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Volumn 9, Issue 2, 1996, Pages 508-516

Detection of DNA and globin adducts of polynuclear aromatic hydrocarbon diol epoxides by gas chromatography - Mass spectrometry and [3H]CH3I postlabeling of released tetraols

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[A]PYRENE DERIVATIVE; CHRYSENE DERIVATIVE; DIHYDROXYBENZO[A]PYRENE OXIDE; GLOBIN; HEMOGLOBIN; POLYCYCLIC AROMATIC HYDROCARBON;

EID: 0029914480     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950165z     Document Type: Article
Times cited : (23)

References (44)
  • 5
    • 0019074870 scopus 로고
    • Benzo[α]pyrene metabolism, activation and carcinogenesis: Role and regulation of mixed functions
    • Gelboin, H. V (1980) Benzo[α]pyrene metabolism, activation and carcinogenesis: role and regulation of mixed functions. Physiol. Rev. 60, 1107-1166.
    • (1980) Physiol. Rev. , vol.60 , pp. 1107-1166
    • Gelboin, H.V.1
  • 6
    • 0020431144 scopus 로고
    • Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture
    • Conney, A. H. (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture. Cancer Res. 42, 4875-4917.
    • (1982) Cancer Res. , vol.42 , pp. 4875-4917
    • Conney, A.H.1
  • 7
    • 0028285404 scopus 로고
    • Polycyclic hydrocarbon activation: Bay regions and beyond
    • Phillips, D. H., and Grover, P. L. (1994) Polycyclic hydrocarbon activation: bay regions and beyond [review]. Drug Metab. Rev. 26, 443-467.
    • (1994) Drug Metab. Rev. , vol.26 , pp. 443-467
    • Phillips, D.H.1    Grover, P.L.2
  • 8
    • 0022267026 scopus 로고
    • Stereoselective metabolism and activations of polycyclic aromatic hydrocarbons
    • Yang, S. K., Mushtaq, M., and Chiu, P.-L. (1985) Stereoselective metabolism and activations of polycyclic aromatic hydrocarbons. J. Am. Chem. Soc. 107, 19-34.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 19-34
    • Yang, S.K.1    Mushtaq, M.2    Chiu, P.-L.3
  • 9
    • 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
  • 10
    • 26544445836 scopus 로고
    • Carcinogenicity of polycyclic aromatic hydrocarbons: The benzo-[α]pyrene-tetrols in blood protein adducts in rats after exposure to benzo[α]pyrene
    • Jerina, D. M., Sayer, J. M., Thakker, D. R., and Yagi, H. (1980) Carcinogenicity of polycyclic aromatic hydrocarbons: the benzo-[α]pyrene-tetrols in blood protein adducts in rats after exposure to benzo[α]pyrene. Anal. Chim. Acta 290, 85-93.
    • (1980) Anal. Chim. Acta , vol.290 , pp. 85-93
    • Jerina, D.M.1    Sayer, J.M.2    Thakker, D.R.3    Yagi, H.4
  • 11
    • 0019952179 scopus 로고
    • Stereoselective metabolism of the (-)- And (-)-enantiomers of trans-1,2-dihydroxy-1,2-dihydrochrysene to bay-region 1,2-diol-3,4-epoxide diastereomers by rat liver enzymes
    • Vyas, K. P., Levin, W., Yagi, H., Thakker, D. R., Ryan, D. E., Thomas, P. E., Conney, A. H., and Jerina, D. M. (1982) Stereoselective metabolism of the (-)- and (-)-enantiomers of trans-1,2-dihydroxy-1,2-dihydrochrysene to bay-region 1,2-diol-3,4-epoxide diastereomers by rat liver enzymes. Mol. Pharmacol. 22, 182-189.
