A physiologically based biodynamic (PBBD) model for estragole DNA binding in rat liver based on in vitro kinetic data and estragole DNA adduct formation in primary hepatocytes

Toxicology and Applied Pharmacology

Volumn 245, Issue 1, 2010, Pages 57-66

  Paini, Alicia ^a,b   Punt, Ans ^a,b   Viton, Florian ^b   Scholz, Gabriele ^b   Delatour, Thierry ^b   Marin Kuan, Maricel ^b   Schilter, Benoît ^b   van Bladeren, Peter J ^a,b   Rietjens, Ivonne M C M ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

1 Hydroxyestragole; Bioactivation; DNA adduct formation; Estragole; Isotope dilution; LC ESI MS MS; Physiologically based biodynamic (PBBD) model; Rat primary hepatocytes

Indexed keywords

1' HYDROXYESTRAGOLE; BIOLOGICAL MARKER; CARCINOGEN; ESTRAGOLE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOASSAY; CARCINOGEN DNA INTERACTION; CARCINOGENESIS; CONTROLLED STUDY; DNA ADDUCT; EXPOSURE; IN VITRO STUDY; LIVER CELL; MALE; MODEL; NONHUMAN; PHYSIOLOGICALLY BASED BIODYNAMIC MODEL; PREDICTION; RAT; TOXICOKINETICS;

ANIMALS; ANISOLES; CARCINOGENS; DNA ADDUCTS; HEPATOCYTES; HUMANS; MALE; MODELS, BIOLOGICAL; MUTAGENICITY TESTS; RATS; RATS, SPRAGUE-DAWLEY;

RATTUS; RODENTIA;

EID: 77952546103     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2010.01.016     Document Type: Article

References (39)

