메뉴 건너뛰기




Volumn 17, Issue 5, 2004, Pages 672-678

Comparative metabolism of the aza polynuclear aromatic hydrocarbon dibenz[a,h]acridine by recombinant human and rat cytochrome P450s

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 1B1; CYTOCHROME P450 3A4; DIBENZ[A,H]ACRIDINE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

EID: 2442656592     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049979i     Document Type: Article
Times cited : (9)

References (45)
  • 1
    • 70449550646 scopus 로고
    • The quantitative composition of air pollution: Source of effluents in terms of aza heterocyclic compounds and polynuclear aromatic hydrocarbons
    • Sawicki, E., Meeker, J. E., and Morgan, M. J. (1965) The quantitative composition of air pollution: source of effluents in terms of aza heterocyclic compounds and polynuclear aromatic hydrocarbons. Int. J. Air Water Pollut. 9, 291-298.
    • (1965) Int. J. Air Water Pollut. , vol.9 , pp. 291-298
    • Sawicki, E.1    Meeker, J.E.2    Morgan, M.J.3
  • 2
    • 0342806193 scopus 로고
    • Organic particulate pollutants: Chemical analysis and bioassay for carcinogenicity
    • (Stern, A. C., Ed.) 3rd ed., Academic Press, New York
    • Hoffmann, D., and Wynder, E. L. (1977) Organic particulate pollutants: chemical analysis and bioassay for carcinogenicity. In Air Pollution (Stern, A. C., Ed.) 3rd ed., Vol. 2, pp 361-455, Academic Press, New York.
    • (1977) Air Pollution , vol.2 , pp. 361-455
    • Hoffmann, D.1    Wynder, E.L.2
  • 3
    • 0017401901 scopus 로고
    • Nitrogen containing compounds in tobacco and tobacco smoke
    • Schmeltz, I., and Hoffmann, D. (1977) Nitrogen containing compounds in tobacco and tobacco smoke. Chem. Rev. 77, 295-311.
    • (1977) Chem. Rev. , vol.77 , pp. 295-311
    • Schmeltz, I.1    Hoffmann, D.2
  • 4
    • 0002512236 scopus 로고
    • The carcinogenic nitrogen heterocyclics in cigarette-smoke condensate
    • Van Duuren, B. L., Bilbao, J. A., and Joseph, C. A. (1960) The carcinogenic nitrogen heterocyclics in cigarette-smoke condensate. J. Natl. Cancer Inst. 25, 53-61.
    • (1960) J. Natl. Cancer Inst. , vol.25 , pp. 53-61
    • Van Duuren, B.L.1    Bilbao, J.A.2    Joseph, C.A.3
  • 5
    • 0003173565 scopus 로고
    • Polynuclear aromatic compounds, Part 1
    • International Agency for Research on Cancer (1983) Polynuclear Aromatic Compounds, Part 1. IARC Monogr. Eval. Carcinog. Risk Chem. Hum. 32.
    • (1983) IARC Monogr. Eval. Carcinog. Risk Chem. Hum. , vol.32
  • 6
    • 29644445566 scopus 로고
    • Certain polynuclear aromatic hydrocarbons and heterocyclic compounds
    • International Agency for Research on Cancer (1972) Certain Polynuclear Aromatic Hydrocarbons and Heterocyclic Compounds. IARC Monogr. Eval. Carcinog. Risk Chem. Hum. 3.
    • (1972) IARC Monogr. Eval. Carcinog. Risk Chem. Hum. , vol.3
  • 7
    • 0007153920 scopus 로고
    • Aza-arenes in the respiratory environment: Analysis and assays for mutangenicity
    • (Jones, P. W., and Freudenthal, R. I., Eds.), Raven Press, New York
    • Dong, M., Schmelz, I., LaVoie, E., and Hoffmann, D. (1978) Aza-arenes in the respiratory environment: analysis and assays for mutangenicity. In Carcinogenesis, Vol. 3, Polynuclear Aromatic Hydrocarbons (Jones, P. W., and Freudenthal, R. I., Eds.) pp 97-108, Raven Press, New York.