    • (1982) Mol. Pharmacol. , vol.22 , pp. 182-189
    • Vyas, K.P.1    Levin, W.2    Yagi, H.3    Thakker, D.R.4    Ryan, D.E.5    Thomas, P.E.6    Conney, A.H.7    Jerina, D.M.8
  • 12
    • 0001361636 scopus 로고
    • Chemical characterization of DNA adducts derived from the configurationally isomeric benzo[c]phenanthrene-3,4-diol 1,2-epoxides
    • Agarwal, S. K., Sayer, J. M., Yeh, H. J., Pannell, L. K., Hilton, B. D., Pigott, M A., Dipple, A., Yagi, H., and Jerina, D. M. (1987) Chemical characterization of DNA adducts derived from the configurationally isomeric benzo[c]phenanthrene-3,4-diol 1,2-epoxides. J. Am. Chem. Soc. 109, 2497-2504.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2497-2504
    • Agarwal, S.K.1    Sayer, J.M.2    Yeh, H.J.3    Pannell, L.K.4    Hilton, B.D.5    Pigott, M.A.6    Dipple, A.7    Yagi, H.8    Jerina, D.M.9
  • 13
    • 0000481859 scopus 로고
    • Effect of bay region methyl group on reactions of anti benz[α]anthracene-3,4-dihydrodiol 1,2-epoxides with DNA
    • Peltonen, K., Cheng, S. C., Hilton, B. D., Lee, H., Cortez, C., Harvey, R. G., and Dipple, A. (1991) Effect of bay region methyl group on reactions of anti benz[α]anthracene-3,4-dihydrodiol 1,2-epoxides with DNA. J. Org. Chem. 56, 4181-4188.
    • (1991) J. Org. Chem. , vol.56 , pp. 4181-4188
    • Peltonen, K.1    Cheng, S.C.2    Hilton, B.D.3    Lee, H.4    Cortez, C.5    Harvey, R.G.6    Dipple, A.7
  • 14
    • 0024422388 scopus 로고
    • Formation of DNA hemoglobin adducts of fluoranthene after single and multiple exposures
    • Gorelick, N. J., Hutchins, D. A., Tannenbaum, R., and Wogan, G. N. (1989) Formation of DNA hemoglobin adducts of fluoranthene after single and multiple exposures. Carcinogenesis 10, 1579-1587.
    • (1989) Carcinogenesis , vol.10 , pp. 1579-1587
    • Gorelick, N.J.1    Hutchins, D.A.2    Tannenbaum, R.3    Wogan, G.N.4
  • 15
    • 0006905924 scopus 로고
    • Polycyclic aromatic hydrocarbon-DNA adducts and their analysis: A powerful technique for characterization of pathways of metabolic activation of hydrocarbons to ultimate carcinogenic metabolites
    • (Yang, S. K., and Silverman, B. D., Eds.) CRC Press, Boca Raton, FL
    • Baird, W. M., and Pruess-Schwartz, D. (1989) Polycyclic aromatic hydrocarbon-DNA adducts and their analysis: a powerful technique for characterization of pathways of metabolic activation of hydrocarbons to ultimate carcinogenic metabolites. In Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships (Yang, S. K., and Silverman, B. D., Eds.) pp 142-180, CRC Press, Boca Raton, FL.
    • (1989) Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships , pp. 142-180
    • Baird, W.M.1    Pruess-Schwartz, D.2
  • 16
    • 0000726357 scopus 로고
    • Methylchrysenes as probes for the mechanism of metabolic activation of carcinogenic methylated polynuclear aromatic hydrocarbons
    • Hecht, S. S., Melikian, A. A., and Amin, S. (1986) Methylchrysenes as probes for the mechanism of metabolic activation of carcinogenic methylated polynuclear aromatic hydrocarbons. Acc. Chem. Res. 19, 174-180.
    • (1986) Acc. Chem. Res. , vol.19 , pp. 174-180
    • Hecht, S.S.1    Melikian, A.A.2    Amin, S.3
  • 18
    • 0025763613 scopus 로고
    • 35S-phosphorothioate labeling and HPLC
    • 35S-phosphorothioate labeling and HPLC. Carcinogenesis 12, 885-893.
    • (1991) Carcinogenesis , vol.12 , pp. 885-893
    • Lau, H.H.S.1    Baird, W.M.2
  • 20
    • 0024493037 scopus 로고
    • Fluorescence and mass-spectral evidence for the formation of benzo[α]pyrene anti-diol epoxide-DNA and -hemoglobin adducts in humans
    • Weston, A., Rowe, M. L., Manchester, D. K., Farmer, P. B., Mann, D. L., and Harris, C. C. (1989) Fluorescence and mass-spectral evidence for the formation of benzo[α]pyrene anti-diol epoxide-DNA and -hemoglobin adducts in humans. Carcinogenesis 10, 251-257.