1. Bailey G.S., Reddy A.P., Pereira C.B., Harttig U., Baird W., Spitsbergen J.M., Hendricks J.D., Orner G.A., Williams D.E., Swenberg J.A. Nonlinear cancer response at ultralow dose: a 40800-animal ED001 tumor and biomarker study. Chem. Res. Toxicol. 2009, 22(7):1264-1276.
2. Bignold L.P. Carcinogen-induced impairment of enzymes for replicative fidelity of DNA and the initiation of tumours. Carcinogenesis 2004, 25(3):299-307.
3. Borchert P., Wislocki P.G., Miller J.A., Miller E.C. The metabolism of the naturally occurring hepatocarcinogen safrole to 1′-hydroxysafrole and the electrophilic reactivity of 1′-acetoxysafrole. Cancer Res. 1973, 33:575-589.
4. Bock K.W., Brunner G., Hoensch H., Huber E., Josting D. Determination of microsomal UDP-glucuronyltransferase in needle-biopsy specimens of human liver. Eur. J. Clin. Pharmacol. 1978, 14:367-373.
5. Cavin C., Delatour T., Marin-Kuan M., Holzhäuser D., Higgins L., Bezencon C., Guignard G., Junod S., Richoz-Payot J., Gremaud E., Hayes J.D., Nestler S., Mantle P., Schilter B. Reduction in antioxidant defenses may contribute to ochratoxin a toxicity and carcinogenicity. Toxicol. Sci. 2007, 96(1):30-39.
6. Chan V.S.W., Caldwell J. Comparative induction of unscheduled DNA. synthesis in cultured rat hepatocytes by allylbenzenes and their 10-hydroxy metabolites. Food Chem. Toxicol. 1992, 30:831-836.
7. Coleman M.E., Thran B., Morse S.S., Hugh-Jones M., Massulik S. Inhalation anthrax: dose response and risk analysis. Biosecur. Bioterror. 2008, 6(2):147-159.
8. Conolly R.B., Kimbell J.S., Janszen D., Schlosser P.M., Kalisak D., Preston J., Miller F.J. Biologically motivated computational modeling of formaldehyde carcinogenicity in the F344 rat. Toxicol. Sci. 2003, 75:432-447.
9. Delatour T., Mally A., Richoz J., Ozden S., Dekant W., Ihmels H., Otto D., Gasparutto D., Marin-Kuan M., Schilter B., Cavin C. Absence of 2′-deoxyguanosine-carbon 8-bound ochratoxin A adduct in rat kidney DNA monitored by isotope dilution LC-MS/MS. Mol. Nutr. Food Res. 2008, 52(4):472-482.
10. Delatour T., Hegele J., Parisoda V., Richoza J., Maurera S., Stevenb M., Buetler T. Analysis of advanced glycation endproducts in dairy products by isotope dilution liquid chromatography-electrospray tandem mass spectrometry. The particular case of carboxymethyllysine. J. Chromatogr. A 2009, 1216:2371-2381.
11. Drinkwater N.R., Miller E.C., Miller J.A., Pitot H.C. Hepatocarcinogenicity of estragole (1-allyl-4-methoxybenzene) and 1′-hydroxyestragole in the mouse and mutagenicity of 1′-acetoxyestragole in bacteria. J. Natl. Cancer Inst. 1976, 57:1323-1331.
12. Evans M.V., Andersen M.E. Sensitivity analysis and the design of gas uptake inhalation studies. Inhal. Toxicol. 1995, 7(7):1075-1094.
13. Evans M.V., Andersen M.E. Sensitivity analysis of a physiological model for 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD): assessing the impact of specific model parameters on sequestration in liver and fat in the rat. Toxicol. Sci. 2000, 54:71-80.
14. Farmer P.B. Significance for risk assessment of increases in background levels of carcinogen-derived protein and DNA Adducts. Abstr./Toxicol. Lett. 2008, 180S(2008):S6-S27.
15. Farmer P.B., Brown K., Tompkins E., Emms V.L., Jones D.J.L., Singh R., Phillips D.H. DNA adducts: mass spectrometry methods and future prospects. Toxicol. Appl. Pharmacol. 2005, 207(2005):S293-S301.
16. Gardner I., Wakazono H., Bergin P., de Waziers I., Beaune P., Kenna J.G., Caldwell J. Cytochrome P450 mediated bioactivation of methylglyoxal to 1′-hydroxymethyleugenol in Fischer 344 rat and human liver microsomes. Carcinogenesis 1997, 18:1775-1783.
17. Iyer L.V., Ho M.N., Shinn W.M., Bradford W.W., Tanga M.J., Nath S.S., Green C.E. Glucuronidation of 1-hydroxyestragole (1′-HE) by Human UDP-Glucuronosyltransferases UGT2B7 and UGT1A9. Toxicol. Sci. 2003, 73:36-43.
18. Liao C.M., Liang H.M., Chen B.C., Singh S., Tsai J.W., Chou Y.H., Lin W.T. Dynamical coupling of PBPK/PD and AUC-based toxicity models for arsenic in tilapia Oreochromis mossambicus from blackfoot disease area in Taiwan. Environ. Pollut. 2005, 135(2):221-233.
