Methyleugenol hepatocellular cancer initiating effects in rat liver

Food and Chemical Toxicology

Volumn 53, Issue , 2013, Pages 187-196

  Williams, Gary M ^a   Iatropoulos, Michael J ^a   Jeffrey, Alan M ^a   Duan, Jian Dong ^a  

^a NEW YORK MEDICAL COLLEGE   (United States)

Author keywords

DNA adducts; Hepatocarcinogenesis; Methyleugenol; Phenobarbital; Rat

Indexed keywords

CYCLINE; DNA; GLUTATHIONE TRANSFERASE; METHYLEUGENOL; PHENOBARBITAL;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOASSAY; CELL DIVISION; CELL PROLIFERATION; CONTROLLED STUDY; DNA ADDUCT; DNA MODIFICATION; ENVIRONMENTAL TEMPERATURE; HUMIDITY; IMMUNOHISTOCHEMISTRY; INCIDENCE; LIVER CARCINOGENESIS; LIVER CELL CARCINOMA; LIVER TUMOR; MALE; MORPHOLOGY; NONHUMAN; RAT;

RATTUS; RODENTIA;

EID: 84871738383     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2012.11.050     Document Type: Article

References (56)

1. Abdo K.M., Cunningham M.L., Snell M.S., Herbert R.A., Travlos G.S., Eldridge S.R., Bucher J.R. 14-Week toxicity and cell proliferation of methyleugenol administered by gavage to F344 rats and B6C3F1 mice. Food Chem. Toxicol. 2001, 39:303-316.
2. Analytics Historical Control Data, 2010. Anilytics Inc., Gaithersburg, MD, USA.
3. Bannasch P. Preneoplastic lesions as end points in carcinogenicity testing. I. Hepatic preneoplasia. Carcinogenesis 1986, 7:689-695.
4. Boberg E.W., Miller E.D., Miller J.A., Poland A., Liem A. Strong evidence from studies with brachymorphic mice and pentachlorophenol that 1'-sulfoöxysafrole is the major ultimate electrophilic and carcinogenic metabolite of 1'-hydroxysafrole in mouse liver. Cancer Res. 1983, 43:5163-5173.
5. Burkey J.L., Sauer J.M., McQueen C.A., Sipes I.G. Cytotoxicity and genotoxicity of methyleugenol and related congeners - a mechanism of activation for methyleugenol. Mutat. Res. 2000, 453:25-33.
6. Carthew P., Lee P.N., Edwards R.E., Heydon R.T., Nolan B.M., Martin E.A. Cumulative exposure of Tamoxifen: DNA adducts and liver cancer in the rat. Arch. Toxicol. 2001, 75:375-380.
7. Craddock V.M. Effect of a single treatment with the alkylating carcinogens dimethylnitrosamine, diethylnitrosamine and methyl methanesulphonate, on liver regeneration after partial hepatectomy. I. test for induction of liver carcinomas. Chem. Biol. Interact. 1975, 10:313-321.
8. Ding W., Levy D.D., Bishop M.E., Lascelles E., Lyn-Cook Lascelles E., Kulkarri R., Chang C.-W., Aidoo A., Manjanalha M.G. Methyleugenol genotoxicity in the Fischer 344 rat using the comet assay and pathway-focused gene expression profiling. Toxicol. Sci. 2011, 123:103-112.
9. Enzmann H., Bomhard E., Iatropoulos M.J., Ahr H.J., Schlueter G., Williams G.M. Short- and intermediate-term carcinogenicity testing - a review: Part 1 - The prototypes mouse skin tumour assay and rat liver focus. Food Chem. Toxicol. 1998, 36:979-995.
10. Gardner I., Bergin P., Stening P., Kenna J.G., Caldwel J. Immunochemical detection of covalently modified protein adducts in livers of rats treated with methyleugenol. Crit. Rev. Toxicol. 1996, 9:713-721.
11. Greaves P. Liver and Pancreas. Histopathology of Preclinical Toxicity Studies 2007, 457-504. Elsevier, New York, NY, USA.
12. Groh I.A., Cartus A.T., Vallicotti S., Kajzar J., Merz K.-H., Schrenk D., Esselen M. Genotoxic potential of methyleugenol and selected methyleugenol metabolites in cultures Chinese hamster V79 cells. Food Funct. 2012, 3:428-436.
13. Herbert R.A., Abdo K. Methyleugenol. Predictive Value of Rodent Forestomach and Gastric Neuroendocrine Tumours in Evaluating Carcinogenic Risks to Humans. Technical Publication No. 39 2003, 143-158. International Agency for Research on Cancer, Lyon, France.
14. Hong S.P., Fuciarelli A.F., Johnson J.D., Graves S.W., Bates D.J., Waidyanatha S., Smith C.S. Toxicokinetics of methyleugenol in F344 rats and B6C3F1 mice. Xenobiotica 2012, 1-10. (Epub ahead of print).
15. Howes A.J., Chan V.S., Caldwell J. Structure-specificity of the genotoxicity of some naturally occurring alkenylbenzenes determined by the unscheduled DNA synthesis assay in rat hepatocytes. Food Chem. Toxicol. 1990, 28:537-542.