    • (1989) Carcinogenesis , vol.10 , pp. 251-257
    • Weston, A.1    Rowe, M.L.2    Manchester, D.K.3    Farmer, P.B.4    Mann, D.L.5    Harris, C.C.6
  • 21
    • 0025930778 scopus 로고
    • Benzo[α]pyrene-globin adducts detected by synchronous fluorescence spectrophotometry: Method development and relation to lung DNA adducts in mice
    • Bjelogrlic, N., and Vahakangas, K. (1991) Benzo[α]pyrene-globin adducts detected by synchronous fluorescence spectrophotometry: method development and relation to lung DNA adducts in mice. Carcinogenesis 12, 2205-2209.
    • (1991) Carcinogenesis , vol.12 , pp. 2205-2209
    • Bjelogrlic, N.1    Vahakangas, K.2
  • 22
    • 0039531870 scopus 로고
    • Fluoresence line-narrowing spectral analysis of in vivo human hemoglobin-benzo[α]pyrene adducts: Comparison to synthetic analogues
    • Jankowiak, R., Day, B. W., Lu, P.-Q., Doxtader, M. M., Skipper, P. L., Tannenbaum, S. R , and Small, G. J. (1990) Fluoresence line-narrowing spectral analysis of in vivo human hemoglobin-benzo[α]pyrene adducts: comparison to synthetic analogues. J. Am. Chem. Soc. 112, 5866-5869.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 5866-5869
    • Jankowiak, R.1    Day, B.W.2    Lu, P.-Q.3    Doxtader, M.M.4    Skipper, P.L.5    Tannenbaum, S.R.6    Small, G.J.7
  • 24
    • 0023011565 scopus 로고
    • Monoclonal antibodies to a benzo[α]pyrene diolepoxide modified protein
    • Santella, R. M., Lin, C. D., and Dharmaraja, N. (1986) Monoclonal antibodies to a benzo[α]pyrene diolepoxide modified protein. Carcinogenesis 7, 441-444.
    • (1986) Carcinogenesis , vol.7 , pp. 441-444
    • Santella, R.M.1    Lin, C.D.2    Dharmaraja, N.3
  • 26
    • 0027336992 scopus 로고
    • 2 chemical transformation/mass spectrometry detection of covalent damage to the DNA of cultured human lymphocytes exposed to benzo[α]-pyrene
    • 2 chemical transformation/mass spectrometry detection of covalent damage to the DNA of cultured human lymphocytes exposed to benzo[α]-pyrene Anal. Chem. 65, 1723-1731.
    • (1993) Anal. Chem. , vol.65 , pp. 1723-1731
    • Allam, K.1    Abdel-Baky, S.2    Giese, R.W.3
  • 27
    • 0028289755 scopus 로고
    • Benzo[α]pyrene diol epoxide and related polynuclear aromatic hydrocarbon adducts of hemoglobin
    • (Everse, J , Vandegriff, K. D., and Winslow, R. M., Eds.) Academic Press, San Diego, CA
    • Taghizadeh, K., and Skipper, P. L. (1994) Benzo[α]pyrene diol epoxide and related polynuclear aromatic hydrocarbon adducts of hemoglobin. In Hemoglobins Part B. Biochemical and Analytical Methods (Everse, J , Vandegriff, K. D., and Winslow, R. M., Eds.) pp 668-674, Academic Press, San Diego, CA.
    • (1994) Hemoglobins Part B. Biochemical and Analytical Methods , pp. 668-674
    • Taghizadeh, K.1    Skipper, P.L.2
  • 28
  • 29
    • 77955764774 scopus 로고
    • A rapid permethylation of glycolipid, and polysaccharide catalyzed by methylsulfinyl carbanion in dimethyl sulfoxide
    • Hakomori, S. (1964) A rapid permethylation of glycolipid, and polysaccharide catalyzed by methylsulfinyl carbanion in dimethyl sulfoxide. J. Biochem. 55, 205-208.
    • (1964) J. Biochem. , vol.55 , pp. 205-208
    • Hakomori, S.1
  • 30
    • 0037659922 scopus 로고
    • Complete sequence determination of proteins by mass spectrometry-rapid procedure for the successful permethylation of histidine containing peptides
    • Morris, H. R. (1972) Complete sequence determination of proteins by mass spectrometry-rapid procedure for the successful permethylation of histidine containing peptides. FEBS Lett. 22, 257-260.
