Skip to main content
SpringerLink
Log in
Book cover

Biological Reactive Intermediates IV pp 533–553Cite as

Covalent Bonding of Bay-Region Diol Epoxides to Nucleic Acids

  • Chapter

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 283))

Abstract

Fifteen years ago, we proposed bay-region diol epoxides as the reactive metabolites responsible for the tumorigenic activity of polycyclic aromatic hydrocarbons (Jerina and Daly, 1976; Jerina et al., 1976; Jerina and Lehr, 1977). In the intervening period, extensive studies from several laboratories have provided substantial evidence that over a dozen hydrocarbons are activated by this pathway (Jerina et al., 1984; Lehr et al., 1985; Thakker et al., 1985). Examples have been forthcoming from a variety of structural types including benz- and dibenzanthracenes and acridines, benz- and dibenzpyrenes, chrysenes, and benzo[c]phenanthrene. To date, there are no known examples of carcinogenic alternant polycyclic aromatic hydrocarbons for which a bay-region diol epoxide is not an ultimate carcinogen. Although a number of mechanistically attractive alternatives to bay-region diol epoxides exist (Watabe et al., 1989; Cavalieri and Rogan, 1985; Miller et al., this volume), the extent of their contribution to the overall carcinogenicity of the hydrocarbons remains to be established.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Abrams, W. R. and Kallen, R. G. (1976). Estimates of microscopic ionization constants for heteroaromatic exocyclic amines including purine and pyrimidine nucleotides and amides based upon a reactivity-basicity correlation for N-hydroxymethylation reactions with formaldehyde. J. Am. Chem. Soc. 98, 7789–7792.

    Article  CAS  Google Scholar 

  • Anderson, M. W., You, M., Maronpot, R. R. and Reynolds, S. (1991). Proto-oncogene activation in rodent and human tumors. This volume.

    Google Scholar 

  • Agarwal, S. K., Sayer, J. M., Yeh, H. J. C., 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.

    Article  CAS  Google Scholar 

  • Bigger, C. A. H., Strandberg, J., Yagi, H., Jerina, D. M. and Dipple, A. (1989). Mutagenic specificity of a potent carcinogen, benzo[c]phenanthrene (4R,3S)-diol (2S,1R)-epoxide, which reacts with adenine and guanine in DNA. Proc. Natl. Acad. Sci USA. 86, 2291–2295.

    Article  CAS  PubMed  Google Scholar 

  • Bizub, D., Wood, A. W. and Skalka, A. M. (1986). Mutagenesis of the Ha-ras oncogene in mouse skin tumors induced by polycyclic aromatic hydrocarbons. Proc. Natl. Acad. Sci. USA 83, 6048–6052.

    Article  CAS  PubMed  Google Scholar 

  • Boles, T. C. and Hogan, M. E. (1986). High-resolution maping of carcinogen binding sites on DNA. Biochemistry 25, 3039–3043.

    Article  CAS  PubMed  Google Scholar 

  • Bowden, G. T. (1991). Oncogene activation and differential gene expression during multistage skin carcinogenesis. This volume.

    Google Scholar 

  • Carberry, S. E., Shahbaz, M., Geacintov, N. E. and Harvey, R. G. (1988). Reactions of stereoisomeric and structurally related bay region diol epoxide derivatives of benz[a]anthracene with DNA. Conformations of non-covalent complexes and covalent carcinogen-DNA adducts. Chem.-Biol. Interactions 66, 121–145.

    Article  CAS  Google Scholar 

  • Carberry, S. E., Geacintov, N. E. and Harvey, R. G. (1989). Reactions of stereoisomeric non-bay-region benz[a]anthracene diol epoxides with DNA and conformations of non-covalent complexes and covalent adducts. Carcinogenesis 10, 97–103.

    Article  CAS  PubMed  Google Scholar 

  • Carothers, A. M. and Grunberger, D. (1990). DNA base changes in benzo[a]pyrene diol epoxide-induced dihydrofolate reductase mutants of Chinese hamster ovary cells. Carcinogenesis 11, 189–192.

    Article  CAS  PubMed  Google Scholar 

  • Cavalieri, E. L. and Rogan, E. G. (1985). One-electron oxidation in aromatic hydrocarbon carcinogenesis. In Polycyclic Hydrocarbons and Carcinogenesis (ACS Symposium Series No. 283) ( R. G. Harvey, Ed.), pp. 289–305. American Chemical Society, Washington, DC.

