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Volumn 17, Issue 4, 1996, Pages 829-837

Conformational studies of depurinating DNA adducts from syn-dibenzo[a,l]pyrene diolepoxide

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; EPOXIDE; GUANINE; HYDROGEN;

EID: 0029921124     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/17.4.829     Document Type: Article
Times cited : (24)

References (43)
  • 1
    • 0026002897 scopus 로고
    • Comparative dose-response tumorigenicity studies of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene, benzo[a]pyrene, and two dibenzo[a,l]pyrene dihydrodiols in mouse skin and rat mammary gland
    • Cavaliert,E.L., Higginbotham,S., RamaKrishna,N.V.S., Dcvanesan,P.D., Todorovic,R., Rogan,E.G. and Salmasi,S. (1991) Comparative dose-response tumorigenicity studies of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene, benzo[a]pyrene, and two dibenzo[a,l]pyrene dihydrodiols in mouse skin and rat mammary gland. Carcinogenesis, 12, 1939-1944.
    • (1991) Carcinogenesis , vol.12 , pp. 1939-1944
    • Cavaliert, E.L.1    Higginbotham, S.2    RamaKrishna, N.V.S.3    Dcvanesan, P.D.4    Todorovic, R.5    Rogan, E.G.6    Salmasi, S.7
  • 2
    • 0027159541 scopus 로고
    • Tumor-initiating activity and carcinogenicity of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene and benzo[a]-pyrene at low dose in mouse skin
    • Higginbotham,S., RamaKrishna,N.V.S., Johansson,S.L., Rogan,E.G. and Cavalieri,E.L., (1993) Tumor-initiating activity and carcinogenicity of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene and benzo[a]-pyrene at low dose in mouse skin. Carcinogenesis, 14, 875-878.
    • (1993) Carcinogenesis , vol.14 , pp. 875-878
    • Higginbotham, S.1    RamaKrishna, N.V.S.2    Johansson, S.L.3    Rogan, E.G.4    Cavalieri, E.L.5
  • 3
    • 0000815212 scopus 로고
    • Direct determination of dibenzo[a,l]pyrene in crude extracts of environmental samples by laser-excited Shpol'skii spectroscopy
    • Kozin,I.S., Gooijer,C. and Velthorst,N.H. (1995) Direct determination of dibenzo[a,l]pyrene in crude extracts of environmental samples by laser-excited Shpol'skii spectroscopy. Anal. Chem., 67, 1623-1626.
    • (1995) Anal. Chem. , vol.67 , pp. 1623-1626
    • Kozin, I.S.1    Gooijer, C.2    Velthorst, N.H.3
  • 4
    • 0023305989 scopus 로고
    • Indoor air sampling and mutagenicity studies of emissions from unvented coal combustion
    • Mumford,J.L.,Harris,D.B., Williams,K., Chuang,J.C. and Cooke,M (1987) Indoor air sampling and mutagenicity studies of emissions from unvented coal combustion. Environ Sci. Technol., 21, 308-311.
    • (1987) Environ Sci. Technol. , vol.21 , pp. 308-311
    • Mumford, J.L.1    Harris, D.B.2    Williams, K.3    Chuang, J.C.4    Cooke, M.5
  • 5
    • 0023522958 scopus 로고
    • Concentrations of polycyclic hydrocarbons in airborne particles in the Netherlands and their correlation with mutagenicity
    • de Raat,W.K., Kooijman,S.A.L.M. and Gielen,J.W.J. (1987) Concentrations of polycyclic hydrocarbons in airborne particles in the Netherlands and their correlation with mutagenicity. Sci. Total Environ., 66, 95-114.
    • (1987) Sci. Total Environ. , vol.66 , pp. 95-114
    • De Raat, W.K.1    Kooijman, S.A.L.M.2    Gielen, J.W.J.3
  • 6
    • 0027093718 scopus 로고
    • The approach to understanding aromatic hydrocarbon carcinogenesis. The central role of radical cations in metabolic activation
    • Cavalieri,E.L and Rogan,E.G. (1992) The approach to understanding aromatic hydrocarbon carcinogenesis. The central role of radical cations in metabolic activation. Pharmacol. Ther., 55, 183-199.
    • (1992) Pharmacol. Ther. , vol.55 , pp. 183-199
    • Cavalieri, E.L.1    Rogan, E.G.2
  • 7
    • 0029012640 scopus 로고
    • Identification and quantitation of dibenzo[a,l]pyrene-DNA adducts formed by rat liver microsomes in vitro: Preponderance of depurinating adducts
    • Li,K.-M , Todorovic,R., Rogan,E.G , Cavalieri,E.L., Ariese,F., Suh,M., Jankowiak,R. and Small,G.J (1995) Identification and quantitation of dibenzo[a,l]pyrene-DNA adducts formed by rat liver microsomes in vitro: preponderance of depurinating adducts. Biochemistry, 34, 8043-8049.
