • 26
    • 37049045997 scopus 로고
    • Evidence for the binding of polynuclear aromatic hydrocarbons to the nucleic acids of mouse skin: Relation between carcinogenic power of hydrocarbons and their binding to deoxyribonucleic acid
    • Brookes, P., and Lawley, P. D. (1964) Evidence for the binding of polynuclear aromatic hydrocarbons to the nucleic acids of mouse skin: relation between carcinogenic power of hydrocarbons and their binding to deoxyribonucleic acid. Nature (London) 202, 781-784.
    • (1964) Nature (London) , vol.202 , pp. 781-784
    • Brookes, P.1    Lawley, P.D.2
  • 27
    • 0031044646 scopus 로고    scopus 로고
    • Metabolic activation of benzo[g]-chrysene in the human mammary carcinoma cell line MCF-7
    • Agarwal, R., Coffing, S. L., Baird, W. M., Kiselyov, A. S., Harvey, R. G., and Dipple, A. (1997) Metabolic activation of benzo[g]-chrysene in the human mammary carcinoma cell line MCF-7. Cancer Res. 57, 415-419.
    • (1997) Cancer Res , vol.57 , pp. 415-419
    • Agarwal, R.1    Coffing, S.L.2    Baird, W.M.3    Kiselyov, A.S.4    Harvey, R.G.5    Dipple, A.6
  • 28
    • 0029608787 scopus 로고
    • Stereoselective activation of dibenzo[a,l]pyrene to (-)-anti (11R,12S,13S,14R)- And (+)-syn (11S,12R,13S,14R)-11,12-diol-13,-14-epoxides which bind extensively to deoxyadenosine residues of DNA in the human mammary carcinoma cell line MCF-7
    • Ralston, S. L., Seidel, A., Luch, A., Platt, K. L., and Baird, W. M. (1995) Stereoselective activation of dibenzo[a,l]pyrene to (-)-anti (11R,12S,13S,14R)- and (+)-syn (11S,12R,13S,14R)-11,12-diol-13,-14-epoxides which bind extensively to deoxyadenosine residues of DNA in the human mammary carcinoma cell line MCF-7. Carcinogenesis 16, 2899-2907.
    • (1995) Carcinogenesis , vol.16 , pp. 2899-2907
    • Ralston, S.L.1    Seidel, A.2    Luch, A.3    Platt, K.L.4    Baird, W.M.5
  • 29
    • 0024591163 scopus 로고
    • Absolute stereochemistry of the major 7,12-dimethylbenz[a]anthracene-DNA adducts formed in mouse cells
    • Vericat, J. A., Cheng, S. C., and Dipple, A. (1989) Absolute stereochemistry of the major 7,12-dimethylbenz[a]anthracene-DNA adducts formed in mouse cells. Carcinogenesis 10, 567-570.
    • (1989) Carcinogenesis , vol.10 , pp. 567-570
    • Vericat, J.A.1    Cheng, S.C.2    Dipple, A.3
  • 31
    • 0026661470 scopus 로고
    • Metabolic activation of carcinogens
    • Guengerich, F. P. (1992) Metabolic activation of carcinogens. Pharmacol. Ther. 54, 17-61.
    • (1992) Pharmacol. Ther. , vol.54 , pp. 17-61
    • Guengerich, F.P.1
  • 32
    • 0028826889 scopus 로고
    • Cytochromes CYP1A1 and CYP1B1 in the rat mammary gland: Cell-specific expression and regulation by polycyclic aromatic hydrocarbons and hormones
    • Christou, M., Savas, U., Schroeder, S., Shen, X., Thompson, T., Gould, M. N., and Jefcoate, C. R. (1995) Cytochromes CYP1A1 and CYP1B1 in the rat mammary gland: cell-specific expression and regulation by polycyclic aromatic hydrocarbons and hormones. Mol. Cell. Endocrinol. 115, 41-50.
    • (1995) Mol. Cell. Endocrinol. , vol.115 , pp. 41-50
    • Christou, M.1    Savas, U.2    Schroeder, S.3    Shen, X.4    Thompson, T.5    Gould, M.N.6    Jefcoate, C.R.7
  • 34
    • 0029824917 scopus 로고    scopus 로고
    • Benzo[c]phenanthrene is activated to DNA-binding diol epoxides in the human mammary carcinoma cell line MCF-7 but only limited activation occurs in mouse skin
    • Einolf, H. J., Amin, S., Yagi, H., Jerina, D. M., and Baird, W. M. (1996) Benzo[c]phenanthrene is activated to DNA-binding diol epoxides in the human mammary carcinoma cell line MCF-7 but only limited activation occurs in mouse skin. Carcinogenesis 17, 2237-2244.