19. Mager D.E., Woo S., Jusko W.J. Scaling pharmacodynamics from in vitro and preclinical animal studies to humans. Drug Metab. Pharmacokinet. 2009, 24(1):16-24.
20. Miller E.C., Swanson A.B., Phillips D.H., Fletcher T.L., Liem A., Miller J.A. Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Cancer Res. 1983, 43:1124-1134.
21. Phillips D.H. DNA adducts as markers of exposure and risk. Mutation Res. 2005, 577(1-2):284-292.
22. Phillips D.H., Miller J.A., Miller E.C., Adams B. Structures of the DNA adducts formed in mouse liver after administration of the proximate hepatocarcinogen 1′-hydroxyestragole. Cancer Res. 1981, 41:176-186.
23. Preston R.J., Williams G.M. DNA-reactive carcinogens: mode of action and human cancer hazard. Crit Rev. Toxicol. 2005, 35:673-683.
24. Punt A., Delatour T., Scholz G., Schilter B., van Bladeren P.J., Rietjens I.M.C.M. Tamdem mass spectrometry analysis of N2-(trans-isoestragole-3′-yl)deoxyguanosine as a strategy to study species differences in sulfotransferase conversion of the proximate carcinogen 1′-hydroxyestragole. Chem. Res. Tox. 2007, 20(7):991-998.
25. Punt A., Freidig A.P., Delatour T., Scholz G., Schilter B., Boersma M.G., van Bladeren P.J., Rietjens I.M.C.M. A physiologically based biokinetic (PBBK) model for estragole bioactivation and detoxification in rat. Toxicol. Appl. Pharmacol. 2008, 231(2):248-259.
26. Punt A., Paini A., Boersma M.G., Freidig A.P., Delatour T., Scholz G., Schilter B., van Bladeren P.J., Rietjens I.M.C.M. Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared to male rats. Toxicol. Sci. 2009, 110(2):255-269.
27. 32PPostlabelling 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.
28. Renwick A.G., Walton K. The use of surrogate endpoints to assess potential toxicity in humans. Toxicol. Lett. 2001, 120(1-3):97-110.
29. Rietjens, I.M.C.M., Punt, A., Schilter, B., Scholz, G., Delatour, T., Van Bladeren, P.J., 2010. In-silico methods for physiologically based biokinetics (PBBK) models describing bioactivation and detoxification of coumarin and estragole; implication for risk assessment. Mol. Nutr. Food Res. 54 (2), 195-207.
30. Sander M., Cadet J., Casciano D.A., Galloway S.M., Marnett L.J., Novak R.F., Pettit S.D., Preston R.J., Skare J.A., Williams G.M., Van Houten B., Gollapudi B.B. Proceedings of a workshop on DNA adducts: biological significance and applications to risk assessment Washington, DC, April 13-14, 2004. Toxicol. Appl. Pharmacol. 2005, 208:1-20.
31. SCF (Scientific Committee on Food) (2001), Opinion of the scientific committee on food on estragole (1-allyl-4-methoxybenzene), http://ec.europa.eu/food/fs/sc/scf/out104_en.pdf.
32. Shuker D.E.G., Farmer P.B. Relevance of urinary DNA adducts as markers of carcinogen exposure. Chem. Res. Toxicol. 1992, 5(4):450-460.
33. Sidhu J.S., Farin F.M., Omiecinski C.J. Influence of extracellular matrix overlay on Phenobarbital-mediated induction of CYP 2B1, 2B2 and 3A1 genes in primary adult rat hepatocyte culture. Arch. Biochem. Biophys. 1993, 301:103-113.
34. 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.
35. Williams G.M. Application of mode-of-action consideration in human cancer risk assessment. Toxicol. Lett. 2008, 180:75-80.
36. Wiseman R.W., Fennell T.R., Miller J.A., Miller E.C. Further characterization of the DNA adducts formed by electrophilic esters of the hepatocarcinogens 1′-hydroxysafrole and 1′-hydroxyestragole in vitro and in mouse liver in vivo, including new adducts at C-8 and N-7 of guanine residue. Cancer Res. 1985, 45:3096-3105.
37. 1mice. Cancer Res. 1987, 47:2275-2283.
38. Yang R.S.H., El-Masri H.A., Thomas R.S., Dobrev I., Dennison J.E., Bae D.S., Campain J.A., Liao K.H., Reisfeld B., Andersen M.E., Mumtaz M.M. Chemical mixture toxicology: from descriptive to mechanistic and going on to in silico toxicology. Environ. Toxicol. Pharmacol. 2004, 18:65-81.
39. Young J.F., Luecke R.H., Doerge D.R. Physiologically based pharmacokinetic/pharmacodynamic model for acrylamide and its metabolites in mice, rats, and humans. Chem. Res. Toxicol. 2007, 20:388-399.