Expression of human glutathione S-transferase P1 confers resistance to benzo[a]pyrene or benzo[a]pyrene-7,8-dihydrodiol mutagenesis, macromolecular alkylation and formation of stable N2-Gua-BPDE adducts in stably transfected V79MZ cells co-expressing hCYP1A1

Carcinogenesis

Volumn 28, Issue 1, 2007, Pages 207-214

  Kushman, Mary E ^a   Kabler, Sandra L ^a   Fleming, Melissa H ^a   Ravoori, Srivani ^b   Gupta, Ramesh C ^b   Doehmer, Johannes ^c   Morrow, Charles S ^a   Townsend, Alan J ^a  

^a WAKE FOREST SCHOOL OF MEDICINE   (United States)

^b University of Louisville School of Medicine   (United States)

^c Gen Pharm Tox   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

7,8 DIHYDRO 7,8 DIHYDROXYBENZO[A]PYRENE; 7,8 DIHYDROXYBENZO[A]PYRENE 9,10 OXIDE; BENZO[A]PYRENE; CYTOCHROME P450 1A1; GLUTATHIONE TRANSFERASE P1; PHOSPHORUS 32; TRITIUM;

ALKYLATION; ANIMAL CELL; ARTICLE; CELL STRAIN V 79; CONCENTRATION RESPONSE; CONTROLLED STUDY; CORRELATION ANALYSIS; DETOXIFICATION; DNA ADDUCT; DNA BINDING; DNA ISOLATION; ENANTIOMER; GENE LOCUS; GENETIC TRANSFECTION; GENOTOXICITY; HUMAN; INCUBATION TIME; MACROMOLECULE; METABOLITE; MUTAGENESIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION;

7,8-DIHYDRO-7,8-DIHYDROXYBENZO(A)PYRENE 9,10-OXIDE; ALKYLATION; ANIMALS; BENZO(A)PYRENE; CELLS, CULTURED; CRICETINAE; CRICETULUS; CYTOCHROME P-450 CYP1A1; DNA ADDUCTS; DNA DAMAGE; GLUTATHIONE S-TRANSFERASE PI; HUMANS; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; MUTAGENESIS; MUTAGENS; TRANSFECTION;

EID: 33845637348     PISSN: 01433334     EISSN: 14602180     Source Type: Journal    
DOI: 10.1093/carcin/bgl125     Document Type: Article

References (31)