    • (1995) Biochemistry , vol.34 , pp. 8043-8049
    • Li, K.-M.1    Todorovic, R.2    Rogan, E.G.3    Cavalieri, E.L.4    Ariese, F.5    Suh, M.6    Jankowiak, R.7    Small, G.J.8
  • 8
    • 0020431144 scopus 로고
    • Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic compounds
    • Conney,A.H (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic compounds. Cancer Res., 42, 4875-491.
    • (1982) Cancer Res. , vol.42 , pp. 4875-5491
    • Conney, A.H.1
  • 9
    • 0028061909 scopus 로고
    • Synthesis and mutagenicity of the diastereomeric fjord-region 11,12-dihydrodiol 13,14-epoxides of dibenzo[a,l]pyrene
    • Luch,A., Glatt,H., Platt,K.L., Oesch,F. and Seidel,A. (1994) Synthesis and mutagenicity of the diastereomeric fjord-region 11,12-dihydrodiol 13,14-epoxides of dibenzo[a,l]pyrene. Carcinogenesis, 15, 2507-2516.
    • (1994) Carcinogenesis , vol.15 , pp. 2507-2516
    • Luch, A.1    Glatt, H.2    Platt, K.L.3    Oesch, F.4    Seidel, A.5
  • 10
    • 0027959934 scopus 로고
    • Synthesis and tumor-initiating activity in mouse skin of dibenzo[a,l]pyrene syn- and anti-fjord-region diolepoxides
    • Gill,H.S., Kole,P.L., Wiley,J C., Li,K.-M., Higginbotham,S., Rogan,E.G. and Cavalieri,E.L. (1994) Synthesis and tumor-initiating activity in mouse skin of dibenzo[a,l]pyrene syn- and anti-fjord-region diolepoxides. Carcinogenesis, 15, 2455-2460.
    • (1994) Carcinogenesis , vol.15 , pp. 2455-2460
    • Gill, H.S.1    Kole, P.L.2    Wiley, J.C.3    Li, K.-M.4    Higginbotham, S.5    Rogan, E.G.6    Cavalieri, E.L.7
  • 11
    • 0039799097 scopus 로고
    • Synthesis and structure determination of the adducts of dibenzo[a,l]pyrene diol epoxides and deoxyadenosine and deoxyguanosine
    • Li,K.-M., RamaKrisna,N.V.S , Padmavathi,N.S., Rogan,E G. and Cavalieri,E L. (1994) Synthesis and structure determination of the adducts of dibenzo[a,l]pyrene diol epoxides and deoxyadenosine and deoxyguanosine. Polycyclic Aromat. Comp., 6, 207-213
    • (1994) Polycyclic Aromat. Comp. , vol.6 , pp. 207-213
    • Li, K.-M.1    RamaKrisna, N.V.S.2    Padmavathi, N.S.3    Rogan, E.G.4    Cavalieri, E.L.5
  • 13
    • 15844426249 scopus 로고    scopus 로고
    • Relating aromatic hydrocarbon-induced DNA adducts and c-Harvey-ras mutations in mouse skin papillomas: The role of apurinic sites
    • in press
    • Chakravarti,D., Pelling,J.C , Cavalieri,E.L and Rogan,E.G. (1996) Relating aromatic hydrocarbon-induced DNA adducts and c-Harvey-ras mutations in mouse skin papillomas: the role of apurinic sites. Proc. Natl. Acad. Sci. USA. in press.
    • (1996) Proc. Natl. Acad. Sci. USA
    • Chakravarti, D.1    Pelling, J.C.2    Cavalieri, E.L.3    Rogan, E.G.4
  • 14
    • 0025777888 scopus 로고
    • Fluorescence line narrowing: A high-resolution window on DNA and protein damage from chemical carcinogens
    • Jankowiak,R. and Small,G.J. (1991) Fluorescence line narrowing: a high-resolution window on DNA and protein damage from chemical carcinogens. Chem. Res. Toxicol., 4, 256-269.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 256-269
    • Jankowiak, R.1    Small, G.J.2
  • 15
    • 0027207077 scopus 로고
    • Identification and quantitation of benzo[a]pyrene-DNA adducts formed in mouse skin
    • Rogan,E.G. et al. (1993) Identification and quantitation of benzo[a]pyrene-DNA adducts formed in mouse skin. Chem Res. Toxicol., 6, 356-363.