    • (1978) Carcinogenesis, Vol. 3, Polynuclear Aromatic Hydrocarbons , vol.3 , pp. 97-108
    • Dong, M.1    Schmelz, I.2    LaVoie, E.3    Hoffmann, D.4
  • 8
    • 0002624809 scopus 로고
    • Polycyclic aromatic carcinogens
    • (Searle, C. E., Ed.) 2nd ed., American Chemical Society, Washington, DC
    • Dipple, A., Moschel, R. C., and Bigger, A. H. (1984) Polycyclic aromatic carcinogens. In Chemical Carcinogens (Searle, C. E., Ed.) 2nd ed., pp 43-163, American Chemical Society, Washington, DC.
    • (1984) Chemical Carcinogens , pp. 43-163
    • Dipple, A.1    Moschel, R.C.2    Bigger, A.H.3
  • 9
    • 0024819101 scopus 로고
    • Mutagenicity of dihydrodiols and diol epoxides of dibenz[a,h]acridine in bacterial and mammalian cells
    • Wood, A. W., Chang, R. L., Katz, M., Conney, A. H., Jerina, D. M., Sikka, H. C., Levin, W., and Kumar, S. (1989) Mutagenicity of dihydrodiols and diol epoxides of dibenz[a,h]acridine in bacterial and mammalian cells. Cancer Res. 49, 6981-6984.
    • (1989) Cancer Res. , vol.49 , pp. 6981-6984
    • Wood, A.W.1    Chang, R.L.2    Katz, M.3    Conney, A.H.4    Jerina, D.M.5    Sikka, H.C.6    Levin, W.7    Kumar, S.8
  • 10
    • 0034985240 scopus 로고    scopus 로고
    • Turorigenicity of racemic and optically pure bay region diol epoxides and other derivatives of the nitrogen heterocycle dibenz [a,h] acridine on mouse skin
    • Kumar, S., Chang, R. L., Wood, A. W., Xie, J. G., Huang, M. T., Cui, X. X., Kole, P. L., Sikka, H. C., Balani, S. K., Conney, A. H., and Jerina, D. M. (2001) Turorigenicity of racemic and optically pure bay region diol epoxides and other derivatives of the nitrogen heterocycle dibenz [a,h] acridine on mouse skin. Carcinogenesis 22, 951-955.
    • (2001) Carcinogenesis , vol.22 , pp. 951-955
    • Kumar, S.1    Chang, R.L.2    Wood, A.W.3    Xie, J.G.4    Huang, M.T.5    Cui, X.X.6    Kole, P.L.7    Sikka, H.C.8    Balani, S.K.9    Conney, A.H.10    Jerina, D.M.11
  • 11
    • 2442698411 scopus 로고
    • Mutagenicity and tumorigenicity of the four optically active bay-region 3,4-diol-1,2-epoxide isomers of dibenz[a,h]anthracene
    • Chang, R. L., Levin, W., Conney, A. H., Boyd, D. R., Balani, S. K., Yagi, H., Jerina, D. M., and Wood, A. W. (1989) Mutagenicity and tumorigenicity of the four optically active bay-region 3,4-diol-1,2-epoxide isomers of dibenz[a,h]anthracene. Proc. Am. Assoc. Cancer Res. 30, 144.
    • (1989) Proc. Am. Assoc. Cancer Res. , vol.30 , pp. 144
    • Chang, R.L.1    Levin, W.2    Conney, A.H.3    Boyd, D.R.4    Balani, S.K.5    Yagi, H.6    Jerina, D.M.7    Wood, A.W.8
  • 12
    • 84921178545 scopus 로고
    • Biologic testing of carcinogens. II. Pulmonary tumor induction technique
    • Andervont, H. B., and Shimkin, M. B. (1940) Biologic testing of carcinogens, II. Pulmonary tumor induction technique. J. Natl. Cancer Inst. 1, 225-239.