    • (1972) FEBS Lett. , vol.22 , pp. 257-260
    • Morris, H.R.1
  • 31
    • 0020614875 scopus 로고
    • Carcinogenic metabolites of 5-methylchrysene
    • Pataki, J., Lee, H., and Harvey, R. G. (1983) Carcinogenic metabolites of 5-methylchrysene. Carcinogenesis 4, 399-402.
    • (1983) Carcinogenesis , vol.4 , pp. 399-402
    • Pataki, J.1    Lee, H.2    Harvey, R.G.3
  • 32
    • 0000294613 scopus 로고
    • An improved synthesis of anti-benzo[c]phenanthrene-3,4-diol-1,2-epoxide via 4-methoxybenzo-[c]phenanthrene
    • Misra, B., and Amin, S. (1990) An improved synthesis of anti-benzo[c]phenanthrene-3,4-diol-1,2-epoxide via 4-methoxybenzo-[c]phenanthrene. J. Org. Chem. 55, 4478-4480.
    • (1990) J. Org. Chem. , vol.55 , pp. 4478-4480
    • Misra, B.1    Amin, S.2
  • 33
    • 0023638181 scopus 로고
    • Enhancing effect of a bay region methyl group on tumorigenicity in newborn mice and mouse skin of enantiomeric bay region diol epoxides formed stereoselectively from methylchrysenes in mouse epidermis
    • Hecht, S. S., Amin, S., Huie, K., Melikian, A. A., and Harvey, R. G. (1987) Enhancing effect of a bay region methyl group on tumorigenicity in newborn mice and mouse skin of enantiomeric bay region diol epoxides formed stereoselectively from methylchrysenes in mouse epidermis. Cancer Res. 47, 5310-5315.
    • (1987) Cancer Res. , vol.47 , pp. 5310-5315
    • Hecht, S.S.1    Amin, S.2    Huie, K.3    Melikian, A.A.4    Harvey, R.G.5
  • 34
    • 0024325771 scopus 로고
    • Catechol-induced alterations in metabolic activation and binding of enantiomeric and racemic 7,8-dihydroxy-7,8-dihydrobenzo[α]-pyrenes to DNA in mouse skin
    • Melikian, A. A., Bagheri, K., Goldin, B. F., and Hoffmann, D. (1989) Catechol-induced alterations in metabolic activation and binding of enantiomeric and racemic 7,8-dihydroxy-7,8-dihydrobenzo[α]-pyrenes to DNA in mouse skin. Carcinogenesis 10, 1863-1870.
    • (1989) Carcinogenesis , vol.10 , pp. 1863-1870
    • Melikian, A.A.1    Bagheri, K.2    Goldin, B.F.3    Hoffmann, D.4
  • 35
    • 0021921601 scopus 로고
    • Quantitating exposure to chemical carcinogens: In vivo alkylation of hemoglobin by benzo[α]pyrene
    • Shugart, L. (1985) Quantitating exposure to chemical carcinogens: in vivo alkylation of hemoglobin by benzo[α]pyrene. Toxicology 34, 211-220.
    • (1985) Toxicology , vol.34 , pp. 211-220
    • Shugart, L.1
  • 36
    • 0020915088 scopus 로고
    • Quantifying benzo[α]pyrene binding to DNA by fluorescent analysis
    • (Cooke, M., and Dennis, A. J., Eds.) Battelle Press, Columbus, OH
    • Shugart, L., Rahn, R. O., and Holland, J. M. (1983) Quantifying benzo[α]pyrene binding to DNA by fluorescent analysis. In Polycyclic Aromatic Hydrocarbons: Formation, Metabolism and Measurement (Cooke, M., and Dennis, A. J., Eds.) pp 1087-1097, Battelle Press, Columbus, OH.
