Inhibitory effects of naturally occurring coumarins on the metabolic activation of benzo[a]]pyrene and 7,12-dimethylbenz[a]]anthracene in cultured mouse keratinocytes

Carcinogenesis

Volumn 18, Issue 1, 1997, Pages 215-222

  Cai, Yingna ^a   Baer Dubowska, Wanda ^a   Ashwood Smith, Mike ^b   DiGiovanni, John ^a  

^a UNIVERSITY OF TEXAS   (United States)

^b UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

7,12 DIMETHYLBENZ[A]ANTHRACENE; BENZO[A]PYRENE; BORONIC ACID DERIVATIVE; COUMARIN DERIVATIVE; CYTOCHROME P450 INHIBITOR; DIMETHYLBENZ[A]ANTHRACENE; ISOIMPERATORIN; PENTOSALEN; UNSPECIFIC MONOOXYGENASE;

ANIMAL CELL; ARTICLE; CHROMATOGRAPHY; CONTROLLED STUDY; KERATINOCYTE; METABOLIC ACTIVATION; MOUSE; NONHUMAN; PRIORITY JOURNAL;

9,10-DIMETHYL-1,2-BENZANTHRACENE; ANIMALS; BENZO(A)PYRENE; BIOTRANSFORMATION; CARCINOGENS; CELL LINE; COUMARINS; DNA ADDUCTS; FEMALE; HUMANS; KERATINOCYTES; MICE; PSORALENS;

EID: 0031431884     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/18.1.215     Document Type: Article

References (51)