    • (1940) J. Natl. Cancer Inst. , vol.1 , pp. 225-239
    • Andervont, H.B.1    Shimkin, M.B.2
  • 15
    • 0033746635 scopus 로고    scopus 로고
    • Tumorigenicity of four optically active bay-region 3,4-diol 1,2-epoxides and other derivatives of the nitrogen heterocycle dibenz[c,h]acridine on mouse skin and in newborn mice
    • Chang, R. L., Wood, A. W., Kumar, S., Lehr, R. E., Naohiro, S., Jerina, D. M., and Conney, A. H. (2000) Tumorigenicity of four optically active bay-region 3,4-diol 1,2-epoxides and other derivatives of the nitrogen heterocycle dibenz[c,h]acridine on mouse skin and in newborn mice. Carcinogenesis 21, 1997-2003.
    • (2000) Carcinogenesis , vol.21 , pp. 1997-2003
    • Chang, R.L.1    Wood, A.W.2    Kumar, S.3    Lehr, R.E.4    Naohiro, S.5    Jerina, D.M.6    Conney, A.H.7
  • 16
    • 0027075963 scopus 로고
    • Environmental sources, carcinogenicity, mutagenicity, metabolism and DNA binding of nitrogen and sulfur heterocyclic aromatics
    • Warshawsky, D. (1992) Environmental sources, carcinogenicity, mutagenicity, metabolism and DNA binding of nitrogen and sulfur heterocyclic aromatics. J. Environ. Sci. Health C10, 1-71.
    • (1992) J. Environ. Sci. Health C , vol.10 , pp. 1-71
    • Warshawsky, D.1
  • 17
    • 0027333078 scopus 로고
    • Bacterial and mammalian cell mutagenicity of four optically active bay-region 10,11-diol 8,9-epoxides of the nitrogen heterocycle dibenz[a,h]acridine
    • Chang, R. L., Battista, S., Wong, C. Q., Kumar, S., Kole, P. L., Sikka, H. C., Balani, S. K., Jerina, D. M., Conney, A. H., and Wood, A. W. (1993) Bacterial and mammalian cell mutagenicity of four optically active bay-region 10,11-diol 8,9-epoxides of the nitrogen heterocycle dibenz[a,h]acridine. Carcinogenesis 14, 2233-2237.
    • (1993) Carcinogenesis , vol.14 , pp. 2233-2237
    • Chang, R.L.1    Battista, S.2    Wong, C.Q.3    Kumar, S.4    Kole, P.L.5    Sikka, H.C.6    Balani, S.K.7    Jerina, D.M.8    Conney, A.H.9    Wood, A.W.10
  • 18
    • 0023395699 scopus 로고
    • Metabolism of dibenz[a,h]acridine by rat liver microsomes
    • Steward, A. R., Kumar, S., and Sikka, H. C. (1987) Metabolism of dibenz[a,h]acridine by rat liver microsomes. Carcinogenesis 8, 1043-1050.
    • (1987) Carcinogenesis , vol.8 , pp. 1043-1050
    • Steward, A.R.1    Kumar, S.2    Sikka, H.C.3
  • 19
    • 0028969116 scopus 로고
    • Stereoselective metabolism of dibenz[a,h]acridine to bay-region diol epoxides by rat liver microsomes
    • Kumar, S., Singh, S. K., Kole, P. L., Elmarakby, S., and Sikka, H. C. (1995) Stereoselective metabolism of dibenz[a,h]acridine to bay-region diol epoxides by rat liver microsomes. Carcinogenesis 16, 525-530.
    • (1995) Carcinogenesis , vol.16 , pp. 525-530
    • Kumar, S.1    Singh, S.K.2    Kole, P.L.3    Elmarakby, S.4    Sikka, H.C.5
  • 20
    • 0002888510 scopus 로고
    • Human cytochrome P450 enzymes
    • (Ortiz de Montellano, P. R., Ed.) 2nd ed., Plenum, New York
    • Guengerich, F. P. (1995) Human cytochrome P450 enzymes. In Cytochrome P450 (Ortiz de Montellano, P. R., Ed.) 2nd ed., pp 473-535, Plenum, New York.