    • (1996) Carcinogenesis , vol.17 , pp. 2237-2244
    • Einolf, H.J.1    Amin, S.2    Yagi, H.3    Jerina, D.M.4    Baird, W.M.5
  • 35
    • 0027532252 scopus 로고
    • Evidence for the involvement of a bis-diol epoxide in the metabolic activation of dibenz[a,h]anthracene to DNA-binding species in mouse skin
    • Carmichael, P. L., Platt, K. L-, Ni Shé, M., Lecoq, S., Oesch, F., Phillips, D. H., and Grover, P. L. (1993) Evidence for the involvement of a bis-diol epoxide in the metabolic activation of dibenz[a,h]anthracene to DNA-binding species in mouse skin. Cancer Res. 53, 944-948.
    • (1993) Cancer Res , vol.53 , pp. 944-948
    • Carmichael, P.L.1    Platt, K.L.2    Ni Shé, M.3    Lecoq, S.4    Oesch, F.5    Phillips, D.H.6    Grover, P.L.7
  • 36
    • 0023236470 scopus 로고
    • Optically active benzo[c]phenanthrene diol epoxides bind extensively to adenine in DNA
    • Dipple, A., Pigott, M. A., Agarwal, S. K., Yagi, H., Sayer, J. M., and Jerina, D. M. (1987) Optically active benzo[c]phenanthrene diol epoxides bind extensively to adenine in DNA. Nature (London) 327, 535-536.
    • (1987) Nature (London) , vol.327 , pp. 535-536
    • Dipple, A.1    Pigott, M.A.2    Agarwal, S.K.3    Yagi, H.4    Sayer, J.M.5    Jerina, D.M.6
  • 39
    • 0026524581 scopus 로고
    • Dimethylchrysenediol epoxides: Mutagenicity in Salmonella typhimurium, tumorigenicity in newborn mice, and reactivity with deoxyadenosine in DNA
    • Misra, B., Amin, S., and Hecht, S. S. (1992) Dimethylchrysenediol epoxides: Mutagenicity in Salmonella typhimurium, tumorigenicity in newborn mice, and reactivity with deoxyadenosine in DNA. Chem. Res. Toxicol. 5, 248-254.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 248-254
    • Misra, B.1    Amin, S.2    Hecht, S.S.3
  • 41
    • 0028793872 scopus 로고
    • Activating mutations in human c-Ha-ras-1 protooncogene induced by stereoisomeric fjord-region benzo[c]chrysene
    • Du, M.-Q., Seidel, A., and Phillips, D. H. (1995) Activating mutations in human c-Ha-ras-1 protooncogene induced by stereoisomeric fjord-region benzo[c]chrysene. Mol. Carcinogen. 14, 160-169.
    • (1995) Mol. Carcinogen. , vol.14 , pp. 160-169
    • Du, M.-Q.1    Seidel, A.2    Phillips, D.H.3
  • 42
    • 0018764876 scopus 로고
    • Covalent binding of polycyclic aromatic hydrocarbons to adenine correlates with tumorigenesis in mouse skin
    • DiGiovanni, J., Romson, J. R., Linville, D., Juchau, M. R., and Slaga, T. J. (1979) Covalent binding of polycyclic aromatic hydrocarbons to adenine correlates with tumorigenesis in mouse skin. Cancer Lett. 7, 39-43.
    • (1979) Cancer Lett , vol.7 , pp. 39-43
    • Digiovanni, J.1    Romson, J.R.2    Linville, D.3    Juchau, M.R.4    Slaga, T.J.5
  • 43
    • 0022539345 scopus 로고
    • Correlation between formation of a specific hydrocarbon-deoxyribonucleoside adduct and tumor-initiating activity of 7,12-dimethylbenz[a]-anthracene and its 9- And 10-monofluoroderivatives in mice
    • DiGiovanni, J., Sawyer, T. W., and Fisher, E. P. (1986) Correlation between formation of a specific hydrocarbon-deoxyribonucleoside adduct and tumor-initiating activity of 7,12-dimethylbenz[a]-anthracene and its 9- and 10-monofluoroderivatives in mice. Cancer Res. 46, 4336-4341.
    • (1986) Cancer Res , vol.46 , pp. 4336-4341
    • DiGiovanni, J.1    Sawyer, T.W.2    Fisher, E.P.3
  • 44
    • 0029981532 scopus 로고    scopus 로고
    • Benzolejphenanthrene-DNA adducts in mouse epidermis in relation to the tumorigenicities of four configurationally isomeric 3,4-dihydrodiol 1,2-epoxides
    • Agarwal, R., Canella, K. A., Yagi, H., Jerina, D. M., and Dipple, A. (1996) Benzolejphenanthrene-DNA adducts in mouse epidermis in relation to the tumorigenicities of four configurationally isomeric 3,4-dihydrodiol 1,2-epoxides. Chem. Res. Toxicol. 9, 586-592.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 586-592
    • Agarwal, R.1    Canella, K.A.2    Yagi, H.3    Jerina, D.M.4    Dipple, A.5


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