Inhibition of polycyclic aromatic hydrocarbon-DNA adduct formation in epidermis and lungs of SENCAR mice by naturally occurring plant phenols

Cancer Research

Volumn 47, Issue 3, 1987, Pages 767-773

  Das, Mukul ^b   Khan, Wasiuddin A ^b   Asokan, Parthasarathy ^b   Bickers, David R ^b  

^a LOUIS STOKES CLEVELAND VA MEDICAL CENTER   (United States)

^b UNIVERSITY HOSPITALS OF CLEVELAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBON; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON;

ANIMAL CELL; ANIMAL EXPERIMENT; DNA ADDUCT; EPIDERMIS; LUNG; MOUSE; NONHUMAN; PRIORITY JOURNAL; RESPIRATORY SYSTEM;

ANIMALS; ANTHRAQUINONES; BENZO(A)PYRENE; DNA; FEMALE; FLAVONOIDS; HYDROLYZABLE TANNINS; KINETICS; LUNG; MICE; MICE, INBRED STRAINS; MICROSOMES; PHENOLS; PLANTS; POLYCYCLIC COMPOUNDS; QUERCETIN; SKIN;

EID: 0023139824     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (48)

1. Committee on Biological Effects of Atmospheric Pollutants. Particulate Polycyclic Organic Matter. Washington, DC: National Academy of Sciences, 1972.
2. Boutwell, R. K. The functions and mechanism of promotors of carcinogenesis. CRC Crit. Rev. Toxicol., 2:419-433, 1977.
3. Deutsch-Wengel, R. P., Brune, H., Gimmer, G., Dettbam, G., and Misfeld, J. Experimental studies in rat lungs on the carcinogenicity and dose-response relationships of eight frequently occurring environmental polycyclic aromatic hydrocarbons. J. Natl. Cancer Inst., 71:539-544, 1983.
4. Buening, M. K., Wislocki, P. G., Levin, W., Yagi, H., Thakker, D. R., Akagi, H., Koreeda, M., Jerina, D. M., and Conney, A. H. Tumorigenicity of the optical enantiomers of the diasteromeric benzo(a)pyrene-7,8-diol-9,10-epoxides in newborn mice: exceptional activity of (+)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene. Proc. Natl. Acad. Sci. USA, 75: 5358–5361, 1978.
5. Conney, A. H. 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.
6. Ashurst, S. W., Cohen, G. M., DiGiovanni, J., and Slaga, T. J. Formation of benzo(a)pyrene-DNA adducts and their tumor initiation in mouse epidermis. Cancer Res., 43:1024-1029, 1983.
7. DiGiovanni, J., Sina, J. F., Ashurst, S. W., Singer, J. M., and Diamond, L. Benzo(a)pyrene and 7,12-dimethylbenz(a)anthracene metabolism and DNA adduct formation in primary cultures of hamster epidermal cells. Cancer Res., 43:163-170, 1983.
8. Koreeda, M., Moore, P. D., Wislocki, P. G., Levin, W., Conney, A. H., Yagi, H., and Jerina, D. M. Binding of benzo(a)pyrene-7,8-diol-9,10-epoxides to DNA, RNA and protein of mouse skin occurs with high stereoselectivity. Science (Wash. DC), 199:778-781, 1978.
9. Brookes, P., and Osborne, M. R. Mutation in mammalian cells by stereoisomers of anti-benzo(a)pyrene-diol epoxide in relation to the extent and nature of the DNA reaction products. Carcinogenesis (Lond.), 3:1223-1226, 1983.
10. Buening, M. K., Wislocki, P. G., Levin, W., Yagi, H., Thakker, D. R., Akagi, H., Koreeda, M., Jerina, D. M., and Conney, A. H. Tumorigenicity of the optical enantiomers of the diastereomeric benzo(a)pyrene-7,8-diol-9,10-epoxides in newborn mice; exceptional activity of (+)-7β,8α-dihydroxy-9α, 10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene. Proc. Natl. Acad. Sci. USA, 75: 5358-5361, 1978.
11. Slaga, T. J., Bracken, W. J., Gleason, G., Levin, W., Yagi, H., Jerina, D. M., and Conney, A. H. Marked differences in the skin tumor-initiating activities of the optical enantiomers of the diastereomeric benzo(a)pyrene-7,8-diol-9,10-epoxides. Cancer Res., 39:67-71, 1979.
12. Autrup, H., Harris, C. C., Trump, B. F., and Jeffrey, A. M. Metabolism of benzo(a)pyrene and identification of the major benzo(a)pyrene-DNA adducts in cultured human colon. Cancer Res., 38:3689-3696, 1978.