    • (1995) Cytochrome P450 , pp. 473-535
    • Guengerich, F.P.1
  • 21
    • 0021749950 scopus 로고
    • Binding and metabolism of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene by seven purified forms of cytochrome P-450
    • Wilson, N. M., Christou, M., Turner, C. R., Wrighton, S. A., and Jefcoate, C. R. (1984) Binding and metabolism of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene by seven purified forms of cytochrome P-450. Carcinogenesis 5, 1475-1483.
    • (1984) Carcinogenesis , vol.5 , pp. 1475-1483
    • Wilson, N.M.1    Christou, M.2    Turner, C.R.3    Wrighton, S.A.4    Jefcoate, C.R.5
  • 22
    • 0024343762 scopus 로고
    • Relative contribution of various forms of cytochrome P450 to the metabolism of benzo[a]pyrene by human liver microsomes
    • Hall, M., Forrester, L. M., Parker, D. K., Grover, P. L., and Wolf, C. R. (1989) Relative contribution of various forms of cytochrome P450 to the metabolism of benzo[a]pyrene by human liver microsomes. Carcinogenesis 10, 1815-1821.
    • (1989) Carcinogenesis , vol.10 , pp. 1815-1821
    • Hall, M.1    Forrester, L.M.2    Parker, D.K.3    Grover, P.L.4    Wolf, C.R.5
  • 23
    • 0027183516 scopus 로고
    • The catalytic activity of four expressed human cytochrome P450s towards benzo[a]pyrene and the isomers of its proximate carcinogen
    • Roberts-Thompson, S. J., McManus, M. E., Tukey, R. H., Gonzalez, F. F., and Holder, G. M. (1993) The catalytic activity of four expressed human cytochrome P450s towards benzo[a]pyrene and the isomers of its proximate carcinogen. Biochem. Biophys. Res. Commun. 192, 1373-1379.
    • (1993) Biochem. Biophys. Res. Commun. , vol.192 , pp. 1373-1379
    • Roberts-Thompson, S.J.1    McManus, M.E.2    Tukey, R.H.3    Gonzalez, F.F.4    Holder, G.M.5
  • 24
    • 0027937066 scopus 로고
    • The role of 12 cDNA-expressed human, rodent, and rabbit cytochromes P450 in the metabolism of benzo[a]pyrene and benzo[a]pyrene trans-7,8-dihydrodiol
    • Shou, M., Korzekwa, K. R., Crespi, C. L., Gonzalez, F. J., and Gelboin, H. V. (1994) The role of 12 cDNA-expressed human, rodent, and rabbit cytochromes P450 in the metabolism of benzo[a]pyrene and benzo[a]pyrene trans-7,8-dihydrodiol. Mol. Carcinog. 10, 159-168.
    • (1994) Mol. Carcinog. , vol.10 , pp. 159-168
    • Shou, M.1    Korzekwa, K.R.2    Crespi, C.L.3    Gonzalez, F.J.4    Gelboin, H.V.5
  • 26
    • 0029850968 scopus 로고    scopus 로고
    • Metabolic activation of the potent carcinogen dibenzo[a,l]pyrene by human recombinant cytochromes P450, lung and liver microsomes
    • Shou, M., Krausz, W. K., Gonzalez, F. J., and Gelboin, H. V. (1996) Metabolic activation of the potent carcinogen dibenzo[a,l]pyrene by human recombinant cytochromes P450, lung and liver microsomes. Carcinogenesis 17, 2429-2433.