    • (1993) Chem Res. Toxicol. , vol.6 , pp. 356-363
    • Rogan, E.G.1
  • 17
    • 0028934966 scopus 로고
    • Identification of benzo[a]pyrene tetrols by reversed-phase liquid chromatography coupled semi-on-line to fluorescence line-narrowing spectroscopy
    • Kok,S.J., Posthumus,R., Bakker,I., Gooijer,C., Brinkman,U.A.Th. and Velthorst,N H. (1995) Identification of benzo[a]pyrene tetrols by reversed-phase liquid chromatography coupled semi-on-line to fluorescence line-narrowing spectroscopy. Anal. Chim. Acta. 303, 3-10.
    • (1995) Anal. Chim. Acta , vol.303 , pp. 3-10
    • Kok, S.J.1    Posthumus, R.2    Bakker, I.3    Gooijer, C.4    Brinkman, U.A.T.5    Velthorst, N.H.6
  • 18
    • 0028054816 scopus 로고
    • Sequence dependence of benzo[a]pyrene diol epoxide-DNA adduct conformer distribution: A study by laser-induced fluorescence/polyacrylamide gel electrophoresis
    • Marsch,G.A., Jankowiak,R., Suh,M. and Small,G.J. (1994) Sequence dependence of benzo[a]pyrene diol epoxide-DNA adduct conformer distribution: a study by laser-induced fluorescence/polyacrylamide gel electrophoresis. Chem. Res. Toxicol., 8, 98-109.
    • (1994) Chem. Res. Toxicol. , vol.8 , pp. 98-109
    • Marsch, G.A.1    Jankowiak, R.2    Suh, M.3    Small, G.J.4
  • 21
    • 84956382102 scopus 로고
    • DNA adducts formed by syn dihydodiol epoxides of polycyclic aromatic hydrocarbons
    • Szeliga,J., Hilton B.D., Lee,H., Harvey,R.G. and Dipple,A. (1994) DNA adducts formed by syn dihydodiol epoxides of polycyclic aromatic hydrocarbons. Polycyclic Aromat. Comp., 6, 87-93.
    • (1994) Polycyclic Aromat. Comp. , vol.6 , pp. 87-93
    • Szeliga, J.1    Hilton, B.D.2    Lee, H.3    Harvey, R.G.4    Dipple, A.5
  • 23
    • 0027466342 scopus 로고
    • Mutagenesis by the (+)-anti diol-epoxide of benzo[a]pyrene: What controls mutagenic specificity?
    • Rodriguez,H. and Loechler,E.L. (1993) Mutagenesis by the (+)-anti diol-epoxide of benzo[a]pyrene: what controls mutagenic specificity? Biochemistry, 32, 1759-1769.
    • (1993) Biochemistry , vol.32 , pp. 1759-1769
    • Rodriguez, H.1    Loechler, E.L.2
  • 24
    • 0027185882 scopus 로고
    • Translesional synthesis on a DNA template containing a single siereoisomer of dG-(+)- or dG-(-)-anti-BPDE (7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydro benzo[a]pyrene)
    • Shibutani,S., Margulis,L.A., Geacintov,N.E. and Grollman,A. (1993) Translesional synthesis on a DNA template containing a single siereoisomer of dG-(+)- or dG-(-)-anti-BPDE (7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydro benzo[a]pyrene). Biochemistry. 32, 7531-7541.
    • (1993) Biochemistry , vol.32 , pp. 7531-7541
    • Shibutani, S.1    Margulis, L.A.2    Geacintov, N.E.3    Grollman, A.4
  • 25
    • 0028800252 scopus 로고
    • Formation and persistence of benzo[a]pyrene-DNA adducts in mouse epidermis in vivo; importance of adduct conformation
    • Suh,M., Ariese,R. Small,G J., Jankowiak,R., Hewer,A. and Phillips,D.H. (1995) Formation and persistence of benzo[a]pyrene-DNA adducts in mouse epidermis in vivo; importance of adduct conformation. Carcinogenesis. 16, 2561-2569.
    • (1995) Carcinogenesis , vol.16 , pp. 2561-2569
    • Suh, M.1    Ariese, R.2    Small, G.J.3    Jankowiak, R.4    Hewer, A.5    Phillips, D.H.6
  • 28
    • 0012716939 scopus 로고
    • Triplet states via intermediate neglect of differential overlap: Benzene, pyridine, and the diazines Theoret
    • Ridley,J E. and Zerner,M.C. (1976) Triplet states via intermediate neglect of differential overlap: benzene, pyridine, and the diazines Theoret. Chim. Acta, 42, 223-236
    • (1976) Chim. Acta , vol.42 , pp. 223-236
    • Ridley, J.E.1    Zerner, M.C.2
  • 29
    • 36849107750 scopus 로고
    • Use of the CNDO method in spectroscopy I benzene, pyridine, and the diazines
    • Del Bene,J. and Jaffé,H.H. (1968) Use of the CNDO method in spectroscopy I benzene, pyridine, and the diazines. J. Chem. Phys., 48, 1807-1813.