    Chapter  Google Scholar 

  • Chadha, A., Sayer, J. M., Yeh, H. J. C., Yagi, H., Cheh, A. M., Pannell, L. K. and Jerina, D. M. (1989). Structures of covalent nucleoside adducts formed from adenine, guanine and cytosine bases of DNA and the optically active bay-region 3,4-diol 1,2-epoxides derived from dibenz[a,j]anthracene. J. Am. Chem. Soc. 111, 5456–5463.

    Article  CAS  Google Scholar 

  • Chadha, A., Sayer, J. M., Agarwal, S, K., Cheh, A. M., Yagi, H., Yeh, H. J. C. and Jerina, D. M. (1990). Formation of covalent adducts between DNA and optically active bay-region diol epoxides of dibenz[a,j]anthracene. In Polynuclear Aromatic Hydrocarbons: Measurements, Means and Metabolism ( M. Cooke, K. Loening, and J. Merritt, Eds.), pp. 179–194. Battelle Press, Columbus, OH.

    Google Scholar 

  • 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. Nati. Acad. Sci. USA 84, 8633–8636.

    Article  CAS  Google Scholar 

  • Cheng, S. C., Prakash, A. S., Pigott, M. A., Hilton, B. D., Roman, J. M., Lee, H., Harvey, R. G. and Dipple, A. (1988a). Characterization of 7,12- dimethylbenz[a]anthracene-adenine nucleoside adducts. Chem. Res. Toxicol. 1, 216–221.

    Article  CAS  PubMed  Google Scholar 

  • Cheng, S. C., Prakash, A. S., Pigott, M. A., Hilton, B. D., Lee, H., Harvey, R. G., and Dipple, A. (1988b). A metabolite of the carcinogen 7,12- dimethylbenz[a]anthracene that reacts predominantly with adenine residues in DNA. Carcinogenesis 9, 1721–1723.

    Article  CAS  PubMed  Google Scholar 

  • Cheng, S. C., Hilton, B. D., Roman, J. M., and Dipple, A. (1989). DNA adducts from carcinogenic and noncarcinogenic enantiomers of benzo[a]pyrene dihydrodiol epoxide. Chem. Res. Toxicol. 2, 334–340.

    Article  CAS  PubMed  Google Scholar 

  • 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.

    Article  CAS  PubMed  Google Scholar 

  • Eisenstadt, E., Warren, A. J., Porter, J., Atkins, D. and Miller, J. H. (1982). Carcinogenic epoxides of benzo[a]pyrene and cyclopenta[c,d]pyrene induce base substitutions via specific transversions. Proc. Natl. Acad. Sci. USA 79, 1945–1949.

    Article  CAS  Google Scholar 

  • Eriksson, M., Nordén, B., Jernstrdm, B. and Gräslund, A. (1988). Binding geometries of benzo[a]pyrene diol epoxide isomers covalently bound to DNA. Orientational distribution. Biochemistry 27, 1213–1221.

    Article  CAS  PubMed  Google Scholar 

  • Gagliano, A. G., Geacintov, N. E., Ibanez, V., Harvey, R. G. and Lee, H. M. (1982). Application of fluorescence and linear dichroism techniques to the characterization of the covalent adducts derived from interaction of (±)-trans-9,10-dihydroxy-anti-11,12-epoxy-9,10,11,12-tetrahydro-benzo[e]pyrene with DNA. Carcinogenesis 3, 969–976.

    Article  CAS  PubMed  Google Scholar 

  • Geacintov, N. E. (1985). Mechanisms of interaction of polycyclic aromatic diol epoxides with DNA and structures of the adducts. In Polycyclic Hydrocarbons and Carcinogenesis (ACS Symposium Series No. 283) ( R. G. Harvey, Ed.), pp. 107–124. American Chemical Society, Washington, DC.

    Chapter  Google Scholar 

  • Geacintov, N. E. (1986). Is intercalation a critical factor in the covalent binding of mutagenic and tumorigenic polycyclic aromatic diol epoxides to DNA? Carcinogenesis 7, 759–766.

    Article  CAS  PubMed  Google Scholar 

  • Geacintov, N. E. (1988). Mechanisms of reaction of polycyclic aromatic epoxide derivatives with nucleic acids. In Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships, Volume II ( S. K. Yang and B. D. Silverman, Eds.), pp. 181–206. CRC Press, Boca Raton, FL.