    • (1996) Carcinogenesis , vol.17 , pp. 2429-2433
    • Shou, M.1    Krausz, W.K.2    Gonzalez, F.J.3    Gelboin, H.V.4
  • 27
    • 0029970205 scopus 로고    scopus 로고
    • Metabolic activation of the potent carcinogen dibenzo[a,h]anthracene by cDNA-expressed human cytochromes P450
    • Shou, M., Krausz, W. K., Gonzalez, F. J., and Gelboin, H. V. (1996) Metabolic activation of the potent carcinogen dibenzo[a,h]anthracene by cDNA-expressed human cytochromes P450. Arch. Biochem. Biophys. 328, 201-207.
    • (1996) Arch. Biochem. Biophys. , vol.328 , pp. 201-207
    • Shou, M.1    Krausz, W.K.2    Gonzalez, F.J.3    Gelboin, H.V.4
  • 30
    • 0034876318 scopus 로고    scopus 로고
    • Metabolic activation of polycyclic aromatic hydrocarbons and other procarcinogens by cytochromes P450 1A1 and P450 1B1 allelic variants and other human cytochromes P450 in Salmonella typhimurium NM2009
    • Shimada, T., Oda, Y., Gillam, E. M. J., Guengerich, F. P., and Inoue, K. (2001) Metabolic activation of polycyclic aromatic hydrocarbons and other procarcinogens by cytochromes P450 1A1 and P450 1B1 allelic variants and other human cytochromes P450 in Salmonella typhimurium NM2009. Drug Metab. Dispos. 29, 1176-1182.
    • (2001) Drug Metab. Dispos. , vol.29 , pp. 1176-1182
    • Shimada, T.1    Oda, Y.2    Gillam, E.M.J.3    Guengerich, F.P.4    Inoue, K.5
  • 31
    • 0032838774 scopus 로고    scopus 로고
    • Metabolism of benzo[a]pyrene by trans-7,8-dihyroxy-7,8-dihyrobenzo[a]pyrene by recombinant human cytochrome P450 1B1 and purified liver epoxide hydrolase
    • Shimada, T., Gillam, E. M. J., Oda, Y., Tsumura, F., Sutter, T. R., Guengerich, F. P., and Inoue, K. (1999) Metabolism of benzo[a]pyrene by trans-7,8-dihyroxy-7,8-dihyrobenzo[a]pyrene by recombinant human cytochrome P450 1B1 and purified liver epoxide hydrolase. Chem. Res. Toxicol. 12, 623-629.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 623-629
    • Shimada, T.1    Gillam, E.M.J.2    Oda, Y.3    Tsumura, F.4    Sutter, T.R.5    Guengerich, F.P.6    Inoue, K.7
  • 32
    • 0033302787 scopus 로고    scopus 로고
    • Human cytochrome P450 1B1 and chemical carcinogenesis
    • Shimada, T. (2000) Human cytochrome P450 1B1 and chemical carcinogenesis. Rev. Toxicol. 3, 139-166.
    • (2000) Rev. Toxicol. , vol.3 , pp. 139-166
    • Shimada, T.1
  • 33
    • 0018139858 scopus 로고
    • Regio- and stereoselectivity of various forms of purified cytochrome P-450 in the metabolism of benzo[a]pyrene and (-)trans-7,8-dihydroxy-7,8-dihydrobenzo [a] pyrene as shown byproduct formation and binding to DNA
    • Deutsch, J., Leutz, J. C., Yang, S. K., Gelboin, H. V., Chiang, Y. L., Vatsis, K. P., and Coon, M. J. (1978) Regio- and stereoselectivity of various forms of purified cytochrome P-450 in the metabolism of benzo[a]pyrene and (-)trans-7,8-dihydroxy-7,8-dihydrobenzo [a] pyrene as shown byproduct formation and binding to DNA. Proc. Natl. Acad. Sci. U.S.A. 75, 3123-3127.