13. Baird, W. M., and Diamond, L. The nature of benzo(a)pyrene DNA adducts formed in hamster embryo cells depends on the length of time of exposure to benzo(a)pyrene. Biochem. Biophys. Res. Commun., 77:162-167, 1977.
14. Ivanovic, V., Geacintov, N. E., Yamasaki, H., and Weinstein, I. B. DNA and RNA adducts formed in hamster embryo cell cultures exposed to benzo(a)pyrene. Biochemistry, 17:1597-1603, 1978.
15. Nakayama, J., Yuspa, S. H., and Poirier, M. C. Benzo(a)pyrene-DNA adduct formation and removal in mouse epidermis in vivo and in vitro: relationship of DNA binding to initiation of skin carcinogenesis. Cancer Res., 44:4087-4095, 1984.
16. Phillips, D. H., and Sims, P. Polycyclic aromatic hydrocarbon metabolites: their reactions with nucleic acids. In: P. L. Grover (ed.), Chemical Carcinogens and DNA, Vol. 2, pp. 29–57. Boca Raton, FL: CRC Press, Inc., 1978.
17. Mukhtar, H., Das, M., DelTito, B. J., and Bickers, D. R. Epidermal benzo(a)pyrene metabolism and DNA-binding in Balb/C mice: inhibition by ellagic acid. Xenobiotica, 14:527-531, 1984.
18. Shugart, L., and Kao, J. Effect of ellagic and caffeic acids on covalent binding of benzo(a)pyrene to epidermal DNA of mouse skin in organ culture. Int. J. Biochem., 16: 571-573, 1984.
19. Dixit, R., Teel, R. W., Daniel, F. B., and Stoner, G. D. Inhibition of benzo(a)pyrene and benzo(a)pyrene-trans-7,8-diol metabolism and DNA binding in mouse lung explants by ellagic acid. Cancer Res., 45:2951-2956, 1985.
20. Mukhtar, H., DelTito, B. J., Marcelo, C. L., Das, M., and Bickers, D. R. Ellagic acid: a potent inhibitor of benzo(a)pyrene metabolism and its subsequent glucuronidation, sulfation and DNA binding in BALB/C mouse keratinocytes. Carcinogenesis (Lond.), 5: 1565-1571, 1984.
21. Mukhtar, H., Das, M., DelTito, B. J., and Bickers, D. R. Protection against 3-methylcholanthrene-induced skin tumorigenesis in BALB/C mice by ellagic acid. Biochem. Biophys. Res. Commun., 119:751-757, 1984.
22. Lesca, P. Protective effects of ellagic acid and other plant phenols on benzo(a)pyrene-induced neoplasia in mice. Carcinogenesis (Lond.), 4:1651-1653, 1983.
23. Chang, R. L., Huang, M. T., Wood, A. W., Wong, C. Q., Newmark, H. L., Yagi, H., Sayer, J. M., Jerina, D. M., and Conney, A. H. Effect of ellagic acid and hydroxylated flavonoids on the tumorigenicity of benzo(a)pyrene and (±)7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene on mouse skin and in the newborn mouse. Carcinogenesis (Lond.), 6:1127-1133, 1985.
24. Das, M., Mukhtar, H., Bik, D. P., and Bickers, D. R. Inhibition of epidermal xenobiotic metabolism in SENCAR mice by naturally occurring plant phenols. Cancer Res., 47:000-000, 1987.
25. Das, M., Bickers, D. R., and Mukhtar, H. Inhibition of mouse epidermal polycyclic aromatic hydrocarbon metabolism and carcinogenicity by clotrimazole. In: M. Cooke, A. J. Dennis, and G. L. Fisher (eds.), Polynuclear Aromatic Hydrocarbons, pp. 215–227. Columbus, OH: Batelle Press, 1986.
26. Das, M., Bickers, D. R., and Mukhtar, H. Effect of ellagic acid on hepatic and pulmonary xenobiotic metabolism in mice: studies on the mechanism of its anticarcinogenic action. Carcinogenesis (Lond.), 6:1409-1413, 1985.
27. Kates, J., and Beeson, J. Ribonucleic acid synthesis and release of RNA in vaccinia cores. J. Mol. Biol., 50:1-10, 1970.
28. Diamond, L., Defendi, V., and Brookes, P. The initiation of 1,17-dimethyl-benz(a)anthracene with cells sensitive and resistant to toxicity induced by this carcinogen. Cancer Res., 27:891-897, 1967.
29. Ashurst, S. W., and Cohen, G. M. The formation of benzo(a)pyrene-deoxyribonucleoside adducts in vivo and in vitro. Carcinogenesis (Lond.), 3: 267-273,1982.
30. Pulkrabek, P., Leffler, S., Grunberger, D., and Weinstein, I. B. Modification of deoxyribonucleic acid structure and confirmation and effects on transfectional activity. Biochemistry, 18:5128-5134, 1979.