    Google Scholar 

  • Geacintov, N. E., Yoshida, H., Ibanez, V. and Harvey, R. G. (1981). Non-covalent intercalative binding of 7,8-dihydroxy-9,10-epoxy-benzo[alpyrene to DNA. Biochem. Biophys. Res. Commun. 100, 1569–1577.

    Article  CAS  PubMed  Google Scholar 

  • Geacintov, N. E., Gagliano, A. G., Ibanez, V. and Harvey, R. G. (1982a). Spectroscopic characterizations and comparisons of the structures of the covalent adducts derived from the reactions of 7,8-dihydroxy-7,8,9,10- tetrahydrobenzo[alpyrene-9,10-oxide, and the 9,10-epoxides of 7,8,9,10-tetrahydrobenzo[a]pyrene and 9,10,11,12-tetrahydrobenzo[e]pyrene with DNA. Carcinogenesis 3, 247–253.

    Article  CAS  PubMed  Google Scholar 

  • Geacintov, N. E., Yoshida, H., Ibanez, V. and Harvey, R. G. (1982b). Noncovalent binding of 713,8a-dihydroxy-9a,10a-epoxytetrahydrobenzo[a]pyrene to deoxyribonucleic acid and its catalytic effect on the hydrolysis of the diol epoxide to tetrol. Biochemistry 21, 1864–1869.

    Article  CAS  PubMed  Google Scholar 

  • Geacintov, N. E., Hibshoosh, H., Ibanez, V., Benjamin, M. J. and Harvey, R. G. (1984). Mechanisms of reaction of benzo[a]pyrene-7,8-dio1–9,10-epoxide with DNA in aqueous solutions. Biophysical Chemistry 20, 121–133.

    Article  CAS  PubMed  Google Scholar 

  • Geacintov, N. E., Shahbaz, M., Ibanez, V., Moussaoui, K., and Harvey, R. G. (1988). Base-sequence dependence of noncovalent complex formation and reactivity of benzo[a]pyrene diol epoxide with polynucleotides. Biochemistry 27, 8380–8387.

    Article  CAS  PubMed  Google Scholar 

  • Grtislund, A. and Jernström, B. (1989). DNA-carcinogen interaction: covalent DNA-adducts of benzo[a]pyrene 7,8-dihydrodiol 9,10-epoxides studied by biochemical and biophysical techniques. Quart. Rev. Biophys. 22, 1–37.

    Google Scholar 

  • Gupta, S. C., Islam, N. B., Whalen, D. L., Yagi, H. and Jerina, D. M. (1987). Bifunctional catalysis in the nucleotide-catalyzed hydrolysis of (±)-713,8a-dihydroxy-9a,10a-epoxy-7,8,9,10-tetrahydrobenzoajpyrene. J. Org. Chem. 52, 3812–3815.

    Article  CAS  Google Scholar 

  • Hogan, M. E., Dattagupta, N. and Whitlock, J. P., Jr. (1981). Carcinogen-induced alteration of DNA structure. J. Biol. Chem. 256, 4504–4513.

    CAS  PubMed  Google Scholar 

  • Islam, N. B., Whalen, D. L., Yagi, H. and Jerina, D. M. (1987). pH Dependence of the mechanism of hydrolysis of benzo[a]pyrene-cis-7,8-diol 9,10-epoxide catalyzed by DNA, poly(G), and poly(A). J. Am. Chem. Soc. 109, 2108–2111.

    Google Scholar 

  • Islam, N. B., Whalen, D. L., Yagi, H. and Jerina, D. M. (1990). Differences in the mechanisms of the spontaneous hydrolysis reactions of bay region benzo[a]pyrene 7,8-diol 9,10-epoxides: Trapping of a carbocationic intermediate. J. Am. Chem. Soc. 112 in press.

    Google Scholar 

  • Jerina, D. M. and Daly, J. W. (1976). Oxidation at Carbon. In Drug Metabolism-from Microbe to Man ( D. V. Parke and R. L. Smith, Eds.), pp. 13–32. Taylor and Francis Ltd., London, UK.

