Dose-dependent DNA adduct formation by cinnamaldehyde and other food-borne α,β-unsaturated aldehydes predicted by physiologically based in silico modelling

Toxicology in Vitro

Volumn 31, Issue , 2016, Pages 114-125

  Kiwamoto, R ^a   Ploeg, D ^a   Rietjens, I M C M ^a   Punt, A ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Cinnamaldehyde; DNA adducts; Genotoxicity; Physiologically based kinetic dynamic modelling; Read across; , Unsaturated aldehydes

Indexed keywords

ALCOHOL DEHYDROGENASE; ALDEHYDE DEHYDROGENASE; ALDEHYDE DERIVATIVE; ALDEHYDE REDUCTASE; ALPHA,BETA UNSATURATED ALDEHYDE; CINNAMALDEHYDE; CINNAMIC ACID; CINNAMYL ALCOHOL; GLUTATHIONE TRANSFERASE; UNCLASSIFIED DRUG; ALDEHYDE; DNA ADDUCT; FLAVORING AGENT; GLUTATHIONE; MUTAGENIC AGENT;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; COMPUTER MODEL; DNA ADDUCT; FEMALE; GENOTOXICITY; HUMAN; HUMAN TISSUE; IN VIVO STUDY; MALE; NONHUMAN; NORMAL HUMAN; OXIDATION; PHYSIOLOGICALLY BASED KINETIC DYNAMIC MODEL; RAT; RISK FACTOR; ANIMAL; BIOLOGICAL MODEL; COMPUTER SIMULATION; DIET; LIVER; METABOLISM; SMALL INTESTINE; SPRAGUE DAWLEY RAT;

ALCOHOL DEHYDROGENASE; ALDEHYDE DEHYDROGENASE; ALDEHYDE REDUCTASE; ALDEHYDES; ANIMALS; COMPUTER SIMULATION; DIET; DNA ADDUCTS; FEMALE; FLAVORING AGENTS; GLUTATHIONE; GLUTATHIONE TRANSFERASE; HUMANS; INTESTINE, SMALL; LIVER; MALE; MODELS, BIOLOGICAL; MUTAGENS; RATS, SPRAGUE-DAWLEY;

EID: 84949257466     PISSN: 08872333     EISSN: 18793177     Source Type: Journal    
DOI: 10.1016/j.tiv.2015.11.014     Document Type: Article

References (46)