    • (1983) Polycyclic Aromatic Hydrocarbons: Formation, Metabolism and Measurement , pp. 1087-1097
    • Shugart, L.1    Rahn, R.O.2    Holland, J.M.3
  • 37
    • 0017779852 scopus 로고
    • Stereochemistry of the hydrolysis products and their acetonides of two stereoisomeric benzo[α]pyrene 7,8-diol-9,10-epoxides
    • Yang, S. K., McCourt, D. W., Gelboin, H. V., Miller, J. R., and Roller, P. P. (1977) Stereochemistry of the hydrolysis products and their acetonides of two stereoisomeric benzo[α]pyrene 7,8-diol-9,10-epoxides. J. Am. Chem. Soc. 99, 5124-5130.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 5124-5130
    • Yang, S.K.1    McCourt, D.W.2    Gelboin, H.V.3    Miller, J.R.4    Roller, P.P.5
  • 38
    • 0023821529 scopus 로고
    • Instability of (±)-7β,8α-hydroxy-9β,10β-epoxy-7,8,9,10- tetrahydrobenzo[α]pyrene (syn-BαPDE)-DNA adducts formed in benzo-[α]pyrene-treated Wistar rat embryo cell cultures
    • Pruess-Schwartz, D., Mauthe, R. J., and Baird, W. M. (1988) Instability of (±)-7β,8α-hydroxy-9β,10β-epoxy-7,8,9,10- tetrahydrobenzo[α]pyrene (syn-BαPDE)-DNA adducts formed in benzo-[α]pyrene-treated Wistar rat embryo cell cultures. Carcinogenesis 9, 1863-1868.
    • (1988) Carcinogenesis , vol.9 , pp. 1863-1868
    • Pruess-Schwartz, D.1    Mauthe, R.J.2    Baird, W.M.3
  • 39
    • 0028242053 scopus 로고
    • Liquid chromatographic analysis and stability of benzo[α]pyrene-tetrols in blood protein adducts in rats after exposure to benzo-[α]pyrene
    • Jansen, E. H. J. M., van den Berg, R. H., and Kroese, E. D. (1994) Liquid chromatographic analysis and stability of benzo[α]pyrene-tetrols in blood protein adducts in rats after exposure to benzo-[α]pyrene. Anal. Chim. Acta 290, 86-93.
    • (1994) Anal. Chim. Acta , vol.290 , pp. 86-93
    • Jansen, E.H.J.M.1    Van Den Berg, R.H.2    Kroese, E.D.3
  • 40
    • 0024442239 scopus 로고
    • DNA adducts from carcinogenic and noncarcinogenic enantiomers of benzo[α]pyrene dihydrodiol epoxide
    • Cheng, S. C., Hilton, B. D , Roman, J. M., and Dipple, A. (1989) DNA adducts from carcinogenic and noncarcinogenic enantiomers of benzo[α]pyrene dihydrodiol epoxide. Chem. Res. Toxicol. 2, 334-340.
    • (1989) Chem. Res. Toxicol. , vol.2 , pp. 334-340
    • Cheng, S.C.1    Hilton, B.D.2    Roman, J.M.3    Dipple, A.4
  • 41
    • 0019777522 scopus 로고
    • Inhibition in vivo of the formation of adducts between metabolites of benzo[α]pyrene and DNA by butylated hydroxyanisole
    • Anderson, M. W., Boroujerdi, M., and Wilson, A. G. E. (1981) Inhibition in vivo of the formation of adducts between metabolites of benzo[α]pyrene and DNA by butylated hydroxyanisole. Cancer Res. 41, 4309-4315.
    • (1981) Cancer Res. , vol.41 , pp. 4309-4315
    • Anderson, M.W.1    Boroujerdi, M.2    Wilson, A.G.E.3
  • 42
    • 0021171757 scopus 로고
    • Ubiquitous binding of benzo[α]pyrene metabolites to DNA and protein in tissues of the mouse and rabbit
    • Stowers, S. J., and Anderson, M. W. (1984) Ubiquitous binding of benzo[α]pyrene metabolites to DNA and protein in tissues of the mouse and rabbit Chem.-Biol. Interact. 51, 151-166.
    • (1984) Chem.-Biol. Interact. , vol.51 , pp. 151-166
    • Stowers, S.J.1    Anderson, M.W.2
  • 43
    • 0025195668 scopus 로고
    • Molecular dosimetry of polycyclic aromatic hydrocarbon epoxides and diol epoxides via hemoglobin adducts
    • Day, B. W., Naylor, S., Gan, L. S., Sahali, Y., Nguyen, T. T., Skipper, P. L., Wishnok, J. S., and Tannenbaum, S. R. (1990) Molecular dosimetry of polycyclic aromatic hydrocarbon epoxides and diol epoxides via hemoglobin adducts. Cancer Res. 50, 4611-4618.
    • (1990) Cancer Res. , vol.50 , pp. 4611-4618
    • Day, B.W.1    Naylor, S.2    Gan, L.S.3    Sahali, Y.4    Nguyen, T.T.5    Skipper, P.L.6    Wishnok, J.S.7    Tannenbaum, S.R.8


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