1. Partanen,T. and Boffetta,P. (1994) Cancer risk in asphalt workers and roofers: review and meta-analysis of epidemologic studies. Am. J. Ind. Med., 26, 721-740.
2. Nadon,L., Siemiatycki,J., Dewar,R., Krewski,D. and Gerin,M. (1995) Cancer risk due to occupational exposure to polycyclic aromatic hydrocarbons. Am. J. Ind. Med., 28, 303-324.
3. Heinrich,U., Roller,M. and Pott,F. (1994) Estimation of a lifetime unit lung cancer risk for benzo[a]pyrene based on tumor rates in rats exposed to coal tar/pitch condensation aerosol. Toxicol. Lett., 72, 155-161.
4. Kriek,E., Van Schooten,F.J., Hillebrand,M.J., Van Leeuwen,F.E., Den Engelse,L., De Looff,A.J. and Dijkmans,A.P. (1993) DNA adducts as a measure of lung cancer risk in humans exposed to polycyclic aromatic hydrocarbons. Environ. Health Persp., 99, 71-75.
5. Wood,A.W., Levin,W., Chang,R.L., Yagi,H., Thakker,D.R., Lehr,R.E., Jerina,D.M. and Conney,A.H. (1979) Bay-region activation of carcinogenic polycyclic hydrocarbons. In Jones,P.W. and Lebe,P. (eds) Polynuclear Aromatic Hydrocarbons. Ann Arbor Science Publishers, Michigan, pp. 531-551.
6. DiGiovanni,J. (1989) Metabolism of polycyclic aromatic hydrocarbons and phorbol esters by mouse skin. Relevance to mechanism of action and trans-species/strain carcinogenesis. In Progress in Clinical and Biological Research. Skin Carcinogenesis: Mechanisms and Human Relevance. Alan R. Liss, New York, Vol. 298, pp. 167-199.
7. Ashurst,S.W., Cohen,G.M., Nesnow,S., DiGiovanni,J. and Slaga,T.J. (1983) Formation of benzo[a]pyrene/DNA adducts and their relationship to tumor initiation in mouse epidermis. Cancer Res., 43, 1024-1029.
8. Slaga,T.J. and Boutwell,R.K. (1977) Inhibition of the tumor-initiating ability of the potent carcinogen 7,12-dimethylbenz[a]anthracene by the weak tumor initiator 1,2,3,4-dibenzanthracene. Cancer Res., 37, 128-133.
9. Hall,M. and Grover,P.L. (1990) Polycyclic aromatic hydrocarbons metabolism, activation and tumor initiation. In Cooper,C.S. and Grover,P.L. (eds) Handbook of Experimental Pharmacology. Springer-Verlag, New York, Vol 94/I, pp. 327-372.
10. Dipple,A., Pigott,M., Moschel,R.C. and Constantino,N. (1983) Evidence that binding of 7,12-dimethylbenz[a]anthracene to DNA in mouse embryo cell cultures results in extensive substitution of both adenine and guanine residues. Cancer Res., 43, 4132-4135.
11. Bigger,C.H.A., Sawicki,J.T., Blake,D.M., Raymound,L.G. and Dipple,A. (1983) Products of binding of 7,12-dimethylbenz[a]anthracene to DNA in mouse skin. Cancer Res., 43, 5647-5651.
12. Nesnow,S., Ross,J.A., Stoner,G.D., Mass,M.J. (1995) Mechanistic linkage between DNA adducts, mutations in oncogenes and tumorigenesis of carcinogenic environmental polycyclic aromatic hydrocarbons in strain A/ J mice. Toxicol., 105, 403-413.
13. DiGiovanni,J., Fisher,E.P., Aalfs,K.K. and Prichett,W.P. (1985) Covalent binding of 7,12-dimethylbenz[a]anthracene and 10-fluoro-7,12-dimethyl-benz[a]anthracene to mouse epidermal DNA and its relationship to tumor initiating activity. Cancer Res., 45, 591-597.
14. Rojas,M., Camus,A.M., Alexandrov,K., Husgafvel-Pursiainen,K., Anttila,S., Vainio,H. and Bartsch,H. (1992) Stereoselective metabolism of (-)-benzo[a]pyrene-7,8-diol by human lung microsomes and peripheral blood lymphocytes: effect of smoking. Carcinogenesis, 13, 929-933.
15. Degawa,M., Stern,S.J., Martin,M.V., Guengerich,F.P., Fu,P.P., Ilett,K.F., Kaderlik,R.K. and Kadlubar,F.F. (1994) Metabolic activation and carcinogen-DNA adduct detection in human larynx. Cancer Res., 54, 4915-4919.