    Google Scholar 

  • Jerina, D. M., Lehr, R. E., Yagi, H., Hernandez, O., Dansette, P. M., Wislocki, P. G., Wood, A. W., Chang, R. L., Levin, W. and Conney, A. H. (1976). Mutagenicity of benzo[a]pyrene derivatives and the description of a quantum mechanical model which predicts the ease of carbonium ion formation from diol epoxides. In In Vitro Metabolic Activation In Mutagenesis Testing ( F. J. de Serres, J. R. Fouts, J. R. Bend, and R. M. Philpot, Eds.), pp. 159–177. Elsevier/North-Holland Biomedical Press, Amsterdam.

    Google Scholar 

  • Jerina, D. M. and Lehr, R. E. (1977). The bay-region theory: A quantum mechanical approach to aromatic hydrocarbon-induced carcinogenicity. In Microsomes and Drug Oxidations (Proceedings of the 3rd International Symposium) ( V. Ullrich, I. Roots, A. G. Hildebrandt, R. W. Estabrook, and A. H. Conney, Eds.), pp. 709–720. Pergamon Press, Oxford, UK.

    Google Scholar 

  • Jerina, D. M., Yagi, H., Thakker, D. R., Sayer, J. M., van Bladeren, P. J., Lehr, R. E., Whalen, D. L., Levin, W., Chang, R. L., Wood, A. W. and Conney, A. H. (1984). Identification of the ultimate carcinogenic metabolites of the polycyclic aromatic hydrocarbons: Bay-region (R,S)-diol-(S,R)-epoxides. In Foreign Compound Metabolism ( J. Caldwell and G. D. Paulson, Eds.), pp. 257–266. Taylor and Francis Ltd., London, UK.

    Google Scholar 

  • Jerina, D. M., Sayer, J. M., Yagi, H., van Bladeren, P. J., Thakker, D. R., Levin, W., Chang, R. L., Wood, A. W. and Conney, A. H. (1985). Stereoselective metabolism of polycyclic aromatic hydrocarbons to carcinogenic metabolites. In Microsomes and Drug Oxidations ( A. R. Boobis, J. Caldwell, F. De Matteis, and C. R. Elcombe, Eds.), pp. 310–319. Taylor and Francis Ltd., London, UK.

    Google Scholar 

  • Jerina, D. M., Sayer, J. M., Agarwal, S. K., Yagi, H., Levin, W., Wood, A. W., Conney, A. H., Pruess-Schwartz, D., Baird, W. M., Pigott, M. A. and Dipple, A. (1986). Reactivity and tumorigenicity of bay-region diol epoxides derived from polycyclic aromatic hydrocarbons. In Biological Reactive Intermediates III. ( J. J. Kocsis, D. J. Jollow, C. M. Witmer, J. O. Nelson, and R. Snyder, Eds.), pp. 11–30. Plenum Press, New York.

    Chapter  Google Scholar 

  • Jerina, D. M., Cheh, A. M., Chadha, A., Yagi, H. and Sayer, J. M. (1988). Binding of metabolically formed bay-region diol epoxides to DNA. In Microsomes and Drug Oxidations: Proceedings of the 7th International Symposium ( J. O. Miners, D. J. Birkett, R. Drew, B. K. May, and M. E. McManus, Eds.), pp. 354–362. Taylor and Francis, London, UK.

    Google Scholar 

  • Jernstrtim, B., Lycksell, P.-O., Gräslund, A. and Nordén, B. (1984). Spectroscopic studies of DNA complexes formed after reaction with anti-benzo[a]pyrene-7,8dihydrodiol-9,10-oxide enantiomers of different carcinogenic potency. Carcinogenesis 5, 1129–1135.

    Article  Google Scholar 

  • Kasai, H., Nakanishi, K. and Traiman, S. (1978). Two micromethods for determining the linkage of adducts formed between polyaromatic hydrocarbons and nucleic acid bases. J. Chem. Soc. Chem. Commun. 1, 798–800.

    Article  Google Scholar 

  • Kim, M.-H., Geacintov, N. E., Pope, M. and Harvey, R. G. (1984). Structural effects in reactivity and adduct formation of polycyclic aromatic epoxide and diol epoxide derivatives with DNA: Comparisons between 1-oxiranylpyrene and benzo[a]pyrenediol epoxide. Biochemistry 23, 5433–5439.