    • (1978) Proc. Natl. Acad. Sci. U.S.A. , vol.75 , pp. 3123-3127
    • Deutsch, J.1    Leutz, J.C.2    Yang, S.K.3    Gelboin, H.V.4    Chiang, Y.L.5    Vatsis, K.P.6    Coon, M.J.7
  • 34
    • 0028085833 scopus 로고
    • Regio- and stereoselective metabolism of phenanthrene by twelve cDNA-expressed human, rodent, and rabbit cytochromes P-450
    • Shou, M., Korzekwa, K. R., Krausz, K. W., Crespi, C. L., Gonzalez, F. J., and Gelboin, H. V. (1994) Regio- and stereoselective metabolism of phenanthrene by twelve cDNA-expressed human, rodent, and rabbit cytochromes P-450. Cancer Lett. 83, 305-313.
    • (1994) Cancer Lett. , vol.83 , pp. 305-313
    • Shou, M.1    Korzekwa, K.R.2    Krausz, K.W.3    Crespi, C.L.4    Gonzalez, F.J.5    Gelboin, H.V.6
  • 35
    • 0031861991 scopus 로고    scopus 로고
    • Regio- and stereoselectivity in the metabolism of benzo[c]phenanthrene mediated by genetically engineered V79 Chinese hamster cells expressing rat and human cytochromes P450
    • Seidel, A., Soballa, V. J., Raab, G., Frank, H., Greim, H., Grimmer, G., Jacob, J., and Doehmer, J. (1998) Regio- and stereoselectivity in the metabolism of benzo[c]phenanthrene mediated by genetically engineered V79 Chinese hamster cells expressing rat and human cytochromes P450. Environ. Toxicol. Pharmacol. 5, 179-196.
    • (1998) Environ. Toxicol. Pharmacol. , vol.5 , pp. 179-196
    • Seidel, A.1    Soballa, V.J.2    Raab, G.3    Frank, H.4    Greim, H.5    Grimmer, G.6    Jacob, J.7    Doehmer, J.8
  • 36
    • 0028968440 scopus 로고
    • Metabolism of polycyclic azaaromatic carcinogens catalyzed by four expressed human cytochromes P450
    • Roberts-Thompson, S. J., McManus, M. E., Tukey, R. H., Gonzalez, F. J., and Holder, G. M. (1995) Metabolism of polycyclic azaaromatic carcinogens catalyzed by four expressed human cytochromes P450. Cancer Res. 55, 1052-1059.
    • (1995) Cancer Res. , vol.55 , pp. 1052-1059
    • Roberts-Thompson, S.J.1    McManus, M.E.2    Tukey, R.H.3    Gonzalez, F.J.4    Holder, G.M.5
  • 37
    • 0028328463 scopus 로고
    • Coexpression of CYP 1A1 and a human analogue of cytochrome P450-EF in response to 2,3,7,8-tetrachloro-dibenzo-p-dioxin in the human mammary carcinoma-derived MCF-7 cells
    • Christou, M., Savas, U., Spink, D. C., Gierthy, J. F., and Jefcoate, C. R. (1994) Coexpression of CYP 1A1 and a human analogue of cytochrome P450-EF in response to 2,3,7,8-tetrachloro-dibenzo-p-dioxin in the human mammary carcinoma-derived MCF-7 cells. Carcinogenesis 15, 725-732.
    • (1994) Carcinogenesis , vol.15 , pp. 725-732
    • Christou, M.1    Savas, U.2    Spink, D.C.3    Gierthy, J.F.4    Jefcoate, C.R.5
  • 38
    • 0021995557 scopus 로고
    • Synthesis of trans-10,11-dihydroxy-10,11-dihydrodibenz[a,h]acridine and its diastereomeric epoxides: Possible carcinogenic metabolites of dibenz[a]acridine
    • Kumar, S. (1985) Synthesis of trans-10,11-dihydroxy-10,11-dihydrodibenz[a,h]acridine and its diastereomeric epoxides: possible carcinogenic metabolites of dibenz[a]acridine. J. Org. Chem. 50, 3070-3073.