    • (1968) J. Chem. Phys. , vol.48 , pp. 1807-1813
    • Del Bene, J.1    Jaffé, H.H.2
  • 30
    • 36849108774 scopus 로고
    • Use of the CNDO method in spectroscopy II. five-membered rings
    • Del Bene,J. and Jaffé,H.H. (1968) Use of the CNDO method in spectroscopy II. five-membered rings. J. Chem. Phys., 48, 4050-4055.
    • (1968) J. Chem. Phys. , vol.48 , pp. 4050-4055
    • Del Bene, J.1    Jaffé, H.H.2
  • 33
    • 0029007324 scopus 로고
    • Quantum mechanical studies of the structure and reactivities of the diol epoxides of benzo[c]phenanthrene
    • Lewis-Bevan,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
    • Lewis-Bevan, L.1    Little, S.B.2    Rabinowitz, J.R.3
  • 34
    • 15844414992 scopus 로고
    • Ph D. Thesis, University of Mainz, pp 127
    • Luch,A (1995) Ph D. Thesis, University of Mainz, pp 127.
    • (1995)
    • Luch, A.1
  • 36
    • 0023233999 scopus 로고
    • 7,12-Dimethylbenz[a]anthracene: Refined structure, electron density distribution and endo-peroxide structure
    • Klein,C.L., Stevens,E.D., Zacharias,D E. and Glusker,J.P. (1987) 7,12-Dimethylbenz[a]anthracene: refined structure, electron density distribution and endo-peroxide structure. Carcinogenesis, 8, 5-18.
    • (1987) Carcinogenesis , vol.8 , pp. 5-18
    • Klein, C.L.1    Stevens, E.D.2    Zacharias, D.E.3    Glusker, J.P.4
  • 37
    • 0024350051 scopus 로고
    • Steric strain and tumorigenicity: The molecular structure of 3,6-dimethylcholanthrene
    • Jones,D.W. and Shaw,J.D. (1989) Steric strain and tumorigenicity: the molecular structure of 3,6-dimethylcholanthrene. Carcinogenesis, 10, 1829-1831.
    • (1989) Carcinogenesis , vol.10 , pp. 1829-1831
    • Jones, D.W.1    Shaw, J.D.2
  • 38
    • 0041044362 scopus 로고
    • MO theoretical investigations of strained PAH molecules: Effects of methyl substituents in ground and excited states
    • Grimme,S. and Löhmannsroben,H.-G. (1992) MO theoretical investigations of strained PAH molecules: effects of methyl substituents in ground and excited states. J. Phys. Chem., 96, 7005-7009.
    • (1992) J. Phys. Chem. , vol.96 , pp. 7005-7009
    • Grimme, S.1    Löhmannsroben, H.-G.2
  • 39
    • 0020586368 scopus 로고
    • Enhancement of the skin tumor-initiating activity of polycyclic aromatic hydrocarbons by methyl-substitution at non-benzo 'bay-region' positions
    • DiGiovanni,J., Diamond,X., Harvey,R.G. and Slaga,T.I. (1983) Enhancement of the skin tumor-initiating activity of polycyclic aromatic hydrocarbons by methyl-substitution at non-benzo 'bay-region' positions. Carcinogenesis, 4, 403-407.
    • (1983) Carcinogenesis , vol.4 , pp. 403-407
    • DiGiovanni, J.1    Diamond, X.2    Harvey, R.G.3    Slaga, T.I.4
  • 40
    • 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, 327, 535-536.
    • (1987) Nature , 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
  • 41
    • 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. Interactions, 80, 177-186.
    • (1991) Chem.-Biol. Interactions , 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
  • 43
    • 0028940079 scopus 로고
    • Site-specific rates of excision repair of benzo[a]pyrene diol epoxide adducts in the hypoxanthine phosphoribosyl transferase gene of human fibroblasts: Correlation with mutation spectra
    • Wei,D., Maher, V. and McCormick,J.J. (1995) Site-specific rates of excision repair of benzo[a]pyrene diol epoxide adducts in the hypoxanthine phosphoribosyl transferase gene of human fibroblasts: correlation with mutation spectra. Proc. Natl. Acad. Sci. USA, 92, 2204-2208.
    • (1995) Proc. Natl. Acad. Sci. USA , vol.92 , pp. 2204-2208
    • Wei, D.1    Maher, V.2    McCormick, J.J.3


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