    Article  CAS  PubMed  Google Scholar 

  • Kim, M.-H., Geacintov, N. E., Pope, M., Pataki, J. and Harvey, R. G. (1985). Reaction mechanisms of trans-1,2-dihydroxy-anti-3,4-epoxy-1,2,3,4-tetrahydro-5methylchrysene with DNA in aqueous solutions. Carcinogenesis 6, 121–126.

    Article  CAS  PubMed  Google Scholar 

  • Kim, M.-H., Geacintov, N. E., McQuillen, D. G., Pope, M., and Harvey, R. G. (1986). Reaction mechanisms of trans-1,2-dihydroxy-anti-7,8-epoxy-7,8,9,10tetrahydro-3-methylcholanthrene with DNA in aqueous solutions. Conformation of adducts. Carcinogenesis 7, 41–47.

    Article  CAS  PubMed  Google Scholar 

  • Koostra, A., Lew, L. K., Nairn, R. S. and MacLeod, M.C. (1989). Preferential modification of GC boxes by benzo[a]pyrene-7,8-dio1–9,10-epoxide. Mol. Carcinogenesis 1, 239–244.

    Article  Google Scholar 

  • Lehr, R. E., Kumar, S., Levin, W., Wood, A. W., Chang, R. L., Conney, A. H., Yagi, H., Sayer, J. M. and Jerina, D. M. (1985). The bay-region theory of polycyclic aromatic hydrocarbon carcinogenesis. In Polycyclic Hydrocarbons and Carcinogenesis (ACS Symposium Series No. 283) ( R. G. Harvey, Ed.), pp. 63–84. American Chemical Society, Washington, DC.

    Google Scholar 

  • 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.

    CAS  Google Scholar 

  • MacLeod, M. C. (1990). The importance of intercalation in the covalent binding of benzo[a]pyrene diol epoxide to DNA. J. Theor. Biol. 142, 113–132.

    CAS  Google Scholar 

  • MacLeod, M. C. and Zachary, K. L. (1985a). Involvement of the exocyclic amino group of deoxyguanosine in DNA-catalysed carcinogen detoxification. Carcinogenesis 6, 147–149.

    Article  CAS  PubMed  Google Scholar 

  • MacLeod, M. C. and Zachary, K. (1985b). Catalysis of carcinogen-detoxification by DNA: comparison of enantiomeric diol epoxides. Chem.-Biol. Interactions 54, 45–55.

    Article  CAS  Google Scholar 

  • Meehan, T. and Bond, D. M. (1984). Hydrolysis of benzo[a]pyrene diol epoxide and its covalent binding to DNA proceed through similar rate-determining steps. Proc. Natl. Acad. Sci. USA 81, 2635–2639.

    Article  CAS  Google Scholar 

  • Michaud, D. P., Gupta, S. C., Whalen, D. L., Sayer, J. M. and Jerina, D. M. (1983). Effects of pH and salt concentration on the hydrolysis of a benzo[a]pyrene 7,8- dio1–9,10-epoxide catalyzed by DNA and polyadenylic acid. Chem.-Biol. Interactions 44, 41–52.

    Article  CAS  Google Scholar 

  • Miller, J. A., Surh, Y.-J. and Miller, E. C. (1991). Electrophylic sulfuric acid ester metabolites of hydroxymethyl aromatic hydrocarbons as precursors of hepatic benzylic DNA adducts in vivo. This volume.

    Google Scholar 

  • Moore, P. D., Koreeda, M., Wislocki, P. G., Levin, W., Conney, A. H., Yagi, H. and Jerina, D. M. (1977). In vitro reactions of the diastereomeric 9,10-epoxides of (+)- and (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene with polyguanylic acid and evidence for formation of an enantiomer of each diastereomeric 9,10- epoxide from benzo[a]pyrene in mouse skin. In Drug Metabolism Concepts (ACS Symposium Series No. 44) (D. M. Jerina, Ed.), pp. 127–154. American Chemical Society, Washington, DC.

    Google Scholar 

  • Reardon, D.B., Prakash, A. S., Hilton, B. D., Roman, J. M., Pataki, J., Harvey, R. G. and Dipple, A. (1987). Characterization of 5-methylchrysene-1,2-dihydrodiol-3,4-epoxide-DNA adducts. Carcinogenesis 8, 1317–1322.