1. Adams T.B., Cohen S.M., Doull J., Feron V.J., Goodman J.I., Marnett L.J., Munro I.C., Portoghese P.S., Smith R.L., Waddell W.J., Wagner B.M. The FEMA GRAS assessment of cinnamyl derivatives used as flavor ingredients. Food Chem. Toxicol. 2004, 42:157-185.
2. Adams T.B., Gavin C.L., Taylor S.V., Waddell W.J., Cohen S.M., Feron V.J., Goodman J., Rietjens I.M.C.M., Marnett L.J., Portoghese P.S., Smith R.L. The FEMA GRAS assessment of alpha,beta-unsaturated aldehydes and related substances used as flavor ingredients. Food Chem. Toxicol. 2008, 46:2935-2967.
3. Assimakopoulos S.F., Thomopoulos K.C., Patsoukis N., Georgiou C.D., Scopa C.D., Nikolopoulou V.N., Vagianos C.E. Evidence for intestinal oxidative stress in patients with obstructive jaundice. Eur. J. Clin. Investig. 2006, 36:181-187.
4. Blakemore W.M., Thompson H.C. Trace analysis of cinnamaldehyde in animal feed, human-urine, and wastewater by electron-capture gas-chromatography. J. Agric. Food Chem. 1983, 31:1047-1052.
5. Boyland E., Chasseau L.F. Enzymes catalysing conjugations of glutathione with alpha, beta-unsaturated carbonyl compounds. Biochem. J. 1968, 109. (651-661).
6. Brown R.P., Delp M.D., Lindstedt S.L., Rhomberg L.R., Beliles R.P. Physiological parameter values for physiologically based pharmacokinetic models. Toxicol. Ind. Health 1997, 13:407-484.
7. Canonero R., Martelli A., Marinari U.M., Brambilla G. Mutation induction in Chinese hamster lung V79 cells by five alk-2-enals produced by lipid peroxidation. Mutat. Res. 1990, 244:153-156.
8. Chaudhary A.K., Nokubo M., Reddy G.R., Yeola S.N., Morrow J.D., Blair I.A., Marnett L.J. Detection of endogenous malondialdehyde-deoxyguanosine adducts in human liver. Science 1994, 265:1580-1582.
9. Cocchiara J., Letizia C.S., Lalko J., Lapczynski A., Api A.M. Fragrance material review on cinnamaldehyde. Food Chem. Toxicol. 2005, 43:867-923.
10. Csanady G.A., Filser J.G. A physiological toxicokinetic model for inhaled propylene oxide in rat and human with special emphasis on the nose. Toxicol. Sci. 2007, 95:37-62.
11. DeJongh J., Verhaar H.J., Hermens J.L. A quantitative property-property relationship (QPPR) approach to estimate in vitro tissue-blood partition coefficients of organic chemicals in rats and humans. Arch. Toxicol. 1997, 72:17-25.
12. Delbressine L.P., Klippert P.J., Reuvers J.T., Seuttler-Berlage F. Isolation and identification of mercapturic acids of cinnamic aldehyde and cinnamyl alcohol from urine of female rats. Arch. Toxicol. 1981, 49:57-64.
13. EFSA Minutes of the 26th Plenary Meeting of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact With Food 2007, http://www.efsa.europa.eu/en/events/event/afc071127-m.pdf.
14. EFSA Genotoxicity Test Strategy for Substances Belonging to Subgroups of FGE.191: Statement of the Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) 2008, http://www.efsa.europa.eu/en/scdocs/doc/854.pdf.
15. EFSA Flavouring Group Evaluation 214: alpha,beta-unsaturated aldehydes and precursors from chemical subgroup 3.1 of FGE.19: cinnamyl derivatives. Scientific Opinion of the Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) 2009, (http://www.efsa.europa.eu/en/scdocs/doc/880.pdf).
16. EFSA Flavouring Group Evaluation 214: alpha,beta-unsaturated aldehydes and precursors from chemical subgroup 3.1 of FGE.19: cinnamyl derivatives. Scientific Opinion of the Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) 2009, (http://www.efsa.europa.eu/sites/default/files/scientific_output/files/main_documents/880.pdf).
17. Eisenbrand G., Schuhmacher J., Golzer P. The influence of glutathione and detoxifying enzymes on DNA damage induced by 2-alkenals in primary rat hepatocytes and human lymphoblastoid cells. Chem. Res. Toxicol. 1995, 8:40-46.
18. Frederick C.B., Potter D.W., Chang-Mateu M.I., Andersen M.E. A physiologically based pharmacokinetic and pharmacodynamic model to describe the oral dosing of rats with ethyl acrylate and its implications for risk assessment. Toxicol. Appl. Pharmacol. 1992, 114:246-260.
19. 2-(1,3-propano)-2'-deoxyguanosine adducts in mammalian cells. Chem. Res. Toxicol. 1996, 9:1207-1213.
20. Janzowski C., Glaab V., Mueller C., Straesser U., Kamp H.G., Eisenbrand G. Alpha,beta-unsaturated carbonyl compounds: induction of oxidative DNA damage in mammalian cells. Mutagenesis 2003, 18:465-470.