    • (1985) J. Org. Chem. , vol.50 , pp. 3070-3073
    • Kumar, S.1
  • 39
    • 0001540205 scopus 로고
    • Synthesis of dihydrodiols and diol epoxides of dibenz[a,h]acridine
    • Kumar, S., and Agarawal, N. L. (1986) Synthesis of dihydrodiols and diol epoxides of dibenz[a,h]acridine. J. Org. Chem. 51, 2445-2449.
    • (1986) J. Org. Chem. , vol.51 , pp. 2445-2449
    • Kumar, S.1    Agarawal, N.L.2
  • 40
    • 0017668828 scopus 로고
    • Radioactive assay for aryl hydrocarbon hydroxlyase. Improved method and biological importance
    • Van Cantfort, J., Degraeve, J., and Gielen, J. E. (1977) Radioactive assay for aryl hydrocarbon hydroxlyase. Improved method and biological importance. Biochem. Biophys. Res. Commun. 79, 505-512.
    • (1977) Biochem. Biophys. Res. Commun. , vol.79 , pp. 505-512
    • Van Cantfort, J.1    Degraeve, J.2    Gielen, J.E.3
  • 41
    • 0004834997 scopus 로고
    • Synthesis of enantiomerically pure bay-region 10,11-diol-8,9-epoxide diastereomers of carcinogen dibenz[a,h]acridine
    • Kumar, S., Kole, P. L., Balani, S. K., and Jerina, D. M. (1992) Synthesis of enantiomerically pure bay-region 10,11-diol-8,9-epoxide diastereomers of carcinogen dibenz[a,h]acridine. J. Org. Chem. 50, 2784-2787.
    • (1992) J. Org. Chem. , vol.50 , pp. 2784-2787
    • Kumar, S.1    Kole, P.L.2    Balani, S.K.3    Jerina, D.M.4
  • 42
    • 0002915314 scopus 로고
    • Synthesis of enatiomerically pure bay-region 3,4-diol-1,2-epoxide diastereomers and other derivatives of potent carcinogen dibenz[c,h]acridine
    • Lehr, R. E., Kumar, S., Shirai, N., and Jerina, D. M. (1985) Synthesis of enatiomerically pure bay-region 3,4-diol-1,2-epoxide diastereomers and other derivatives of potent carcinogen dibenz[c,h]acridine. J. Org. Chem. 50, 98-107.
    • (1985) J. Org. Chem. , vol.50 , pp. 98-107
    • Lehr, R.E.1    Kumar, S.2    Shirai, N.3    Jerina, D.M.4
  • 43
    • 0000547545 scopus 로고
    • Synthesis of the enantiomeric bay-region diol epoxides of benz[a]anthracene and chrysene
    • Yagi, H., Vyar, K. P., Tada, M., Thakker, D. R., and Jerina, D. M. (1982) Synthesis of the enantiomeric bay-region diol epoxides of benz[a]anthracene and chrysene. J. Org. Chem. 47, 1110-1117.
    • (1982) J. Org. Chem. , vol.47 , pp. 1110-1117
    • Yagi, H.1    Vyar, K.P.2    Tada, M.3    Thakker, D.R.4    Jerina, D.M.5
  • 44
    • 0001610152 scopus 로고
    • Synthesis and assignment of absolute configuration to the trans-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-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
  • 45
    • 0001488917 scopus 로고
    • Polycyclic aromatic hydrocarbons: Metabolic activation to ultimate carcinogens
    • (Anders, M. W., Ed.), Academic Press, New York
    • Thakker, D. R., Yagi, H., Levin, W., Wood, A. W., Conney, A. H., and Jerina, D. M. (1985) Polycyclic aromatic hydrocarbons: metabolic activation to ultimate carcinogens. In Bioactivation of Foreign Compounds (Anders, M. W., Ed.) pp 177-242, Academic Press, New York.
    • (1985) Bioactivation of Foreign Compounds , pp. 177-242
    • Thakker, D.R.1    Yagi, H.2    Levin, W.3    Wood, A.W.4    Conney, A.H.5    Jerina, D.M.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.