16. Shou,M., Korzekwa,K.R., Crespi,C.L., Gonzales,F.J. and Gelboin,H.V. (1994) The role of 12 cDNA-expressed human, rodent, and rabbit cytochrome P450 in the metabolism of benzo[a]pyrene and benzo[a]pyrene trans-7,8-dihydrodiol. Mol. Carcinogenesis, 10, 159-168.
17. Pottenger,L.H. and Jefcoate,C.R. (1990) Characterization of a novel cytochrome P450 from the transformable cell line, C3H/10T1/2. Carcinogenesis, 11, 321-327.
18. Morrison,V.M., Burnett,A.K. and Craft,J.A. (1991) Metabolism of 7,12-dimethylbenz[a]anthracene in hepatic microsomal membranes from rats treated with isozyme-selective inducers of cytochrome P450. Biochem. Pharmacol., 41, 1505-1512.
19. Shimada,T., Hayes,C.L., Yamazaki,H., Amin,S., Hecht,S.S., Guengerich,F.P. and Sutter,T.R. (1996) Activation of chemically diverse procarcinogens by human cytochrome P-450 1B1. Cancer Res., 56, 2979-2984.
20. Hopkins,N.E., Foroozesh,M.K. and Alworth,W.L. (1992) Suicide inhibitors of cytochrome P450 1A1 and 2B1. Biochem. Pharmacol., 44, 787-796.
21. Brake,P.B. and Jefcoate,C.R. (1995) Regulation of cytochrome P450 1B1 in cultured rat adrenocortical cells by cyclic adenosine 3′,5′-monophosphate and 2,3,7,8-tetrachlorodibenzo-p-dioxin. Endocrin., 136, 5034-5041.
22. Alworth,W.L., Viaje,A., Sandoval,A., Warren,B.S. and Slaga,T.J. (1991) Potent inhibitory effects of suicide inhibitors of P450 isozymes on 7, 12-dimethylbenz[a]anthracene and benzo[a]pyrene initiated skin tumors. Carcinogenesis, 12, 1209-1215.
23. Brady,J.F., Ishizaki,H., Fukuto,J.M., Lin,M.C., Fadel,A., Gapae,J.M. and Yang,C.S. (1991) Inhibition of cytochrome P450 IIE1 by diallyl sulfide and its metabolites. Chem. Res. Toxicol., 4, 642-647.
24. Smith,T.J., Guo,Z., Li,C., Ning,S.M., Thomas,P.E. and Yang,C.S. (1993) mechanisms of inhibition of 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone (NNK) bioactivation in mouse by dietary phenethyl isothiocyanate. Cancer Res., 53, 3276-3282.
25. Wargovich,M.J. (1987) Diallyl sulfide, a flavor component of garlic (Allium Sativum), inhibits dimethylhydrazine-induced colon cancer. Carcinogenesis, 8, 487-489.
26. Hayes,M.A., Rushmore,T.H. and Goldberg,M.T. (1987) Inhibition of hepatocarcinogenic responses to 1, 2-dimethylhydrazine by diallyl sulfide, a component of garlic oil. Carcinogenesis, 8, 1155-1157.
27. 6-methylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylnitroamine)-l-(3-pyridyl)-l-butanone in A/J mouse lung. Cancer Res., 49, 2894-2897.
28. Cai,Y., Bennett,D., Nair,R.V., Ceska,O., Ashwood-Smith,M. and DiGiovanni,J. (1993) Inhibition and inactivation of murine hepatic ethoxyand pentoxyresorufin O-dealkylase by naturally occurring coumarins. Chem. Res. Toxicol., 6, 872-879.
29. Cai,Y., Baer-Dubowska,W., Ashwood-Smith,M.J., Ceska,O., Tachibana,S. and DiGiovanni,J. (1996) Mechanism-based inactivation of hepatic ethoxyresorufin O-dealkylation activity by naturally occurring coumarins. Chem. Res. Toxicol., 9, 729-736.
30. Wall,M.E., Wani,M.C., Hughes,T.J. and Taylor,H. (1990) Plant antimutagens, In Kuroda,Y., Shankel,D.M. and Walters,M.D. (eds) Antimutagenesis and Anticarcinogenesis Mechanism II. Plenum Press, New York, pp. 61-78.
31. Ceska,O., Chandhary,S.K., Warrington,P., Ashwood-Smith,M.J., Bushnell,G.W. and Poulton,G.A. (1988) Coriandrin, a novel highly photoactive compound isolated from Coriandrum Sativum. Phytochem., 27, 2083-2087.
32. DiGiovanni,J., Gill,R.D., Nettikumara,A.N., Cilby,A.B. and Reiners,J.J.,Jr (1989) Effect of extracellular calcium concentration on the metabolism of polycyclic aromatic hydrocarbons by cultured mouse keratinocytes. Cancer Res., 49, 5567-5574.