1. Sims,P., Grover,P.L., Swaisland,A., Pal,K. and Hewer,A. (1974) Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide. Nature, 252, 326-328.
2. Talalay,P., Fahey,J.W., Holtzclaw,W.D., Prestera,T. and Zhang,Y. (1995) Chemoprotection against cancer by phase 2 enzyme induction. [Review] [36 refs]. Toxicol. Lett., 82-83, 173-179.
3. Ishikawa,T. (1992) The ATP-dependent glutathione S-conjugate export pump [see comments]. Trends Biochem. Sci., 17, 463-468.
4. Morrow,C.S., DiahS., Smitherman,P.K., Schneider,E. and Townsend,A.J. (1998) Multidrug resistance protein and glutathione S-transferase P1-1 act in synergy to confer protection from 4-nitroquinoline 1-oxide toxicity. Carcinogenesis, 19, 109-115.
5. Conney,A.H. (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture. [Review] [366 refs]. Cancer Res., 42, 4875-4917.
6. Yang,S. (1988) Sterroselectivity of cytochrome P-450 isozymes and epoxide hydrolase in the metabolism of polycyclic aromatic hydrocarbons. Biochem. Pharmacol., 37, 61-70.
7. Jernstrom,B., Dock,L. and Martinez,M. (1984) Metabolic activation of benzo[alpyrene-7,8-dihydrodiol and benzo[alpyrene-7,8-dihydrodiol-9,10-epoxide to protein-binding products and the inhibitory effect of glutathione and cysteine. Carcinogenesis, 5, 199-204.
8. Jernstrom,B. and Graslund,A. (1994) Covalent binding of benzo[a]pyrene 7,8-dihydrodiol 9,10-epoxides to DNA: Molecular structures, induced mutations and biological consequences. [Review]. Biophys. Chem., 49, 185-199.
9. Jernstrom,B., Martinez,M., Meyer,D.J. and Ketterer,B. (1985) Glutathione conjugation of the carcinogenic and mutagenic electrophile (+/-)-7 beta, 8 alpha-dihydroxy-9 alpha, 10 alpha-oxy-7,8,9,10-tetra hydrobenzo[a]-pyrene catalyzed by purified rat liver glutathione transferases. Carcinogenesis, 6, 85-89.
10. Hayes,J.D. and Pulford,D.J. (1995) The glutathione S-transferase supergene family: Regulation of GST and the contribution of the isoenzymes to cancer chemoprotection and drug resistance. Crit. Rev. Biochem. Mol. Biol., 30, 445-600.
11. Ketterer,B. (1988) Protective role of glutathione and glutathione transferases in mutagenesis and carcinogenesis. [Review]. Mutat. Res., 202, 343-361.
12. Sundberg,K., Dreij,K., Seidel,A. and Jernstrom,B. (2002) Glutathione conjugation and DNA adduct formation of dibenzo[a,l]pyrene and benzo[a]pyrene diol epoxides in V79 cells stably expressing different human glutathione transferases. Chem. Res. Toxicol., 15, 170-179.
13. Fields,W.R., Li,Y. and Townsend,A.J. (1994) Protection by transfected glutathione S-transferase isozymes against carcinogen-induced alkylation of cellular macromolecules in human MCF-7 cells. Carcinogenesis, 15, 1155-1160.
14. Townsend,A.J., Fields,W.R., Haynes,R.L., Karper,A.J., Li,Y., Doehmer,J. and Morrow,C.S. (1998) Chemoprotective functions of glutathione S-transferases in cell lines induced to express specific isozymes by stable transfection. Chem. Biol. Interact., 111-112, 389-407.
15. Seidel,A., Friedberg,T., Lollmann,B., Schwierzok,A., Funk,M., Frank,H., Holler,R., Oesch,F. and Glatt,H. (1998) Detoxification of optically active bay- and fjord-region polycyclic aromatic hydrocarbon dihydrodiol epoxides by human glutathione transferase P1-1 expressed in Chinese hamster V79 cells. Carcinogenesis, 19, 1975-1981.
16. Nakajima,T., Elovaara,E., Anttila,S., Hirvonen,A., Camus,A.M., Hayes,J.D., Ketterer,B. and Vainio,H. (1995) Expression and polymorphism of glutathione S-transferase in human lungs: Risk factors in smoking-related lung cancer. Carcinogenesis, 16, 707-711.
17. Harries,L.W., Stubbins,M.J., Forman,D., Howard,G. and Wolf,C.R. (1997) Identification of genetic polymorphisms at the glutathione S-transferase Pi locus and association with susceptibility to bladder, testicular and prostate cancer. Carcinogenesis, 18, 641-644.
18. Schmalix,W.A., Maser,H., Kiefer,F., Reen,R., Wiebel,F.J., Gonzalez,F., Seidel,A., Glatt,H., Greim,H. and Doehmer,J. (1993) Stable expression of human cytochrome P450 1A1 cDNA in V79 Chinese hamster cells and metabolic activation of benzo[a]pyrene. Eur. J. Pharmacol., 248, 251-261.
19. Glatt,H., Gemperlein,I., Turchi,G., Heinritz,H., Doehmer,J. and Oesch,F. (1987) Search for cell culture systems with diverse xenobiotic-metabolizing activities and their use in toxicological studies. [Review]. Mol. Toxicol., 1, 313-334.
20. Habig,W.H. and Jakoby,W.B. (1981) Assays for differentiation of glutathione S-transferases. Methods Enzymol., 77, 398-405.
21. Burke,M.D., Thompson,S., Weaver,R.J., Wolf,C.R. and Mayer,R.T. (1994) Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem. Pharmacol., 48, 923-936.
22. Reddy,M. and Randerath,K. (1986) Nuclease P1-mediated enhancement of sensitivity of 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis, 7, 1543-1551.
23. Reddy,A.P., Pruess,S.D., Ji,C., Gorycki,P. and Marnett,L.J. (1992) 32P-postlabeling analysis of DNA adduction in mouse skin following topical administration of (+)-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene. Chem. Res. Toxicol., 5, 26-33.
24. Swedmark,S., Romert,L., Morgenstern,R. and Jenssen,D. (1992) Studies on glutathione transferases belonging to class pi in cell lines with different capacities for conjugating (+)-7 beta, 8 alpha-dihydroxy-9 alpha, 10 alphaoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. Carcinogenesis, 13, 1719-1723.
25. Wood,A.W., Chang,R.L., Levin,W., Yagi,H., Thakker,D.R., Jerina,D.M. and Conney,A.H. (1977) Differences in mutagenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene 7,8-diol-9,10-epoxides. Biochem. Biophys. Res. Commun., 77, 1389-1396.
26. Chiapperino,D., Kroth,H., Kramarczuk,I.H., Sayer,J.M., Masutani,C., Hanaoka,F., Jerina,D.M. and Cheh,A.M. (2002) Preferential mis-incorporation of purine nucleotides by human DNA polymerase eta opposite benzo[a]pyrene 7,8-diol 9,10-epoxide deoxyguanosine adducts. J. Biol. Chem., 277, 11765-11771.
27. Devanesan,P., Higginbotham,S., Ariese,F., Jankowiak,R., Suh,M., Small,G., Cavalieri,E. and Rogan,E. (1996) Depurinating and stable benzo[al]yrene-DNA adducts formed in isolated rat liver nuclei. Chem. Res. Toxicol., 9, 1113-1116.
28. Driscoll,H.C., Matson,S.W., Sayer,J.M., Kroth,H., Jerina,D.M. and Brosh,R.M.,Jr. (2003) Inhibition of Werner syndrome helicase activity by benzo[c]phenanthrene diol epoxide dA adducts in DNA is both strand- and stereoisomer-dependent. J. Biol. Chem., 278, 41126-41135.
29. Wood,A.W., Chang,R.L., Huang,M.T., Levin,W., Lehr,R.E., Kumar,S., Thakker,D.R., Yagi,H., Jerina,D.M. and Conney,A.H. (1980) Mutagenicity of benzo(e)pyrene and triphenylene tetrahydroepoxides and diolepoxides in bacterial and mammalian cells. Cancer Res., 40, 1985-1989.
30. Buening,M.K., Wislocki,P.G., Levin,W., Yagi,H., Thakker,D.R., Akagi,H., Koreeda,M., Jerina,D.M. and Conney,A.H. (1978) Tumorigenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene 7,8-diol-9,10-epoxides in newborn mice: Exceptional activity of (+)-7 {beta},8alpha-dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. Proc. Natl Acad. Sci. USA, 75, 5358-5361.
31. Jacob,J., Doehmer,J., Grimmer,G., Soballa,V., Raab,G., Seidel,A. and Greim,H. (1996) Metabolism of phenanthrene, benz[a]anthracene, benzo[a]pyrene, and benzo[c]phenanthreine by eight cDNA-expressed human and rat cytochromes. Polycyclic Aromatic Compounds, 10, 1-9.