31. Hesse, S., Jernstrom, B., Martinez, M., Moldeus, P., Christodulides, L., and Ketterer, B. Inactivation of DNA-binding metabolites of benzo(a)pyrene and benzo(a)pyrene-7,8-dihydrodiol by glutathione and glutathione-S-transferases. Carcinogenesis (Lond.), 3:757-760, 1982.
32. Lesca, P., Lecointe, P., Paoletti, C., and Mansuy, D. Ellipticines as potent inhibitors of microsome-dependent chemical mutagenesis. Chem.-Biol. Interact, 25:279-286, 1979.
33. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. Protein measurement with the Folin phenol reagent. J. Biol. Chem., 193:265-275, 1951.
34. Cerutti, P. A., Sessions, F., Hariharan, P. V., and Lusby, A. Repair of DNA damage induced by benzo(a)pyrene diol-epoxide I and II in human alveolar tumor cells. Cancer Res. 38:2118-2124, 1978.
35. Yang, L. L., Maher, V. M., and McCormick, J. J. Error free excision of the cytotoxic and mutagenic N2-deoxyguanosine DNA adduct formed in human fibroblasts by [(±)-73,32-dihydroxy-92,102]-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene. Proc. Natl. Acad. Sci. USA, 77 (Suppl. 10): 5933–5937, 1980.
36. Cleaver, J. E. Defective repair replication of DNA in xeroderma pigmentosum. Nature (Lond.), 218:652-656, 1968.
37. Paterson, M. C., Smith, D. P., Lohman, P. H., Anderson, A. K., and Fishman, L. Defective excision repair of x-ray-damaged DNA in human (ataxia telangiectasia) fibroblasts. Nature (Lond.), 260:444-446, 1976.
38. Jeffery, A. M., Weinstein, I. B., Jennette, K. W., Grzeskowiak, K., Nakanishsi, K., Harvey, R. G., Autrup, H., and Harris, C. C. Structure of benzo(a)pyrene nucleic acid adducts formed in human and bovine bronchial explants. Nature (Lond.), 269:348-350, 1977.
39. Eastman, A., and Bresnick, E. Persistent binding of 3-methylcholanthrene to mouse lung DNA and its correlation with susceptibility to pulmonary neoplasia. Cancer Res., 39:2400-2405, 1979.
40. Slaga, T. J., and Bracken, W. M. The effect of antioxidants on skin tumor initiation and aryl hydrocarbon hydroxylase. Cancer Res., 37: 1631–1635, 1977.
41. Huang, M. T., Wood, A. W., Newmark, H. L., Sayer, J. M., Yagi, H., Jerina, D. M., and Conney, A. H. Inhibition of the mutagenicity of bay-region diolepoxides of polycyclic aromatic hydrocarbons by phenolic plant flavonoids. Carcinogenesis (Lond.), 4:1631-1637, 1983.
42. Huang, M. T., Chang, R. L., Wood, A. W., Newmark, H. L., Sayer, J. M., Yagi, H., Jerina, D. M., and Conney, A. H. Inhibition of mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by tannic acid, hydroxylated anthraquinones and hydroxylated cinnamic acid derivatives. Carcinogenesis (Lond.), 6:237-242, 1985.
43. Wood, A. W., Haung, M. T., Chang, R. L., Newmark, H. L., Lehr, R. E., Yagi, H., Sayer, J. M., Jerina, D. W., and Conney, A. H. Inhibition of mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: exceptional activity of ellagic acid. Proc. Natl. Acad. Sci. USA, 79:5513-5517, 1982.
44. DiGiovanni, J., Decina, P. C., Prichett, W. P., Fisher, E. P., and Aalfs, K. K. Formation and disappearance of benzo(a)pyrene DNA-adducts in mouse epidermis. Carcinogenesis (Lond.), 6:741-747, 1985.
45. Kakefuda, T., and Yamamoto, H. A. Modification of DNA by the benzo(a)pyrene metabolite diol epoxide γ-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene. Proc. Natl. Acad. Sci. USA, 75: 415-419,1978.
46. Grunberger, D., and Weinstein, I. B. Conformational changes in nucleic acids modified by chemical carcinogens. In: P. L. Grover (ed.), Chemical Carcinogens and DNA, Vol. 2, pp. 153–201. Boca Raton, FL: CRC Press, Inc., 1979.
47. Wattenberg, L. W. Inhibition of neoplasia by minor dietary constituents. Cancer Res. (Suppl.), 43:2448s-2453s, 1983.
48. Harborne, J. B., Mabry, T. J., and Mabry, H. The Flavonoids, Vols. 1 and 2. New York: Academic Press, 1975.