33. Sawer,T.W., Gill,R.D., Smith-Oliver,T., Butterworth,B.E. and DiGiovanni,J. (1988) Measurement of unscheduled DNA synthesis in primary cultures of adult mouse epidermal keratinocytes. Carcinogenesis, 9, 1197-1202.
34. DiGiovanni,J., Miller,D.R., Singer,J., Viaje,A., Fisher,S.M. and Slaga,T.J. (1982) Benzo[a]pyrene metabolism in primary cultures of mouse epidermal cells and untransformed and transformed epidermal cell lines. Cancer Res., 42, 2579-2586.
35. Baer-Dubowska,W., Nair,R.V., Cortez,C., Harvey,R.G. and DiGiovanni,J. (1995) Covalent DNA adducts formation in mouse epidermis from dibenz[a,j]anthracene: evidence for the formation of polar adducts. Chem. Res. Toxicol., 8, 292-301.
36. Baird,W.M. and Brookes,P. (1973) Studies on the formation of hydrocarbondeoxyribonucleoside products by the binding of derivatives of 7-methylbenz[a]anthracene to DNA in aqueous solution in mouse embryo cells in culture. Cancer Res., 33, 2378-2385.
37. Sawicki,J.T., Moschel,R.C. and Dipple,A. (1983) Involvement of both syn- and anti-dihydrodiol-epoxide in the binding of 7,12-dimethyl-benz[a]anthracene to DNA in mouse embryo cells. Cancer Res., 43, 3212-3218.
38. Viswanathan,T. and Alworth,W.L. (1981) Effect of 1-arylpyrroles and napthoflavones upon cytochrome P450 dependent monooxygenase activities. J. Med. Chem., 24, 822-830.
39. Gelboin,H.V., West,D., Gozukara,E., Natori,S., Nagao,M. and Sugimura,T. (1981) (-)-Maackiaim acetate specifically inhibits different forms of aryl hydrocarbon hydroxylase in rat and man. Nature, 291, 659-661.
40. 2+ concentration. PNAS., 87, 1825-1829.
41. Reiners,J.J.,Jr., Cantu,A.R. and Pavone,A. (1991) Distribution of constitutive and polycyclic aromatic hydrocarbon-induced cytochrome P450 activities in murine epidermal cells that differ in their stages of differentiation. Prog. Clin. Biol. Res., 369, 123-135.
42. McCord,A., Burnett,A.K., Wolf,C.R., Morrison,V. and Craft,J.A. (1988) Role of specific cytochrome P450 isozymes in the regio-selective metabolism of 7, 12-dimethylbenz[a]anthracene in microsomes from rats treated with phenobarbital or Sudan III. Carcinogenesis, 9, 1485-1491.
43. 32P-postlabeling technique. Carcinogenesis, 7, 535-540.
44. Sutter,T.R., Guzman,K., Dold,K.M. and Greenlee,W.F. (1991) Targets for dioxin: genes for plasminogen activator inhibitor-2 and interleukin-1 beta. Science, 254, 415-418.
45. Reiners,J.,Jr. (1996) Personal communication.
46. Agarwal,R., Jugert,F.K., Khan,S.G., Bickers,D.R., Merk,H.F. and Mukhtar,H. (1994) Evidence for multiple inducible cytochrome P450 isozymes in SENCAR mouse skin by pyridine. Biochem. Biophys. Res. Commun., 199, 1400-1406.
47. Jugert,F.K., Agarwal,R., Kuhn,A., Bickers,D.R., Merk,H.F. and Mukhtar,H. (1994) Multiple cytochrome P450 isozymes in murine skin: induction of P450 1A, 2B, 2E, and 3A by dexamethasone. J. Invest. Dermatol., 102, 970-975.
48. 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.
49. Vericat,J.A., Cheng,S.C. and Dipple,A. (1991) Absolute configuration of 7,12-dimethylbenz[a]anthracene-DNA adducts in mouse epidermis. Cancer Lett., 57, 237-242.
50. Lau,H.H.S., Coffing,S.L., Lee,H., Harvey,R.G. and Baird,W.M. (1995) Stereoselectivity of activation of 7,12-dimethylbenz[a]anthracene-3,4-dihydrodiol to the anti-diol epoxide metabolite in a human mammary carcinomas MCF-7 cell-mediated V79 cell mutation assay. Chem. Res. Toxicol., 8, 970-978.
51. Christou,M., Savas,U., Spink,D.C., Gierthy,J.F. and Jefcoate,C.R. (1994) Co-expression of human CYP 1A1 and a human analog of cytochrome P450-EF in response to 2,3,7,8-tetrachlorodibenzo-p-dioxin in the human mammary carcinoma-derived MCF-7 cells. Carcinogenesis, 15, 725-732.