16. Iatropoulos M.J., Williams G.M. Proliferation markers. Exp. Toxicol. Pathol. 1996, 48:175-181.
17. Jeffrey A.M., Luo F.I.Q., Amin S., Krzeminski J., Zech K., Williams G.M. Lack of DNA binding on the rat nasal mucosa and other tissues of the nasal toxicants roflumilast, a phosphodiesterase 4 inhibitor, and a metabolite, 4-amino-3,5-dichloropyridine, in contrast to the nasal carcinogen 2,6-dimethylaniline. Drug Chem. Toxicol. 2002, 25:93-107.
18. 32P-postlabeled DNA-aromatic carcinogen adducts. Anal. Biochem. 1988, 174:381-392.
19. Li D.H., Xu D.C., Randerath K. Species and tissue specificities of I-compounds as contrasted with carcinogen adducts in liver, kidney and skin DNA of Sprague-Dawley rats, ICR mice and Syrian hamsters. Carcinogenesis 1990, 11:2227-2232.
20. Loeb W.F., Quimby F.W. The Clinical Chemistry of Laboratory Animals 1999, Taylor and Francis, Philadelphia, PA, USA, pp. 33-48, 503-513. second ed.
21. Marquardt H., Sternberg S.S., Philips F.S. 7,12-Dimethylbenz(a)anthracene and hepatic neoplasia in regenerating liver. Chem. Biol. Interact. 1970, 2:401-403.
22. Matthews D.E., Battezzati A. Substrate kinetics and catabolic hormones. Organ Metabolism and Nutrition 1994, 1-23. Raven Press, New York. J.M. Kinney, H.M. Tucker (Eds.).
23. National Toxicology Program, NTP., 2000. NTP Toxicology and carcinogenesis studies of methyleugenol (CAS No. 93-15-2) in F344/N rats and B6C3F1 mice (gavage studies). NTP Rep. Ser., 491. National Toxicology Program. Research Triangle Park, NC.
24. Nicholls I., Kolopp M.N., Pommier F., Scheiwiller M. The presence of drug in control samples during toxicokinetic investigations - a Novartis perspective. Regul. Toxicol. Pharm. 2005, 42:172-178.
25. Paini A., Scholz G., Marin-Kuan M., Schilter B., O'Brien J., van Bladeren P.J., Rietjens I.M. Quantitative comparison between in vivo DNA adduct formation from exposure to selected DNA-reactive carcinogens, natural background levels of DNA adduct formation and tumour incidence in rodent bioassays. Mutagenesis 2011, 26:605-618.
26. 1 mice. Carcinogenesis (Lond.) 1984, 5:1623-1628.
27. Punt A., Freidig A.P., Delatour T., Scholz G., Boersma M.G., Schilter B., van Bladeren P.J., Rietjens I.M. A physiologically based biokinetic (PBBK) model for estragole bioactivation and detoxification in rat. Toxicol. Appl. Pharmacol. 2008, 231:248-259.
28. Punt A., Paini A., Boersma M.G., Freidig A.P., Delatour T., Scholz G., Schilter B., van Bladeren P.J., Rietjens I.M. Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared with male rats. Toxicol. Sci. 2009, 110:255-259.
29. Qiagen, (2001) QIAGEN Genomic DNA Handbook.
30. 32P-postlabeling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. I. Adult female CD-1 mice. Carcinogenesis 1984, 5:1613-1622.
31. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis 1986, 7:1543-1551.
32. Rietjens I.M.C.M., Boersma M.G., Van Der Woude H., Jeurissen S.M.F., Schutte M.E., Alink G.M. Flavonoids and alkenylbenzenes: mechanisms of mutagenic action and carcinogenic risk. Mutat. Res. 2005, 574:124-138.
33. 14C]-labeled trans-anethole, estragole and p-proylanisole in human volunteers. Xenobiotica 1987, 17:1223-1232.
34. Sato K., Kitahara A., Satoh K., Ishikawa T., Tatematsu M., Ito N. The placental form of glutathione S-transferase as a new marker protein for preneoplasia in rat chemical hepatocarcinogenesis. GANN 1984, 75:199-202.
35. Smith R.L., Adams T.B., Doull J., Feron V.J., Goodman J.I., Marnett L.J., Portoghese P.S., Waddell W.J., Wagner B.M., Rogers A.E., Caldwell J., Sipes I.G. Safety assessment of allylalkoxybenzene derivatives used as flavouring substances - methyl eugenol and estragole. Food Chem. Toxicol. 2002, 40:851-870.
36. Smith B., Cadby P., Leblanc J.-C., Setzer R.W. Application of the margin of exposure (MoE) approach to substances in food that are genotoxic and carcinogenic. Example: methyleugenol, CASRN:93-15-2. Food Chem. Toxicol. 2010, 48:S89-S97.