21. JECFA Evaluation of Certain Food Additives and Contaminants: Fifty-fifth Report of the Joint FAO/WHO Expert Committee on Food Additives 2001, http://whqlibdoc.who.int/trs/WHO_TRS_901.pdf.
22. JECFA Evaluation of Certain Food Additives and Contaminants: Sixty-first Report of the Joint FAO/WHO Expert Committee on Food Additives 2004, http://whqlibdoc.who.int/trs/WHO_TRS_922.pdf.
23. JECFA Evaluation of Certain Food Additives: Sixty-third Report of the Joint FAO/WHO Expert Committee on Food Additives 2005, http://whqlibdoc.who.int/trs/WHO_TRs_928.pdf.
24. Johanson G., Filser J.G. A physiologically based pharmacokinetic model for butadiene and its metabolite butadiene monoxide in rat and mouse and its significance for risk extrapolation. Arch. Toxicol. 1993, 67:151-163.
25. Kirman C.R., Gargas M.L., Deskin R., Tonner-Navarro L., Andersen M.E. A physiologically based pharmacokinetic model for acrylamide and its metabolite, glycidamide, in the rat. J. Toxicol. Environ. Health A 2003, 66:253-274.
26. Kiwamoto R., Rietjens I.M.C.M., Punt A. A physiologically based in silico model for trans-2-hexenal detoxification and DNA adduct formation in rat. Chem. Res. Toxicol. 2012, 25:2630-2641.
27. Kiwamoto R., Spenkelink A., Rietjens I.M.C.M., Punt A. A physiologically based in silico model for trans-2-hexenal detoxification and DNA adduct formation in human including interindividual variation indicates efficient detoxification and a negligible genotoxicity risk. Arch. Toxicol. 2013, 87(9):1725-1737.
28. Kiwamoto R., Spenkelink A., Rietjens I.M.C.M., Punt A. An integrated QSAR-PBK/D modelling approach for predicting detoxification and DNA adduct formation of 18 acyclic food-borne alpha,beta-unsaturated aldehydes. Toxicol. Appl. Pharmacol. 2015, 282:108-117.
29. 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc. Natl. Acad. Sci. U. S. A. 1994, 91:7491-7495.
30. NTP NTP Technical Report on the Toxicology and Carcinogenesis Studies of trans-Cinnamaldehyde (Microencapsulated) (CAS No. 14371-10-9) in F344/N Rats and B6C3F1 Mice (Feed Studies) 2004, http://ntp.niehs.nih.gov/ntp/htdocs/lt_rpts/tr514.pdf.
31. Peters M.M., Caldwell J. Studies on trans-cinnamaldehyde. 1. The influence of dose size and sex on its disposition in the rat and mouse. Food Chem. Toxicol. 1994, 32:869-876.
32. Pietruszko R., Crawford K., Lester D. Comparison of substrate specificity of alcohol dehydrogenases from human liver, horse liver, and yeast towards saturated and 2-enoic alcohols and aldehydes. Arch. Biochem. Biophys. 1973, 159:50-60.
33. Potter D.W., Tran T.B. Rates of ethyl acrylate binding to glutathione and protein. Toxicol. Lett. 1992, 62:275-285.
34. Potter D.W., Tran T.B. Apparent rates of glutathione turnover in rat tissues. Toxicol. Appl. Pharmacol. 1993, 120:186-192.
35. 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 with male rats. Toxicol. Sci. 2009, 110:255-269.
36. 2-deoxyguanosine adducts of cinnamaldehyde. A stereocontrolled route to deoxyguanosine adducts of α,β-unsaturated aldehydes. Tetrahedron Lett. 2003, 44:7513-7516.
37. 14C-labelled cinnamic aldehyde following single and multiple oral administration in male Fischer 344 rats. Food Chem. Toxicol. 1993, 31:253-261.
38. 32P-post-labeling technique. Carcinogenesis 1999, 20:1345-1350.
39. 2-propanodeoxyguanosine adducts of 2-hexenal in vivo. Chem. Res. Toxicol. 1999, 12:335-340.
40. 2-propanodeoxyguanosine in DNA. Chem. Res. Toxicol. 2006, 19:563-570.
41. Sweeney L.M., Kirman C.R., Gargas M.L., Carson M.L., Tardiff R.G. Development of a physiologically-based toxicokinetic model of acrylamide and glycidamide in rats and humans. Food Chem. Toxicol. 2010, 48:668-685.
42. van de Kerkhof E.G., de Graaf I.A., Groothuis G.M. In vitro methods to study intestinal drug metabolism. Curr. Drug Metab. 2007, 8:658-675.
43. Witz G. Biological interactions of alpha,beta-unsaturated aldehydes. Free Radic. Biol. Med. 1989, 7:333-349.
44. Yuan J.H., Dieter M.P., Bucher J.R., Jameson C.W. Toxicokinetics of cinnamaldehyde in F344 rats. Food Chem. Toxicol. 1992, 30:997-1004.
45. Yuan J., Bucher J.R., Goehl T.J., Dieter M.P., Jameson C.W. Quantitation of cinnamaldehyde and cinnamic acid in blood by HPLC. J. Anal. Toxicol. 1992, 16:359-362.
46. Zhao H., Xie Y.H., Yang Q., Cao Y., Tu H.H., Cao W., Wang S.W. Pharmacokinetic study of cinnamaldehyde in rats by GC-MS after oral and intravenous administration. J. Pharm. Biomed. 2014, 89:150-157.