    Article  CAS  PubMed  Google Scholar 

  • Reardon, D. B., Bigger, C. A., Strandberg, J., Yagi, H., Jerina, D. M. and Dipple, A. (1989). Sequence selectivity in the reaction of optically active hydrocarbon dihydrodiol epoxides with H-ras DNA. Chem. Res. Toxicol. 2, 12–14.

    Article  CAS  PubMed  Google Scholar 

  • Reardon, D. B,. Bigger, C. A. and Dipple, A. (1990). DNA polymerase action on bulky deoxyguanosine and deoxyadenosine adducts. Chem. Res. Toxicol. 3, 165–168.

    Google Scholar 

  • Roche, C. J., Geacintov, N. E., Ibanez, V., and Harvey, R. G. (1989). Linear dichroism properties and orientations of different ultraviolet transition moments of benzo[a]pyrene derivatives bound noncovalently and covalently to DNA. Biophysical Chemistry 33, 277–288.

    Article  CAS  PubMed  Google Scholar 

  • Sayer, J. M., Yagi, H., Croisy-Delcey, M. and Jerina, D. M. (1981) Novel bay-region diol epoxides from benzo[c]phenanthrene. J. Am. Chem. Soc. 103, 4970–4972.

    Article  CAS  Google Scholar 

  • Sayer, J. M., Lehr, R. E., Whalen, D. L., Yagi, H. and Jerina, D. M. (1982a). Structure-reactivity indices for the hydrolysis of diol epoxides of polycyclic aromatic hydrocarbons. Tetrahedron Lett. 23, 4431–4434.

    Article  CAS  Google Scholar 

  • Sayer, J. M., Yagi, H., Wood, A. W., Conney, A. H. and Jerina, D. M. (1982b). Extremely facile reaction between the ultimate carcinogen benzo[a]pyrene-7,8- diol 9,10-epoxide and ellagic acid. J. Am. Chem. Soc. 104, 5562–5564.

    Article  CAS  Google Scholar 

  • Sayer, J. M., Chadha, A., Agarwal, S. K., Yeh, H. J. C., Yagi, H., and Jerina, D. M. (1990). Covalent nucleoside adducts of benzo[a]pyrene 7,8-diol 9,10- epoxides: Structural reinvestigation and characterization of a novel adenosine adduct on the ribose moiety. J. Org. Chem. 55, in press.

    Google Scholar 

  • Strauss, B., Turkington, E., Sahm, J. and Wang, J. (1991). Mutagenic consequences of the alteration of DNA by chemicals and radiation. This volume.

    Google Scholar 

  • Schurdak M. E., Bekesi, E., Jerina, D. M., Yagi, H., Bushman, D. R., Lehr, R. E. and Wood, A. W. (1990). Proc. Am. Assoc. Cancer Res. 31, 90.

    Google Scholar 

  • 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 (M. W. Anders, Ed.), pp. 177–242. Academic Press, New York.

    Google Scholar 

  • 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.

    Article  CAS  PubMed  Google Scholar 

  • Watabe, T., Ogura, K., Okuda, H., and Hiratsuka, A. (1989). Hydroxymethyl sulfate esters as reactive metabolites of the carcinogens 7-methyl-and 7,12- dimethylbenz[a]anthracenes and 5-methylchrysene. In Xenobiotic Metabolism and Disposition ( R. Kato, R. W. Estabrook, and M. N. Cayen, Eds.), pp. 393–400. Taylor and Francis, London, UK.

    Google Scholar 

  • Whalen, D. L., Montemarano, J. A., Thakker, D. R., Yagi, H. and Jerina, D. M. (1977). Changes of mechanism and product distributions in the hydrolysis of benzo[a]pyrene 7,8-diol 9,10-epoxide metabolites induced by changes in pH. J. Am. Chem. Soc. 99, 5522–5524.

    Article  CAS  PubMed  Google Scholar 

  • Whalen, D. L., Ross, A. M., Yagi, H., Karle, J. M. and Jerina, D. M. (1978). Stereoelectronic factors in the solvolysis of bay region diol epoxides of polycyclic aromatic hydrocarbons. J. Am. Chem. Soc. 100, 5218–5221.

    Article  CAS  Google Scholar 

  • Whalen, D. L., Ross, A. M., Montemarano, J. A., Thakker, D. R., Yagi, H. and Jerina, D. M. (1979). General acid catalysis in the hydrolysis of benzo[a]pyrene 7,8-diol 9,10-epoxides. J. Am. Chem. Soc. 101, 5086–5088.