37. Stening P., Gardner I., Kenna J.G., Coughtric M.W.H., Caldwell J. Formation of alkenylbenzene macromolecular adducts in human fibroblast V79 cells transfected with human sulfotransferases. Hum. Exp. Toxicol. 1997, 16:62. (abstract only).
38. Swenberg J.A., Richardson F.C., Boucheron J., Dyroff M.C. Relationships between DNA adduct formation and carcinogenesis. Environ. Health Perspect. 1985, 62:177-183.
39. Systat Software Manual, 2004. Systat Software Inc., Chicago, IL, USA.
40. Tanaka T., Mori H., Hirota N., Furuya K., Williams G.M. Effect of DNA synthesis on induction of preneoplastic and neoplastic lesions in rat liver by a single dose of methylazoxymethanol acetate. Chem. Biol. Interact. 1986, 58:13-27.
41. Tong C., Fazio M., Williams G.M. Cell cycle-specific mutagenesis at the hypoxanthine phosphoribosyl-transferase locus in adult rat liver epithelial cells. Proc. Natl. Acad. Sci. 1980, 77:7377-7379.
42. Verna L., Whysner J., Williams G.M. 2-Acetylaminofluorene mechanistic data and risk assessment: DNA reactivity, enhanced cell proliferation and tumor initiation. Pharmacol. Ther. 1996, 71:83-106.
43. Whysner J., Ross P.M., Williams G.M. Phenobarbital mechanistic data and risk assessment: enzyme induction, enhanced call proliferation, and tumor promotion. Pharmacol. Ther. 1996, 71:153-199.
44. Williams G.M. The pathogenesis of rat liver cancer caused by chemical carcinogens. Biochim. Biophys. Acta 1980, 605:167-189.
45. Williams G.M. Phenotypic properties of preneoplastic rat liver lesions and applications to detection of carcinogens and tumor promoters. Toxicol. Pathol. 1982, 10:3-10.
46. Williams G.M. The significance of chemical-induced hepatocellular altered foci in rat liver and application to carcinogen detection. Toxicol. Pathol. 1989, 17:663-674.
47. Williams G.M. Chemically induced rodent preneoplastic lesions as indicators of carcinogenic activity. The Use of Short-and Medium-term Tests for Carcinogens and Data on Genetic Effects in Carcinogenic Hazard Evaluation. Scientific Publications No. 146 1999, 185-202. International Agency for Research on Cancer, Lyon, France. D.B. McGregor, J.M. Rice, S. Venitt (Eds.).
48. Williams G.M., Iatropoulos M.J. Alteration of liver cell function and proliferation: differentiation between adaptation and toxicity. Toxicol. Pathol. 2002, 30:41-53.
49. Williams G.M., Mattia A. Alkoxy-substituted Allylbenzenes Present in Foods and Essential Oils and Used as Flavouring Agents 2009, WHO/FAO Joint Expert Committee on Food Additives (JECFA).
50. Williams G.M., Gebhardt R., Shirma H., Stenbäck F. Non-linearity of neoplastic conversion induced in rat liver by low exposures to diethylnitrosamine. Carcinogenesis 1993, 14:2149-2156.
51. Williams G.M., Iatropoulos M.J., Wang C.X., Jeffrey A.M., Thompson S., Pittman B., Palasch M., Gebhardt R. Non-linearities in 2-acetylaminofluorene exposure-responses for genotoxic and epigenetic effects leading to initiation of carcinogenesis in rat liver. Toxicol. Sci. 1998, 45:152-161.
52. Williams G.M., Iatropoulos M.J., Jeffrey A.M. Thresholds for the effects of 2-acetylaminofluorene in rat liver. Toxicol. Pathol. 2004, 32:85-91.
53. Wislocki P.G., Miller E.C., Miller J.A., McCoy E.C., Rosenkranz H.S. Carcinogenic and mutagenic activities of safrole, 1'-hydroxysafrole, and some known or possible metabolites. Cancer Res. 1977, 37:1883-1891.
54. Zangouras A., Caldwell J., Hutt A.J., Smith R.L. Dose dependent conversion of estragole in the rat and mouse to the carcinogenic metabolite, 1'-hydroxyestragole. Biochem. Pharmacol. 1981, 30:1383-1386.
55. Zhou B.D., Hernandez N.S., Randerath E., Randerath K. Acute elevation by short-term dietary restriction or food deprivation of type II-compound levels in rat liver DNA. Nutr. Cancer 1999, 35:87-95.
56. Zhou G.D., Moorthy B., Bi J., Donnelly K.C., Randerath K. DNA adducts from alkoxyallylbenzenes, herb and spice constituents in cultured human (HepG2) cells. Environ. Mol. Mutagen. 2007, 48:715-721.