    Article  CAS  Google Scholar 

  • Whalen, D. L., Islam, N. B., Gupta, S. C., Sayer, J. M. and Jerina, D. M. (1990). Kinetic studies of the reactions of benzo[a]pyrene 7,8-diol 9,10-epoxides with general acids, nucleotides, DNA and micelles. In Polynuclear Aromatic Hydrocarbons: Measurements, Means and Metabolism ( M. Cooke, K. Loening and J. Merritt, Eds.), pp. 1017–1032. Battelle Press, Columbus, OH.

    Google Scholar 

  • Wood, A. W., Sayer, J. M., Newmark, H. L., Yagi, H., Michaud, D. P., Jerina, D. M. and Conney, A. H. (1982). Mechanism of the inhibition of mutagenicity of a benzo[a]pyrene 7,8-diol 9,10-epoxide by riboflavin 5’-phosphate. Proc. Natl. Acad. Sci. USA 79, 5122–5126.

    Article  CAS  Google Scholar 

  • Yagi, H., Thakker, D. R., Hernandez, O., Koreeda, M. and Jerina, D. M. (1977). Synthesis and reactions of the highly mutagenic 7,8-diol 9,10-epoxides of the carcinogen benzo[a]pyrene. J. Am. Chem. Soc. 99, 1604–1611.

    Article  CAS  PubMed  Google Scholar 

  • Yagi, H., Sayer, J. M., Thakker, D. R., Levin, W. and Jerina, D. M. (1987). Effects of a 6-fluoro substituent on the solvolytic properties of the diastereomeric 7,8-diol 9,10-epoxides of the carcinogen benzo[a]pyrene. J. Am. Chem. Soc. 109, 838–846.

    Article  CAS  Google Scholar 

  • Yang, J.-L., Maher, V. M. and McCormick, J. J. (1987). Kinds of mutations formed when a shuttle vector containing adducts of (±)-7ß,8a-dihydroxy-9a,10a-epoxy7,8,9,10-tetrahydrobenzo[a]pyrene replicates in human cells. Proc. Nati. Acad. Sci. USA 84, 3787–3791.

    Article  CAS  Google Scholar 

  • You, M., Candrian, U., Maronpot, R. R., Stoner, G. D. and Anderson, M. W. (1989). Activation of the Ki-ras protooncogene in spontaneously occurring and chemically induced lung tumors of the strain A mouse. Proc. Natl. Acad. Sci. USA 86, 3070–3074.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratory of Bioorganic Chemistry, The National Institutes of Health NIDDK, Bethesda, MD, 20892, USA

    Donald M. Jerina, Anju Chadha, Albert M. Cheh & Jane M. Sayer

  2. Department of Oncology, The National Institutes of Health NIDDK, Bethesda, MD, 20892, USA

    Mark E. Schurdak & Alexander W. Wood

  3. Roche Research Center, Nutley, NJ, 07110, USA

    Donald M. Jerina, Anju Chadha, Albert M. Cheh, Mark E. Schurdak, Alexander W. Wood & Jane M. Sayer

Authors
  1. Donald M. Jerina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anju Chadha
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Albert M. Cheh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mark E. Schurdak
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Alexander W. Wood
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jane M. Sayer
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Rutgers University, Piscataway, New Jersey, USA

    Charlotte M. Witmer  & Robert R. Snyder  & 

  2. Medical University of South Carolina, Charleston, South Carolina, USA

    David J. Jollow

  3. Thomas Jefferson University, Philadelphia, Pennsylvania, USA

    George F. Kalf  & James J. Kocsis  & 

  4. University of Arizona, Tucson, Arizona, USA

    I. Glenn Sipes

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Plenum Press, New York

About this chapter

Cite this chapter

Jerina, D.M., Chadha, A., Cheh, A.M., Schurdak, M.E., Wood, A.W., Sayer, J.M. (1991). Covalent Bonding of Bay-Region Diol Epoxides to Nucleic Acids. In: Witmer, C.M., Snyder, R.R., Jollow, D.J., Kalf, G.F., Kocsis, J.J., Sipes, I.G. (eds) Biological Reactive Intermediates IV. Advances in Experimental Medicine and Biology, vol 283. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5877-0_70

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-5877-0_70

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-5879-4

  • Online ISBN: 978-1-4684-5877-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation