Heterogenous effects of anthraquinones on drug-metabolizing enzymes in the liver and small intestine of rat

Chemico-Biological Interactions

Volumn 126, Issue 1, 2000, Pages 63-77

  Longo, Vincenzo ^a   Amato, Giada ^a   Salvetti, Alessandra ^a   Gervasi, Pier Giovanni ^a  

^a Ist Mutagenesi Differenziamento C   (Italy)

Author keywords

Anthraquinones; Cytochrome P450; DT diaphorase enzymes; GST; UDP GT

Indexed keywords

ANTHRAQUINONE DERIVATIVE; DRUG METABOLIZING ENZYME; ETHOXYRESORUFIN DEETHYLASE; PHENACETIN O DEETHYLASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); UNSPECIFIC MONOOXYGENASE;

ANIMAL EXPERIMENT; ARTICLE; CARCINOGENESIS; CONTROLLED STUDY; ENZYME INDUCTION; ENZYME INHIBITION; IMMUNOBLOTTING; KIDNEY MICROSOME; LIVER MICROSOME METABOLISM; MALE; NONHUMAN; NORTHERN BLOTTING; RAT;

ANIMALS; ANTHRAQUINONES; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP1A2; GLUCURONOSYLTRANSFERASE; GLUTATHIONE TRANSFERASE; IMMUNOBLOTTING; INTESTINE, SMALL; LIVER; MALE; NAD(P)H DEHYDROGENASE (QUINONE); RATS; RATS, SPRAGUE-DAWLEY; RNA, MESSENGER;

EID: 0034647113     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(00)00154-X     Document Type: Article

References (49)

1. Brown J.P. A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds. Mutat. Res. 75:1980;243-277.
2. Sendelback L.E. A review of the toxicity and carcinogenicity of anthraquinone derivatives. Toxicology. 57:1989;227-240.
3. Brown J.P., Dietrich P.S. Mutagenicity of anthraquinone and benzanthrone derivatives in the Salmonella/microsome test: activation of anthraquinone glycosides by enzymic extracts of rat cecal bacteria. Mutat. Res. 66:1979;9-24.
4. Westendorf J., Marquardt H., Poginsky B., Dominiak M., Schmidt J., Marquardt H. Genotoxicity of naturally occurring hydroxyanthraquinones. Mutat. Res. 240:1990;1-12.
5. Mueller S.O., Lutz W.K., Stopper H. Factors affecting the genotoxicity, potency ranking of natural anthraquinones in mammalian cell culture systems. Mutat. Res. 414:1998;125-129.
6. Lewis D.F.V., Lake B.G. Molecular modelling of cyp 1A subfamily members based on an alignement with cyp 102: rationalization of cyp 1A substrate specificity in terms of active site amino acide residues. Xenobiotica. 26:1996;723-753.
7. Ayrton A.D., Lewis D.F.V., Ioannides C., Walker R. Anthraflavic is a potent and specific inhibitor of cytochrome P448 activity. Biochim. Biophys. Acta. 916:1987;328-331.
8. Simi S., Morelli S., Gervasi P.G., Rainaldi G. Clastogenicity of anthraquinones in V79 and in three derived cell lines expressing P450 enzymes. Mutat. Res. 347:1995;151-156.
9. Fratta D., Simi S., Rainaldi G., Gervasi P.G. Role of cytochrome P450 isoenzymes in the bioactivation of hydroxyanthraquinones. Anticancer Res. 14:1994;2597-2604.
10. Dahms M., Lotz R., Lang W., Renner V., Bayer E., Spahn-Langguth H. Elucidation of phase I and phase II metabolic pathways of rhein: species differences and their potential relevance. Drug Metab. Dispos. 25:1997;442-452.
11. Mueller S.O., Stopper H., Dekant W. Biotransformation of the anthraquinones emodin and chrysophanol by cytochrome P450 enzymes. Drug Metab. Dispos. 26:1998;540-546.
12. Mori H., Yoshimi N., Iwata H., Mori Y., Hara A., Tanaka T., Kawai K. Carcinogenicity of naturally occuring 1-hydroxyanthraquinone in rats: induction of large bowel, liver and stomach neoplasms. Carcinogenesis. 11:1990;799-802.
13. Siegers C.R. Anthrenoid laxatives and colorectal cancer. TIPS. 13:1992;229-231.
14. Fasco M.J., Silkworth J.B., Dumbar D.A., Harrison G.G., Kaminky L.S. Rat small intestinal cytochrome P450 probed by warfarin metabolism. Mol. Pharmacol. 43:1993;226-233.
15. Gonzalez F.J., Gelboin H.V. Role of human cytochrome P450 in the metabolic activation of chemical carcinogenesis and toxins. Drug Metab. Rev. 26:1994;165-183.
16. Ioannides C., Ayrton A.D., Lewis D.F.V., Walker R. Extrapolation of in vitro antimutagicity to the in vivo situation: the case for anthraflavic acid. Bronzetti G., Hayatsu H., De Flora S., Waters M.D., Shankel D.M. Antimutagenesis and Anticarcinogenesis Mechanism III. 1993;103-110 Plenum Press, New York and London.
17. Ayrton A.D., Ioannides C., Walker R. Induction of rat hepatic cytochrome P-450 I proteins by the antimutagen anthraflavic acid. Food Chem. Toxicol. 26:1988;909-915.
18. Chaloupka K., Santostefano M., Golfarb H.S., Lin G., Myers M.J., Tsyrolv I.B., Gelboin H.V., Krishman V., Safe S. Aryl hydrocarbon (Ah) receptor-independent induction of Cyp1a2 gene expression by acenaphthylene and related compounds in C57BL/6 mice. Carcinogenesis. 15:1994;2835-2840.
19. Nebert D.W., Petersen D.D., Fornace A.J. Cellular responses to oxidative stress: the [Ah] gene battery as a paradigm. Environ. Health Pers. 88:1990;13-25.
20. Longo V., Citti L., Gervasi P.G. Metabolism of diethylnitrosamine by nasal mucosa and hepatic microsomes from hamster and rat: species specificity of nasal mucosa. Carcinogenesis. 7:1986;1323-1328.
21. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193:1951;265-275.
22. Omura T., Sato R. The carbon-monoxide binding protein of liver microsomes. I. Evidences for its hemoprotein nature. J. Biol. Chem. 293:1964;2370-2378.
23. Ko I.Y., Park S.S., Song B.J., Patten C., Tan Y., Han J.C., Yang C.S., Gelboin H.V. Monoclonal antibodies to ethanol-induced rat liver cytochrome P450 that metabolize aniline and nitrosamines. Cancer Res. 47:1987;3101-3109.
24. Tu Y.Y., Yang C.S. High-affinity nitrosamine dealkylase system in rat liver microsomes and its induction by fasting. Cancer Res. 43:1983;623-629.
25. Krijgsheld K.R., Gram T.E. Selective induction of renal microsomal cytochrome P450-linked monooxygenases by 1,1-dichloroethylene in mice. Biochem. Pharmacol. 33:1984;1951-1956.
26. Aitio A. A single sensitive assay of ethoxycoumarin deethylation. Anal. Biochem. 85:1978;488-491.
27. Longo V., Mazzaccaro A., Naldi F., Gervasi P.G. Drug metabolizing enzymes in liver olfactory and respiratory epithelium of cattle. J. Biochem. Toxicol. 6:1991;123-128.
28. Platt K.L., Molitor E., Dohemer J., Dogra S., Oesch F. Genetically engineered V79 Chinese hamster cell expression of purified cytochrome P450IIB1 monooxygenase activity. J. Biochem. Toxicol. 4:1989;1-6.
29. Wermuth B., Platt K.L., Scidel A., Oesch F. Carbonyl reductase provides the enzymatic basis of quinone detoxication in man. Biochem. Pharmacol. 35:1986;1277-1282.
30. Habig W.H., Pabst M.J., Jakoby W.B. Glutathione transferase, the first step in mercapturic acid formation. J. Biol. Chem. 249:1974;7140-7149.
31. Mackenzie P.I., Hanninen O. A sensitive kinetic assay for UDP glucuronosyl transferase using 1-naphthol as substrate. Anal. Biochem. 109:1980;362-368.
32. Laemmli U.K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 227:1970;680-685.
33. Towbin H., Stachelin P., Gordon J. Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications. Proc. Natl. Acad. Sci. USA. 76:1979;4350-4354.
34. Amato G., Longo V., Mazzaccaro A., Gervasi P.G. Microsomal oxidation of N,N diethylformamide and its effect on P450-dependent monooxygenases in rat liver. Chem. Res. Toxicol. 9:1996;882-890.
35. Chomczynski P., Sacchi N. Single step of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction. Anal. Biochem. 162:1987;156-159.
36. Sambrook J., Fritsch E.F., Maniatis T. Electrophoresis of RNA through gels containing formaldehyde. Ford N., Nolan C., Ferguson M. Molecular Cloning a Laboratory Manual. 1:1989;7.43-7.48 Cold Spring Harbor Laboratory Press, New York.
37. Funae Y., Ymaoke S. Cytochrome P450 in rodents. Shenkman J.B., Helmut G. Cytochrome P450. 1993;221-238 Spring-Verlag, Berlin.
38. Tsyrlov I.B., Goldfarb I.S., Gelboin H.V. Enzyme-kinetic and immunochemical characteristics of mouse cDNA-expressed, microsomal and purified CYP1A1 and CYP1A2. Arch. Biochem. Biophys. 307:1993;259-266.
39. Lubet R.A., Mayer R.T., Cameron J.W., Nims R.W., Burke M.D., Wolf T., Guengerich F.P. Dealkylation of pentoxyresorufin: a rapid and sensitive assay for measuring induction of cytochrome(s) P450 by phenobarbital and other xenobiotic in rat. Arch. Biochem. Biophys. 238:1985;43-48.
40. Reinke L.A., Sexter S.H., Rikans L.E. Comparison of ethanol and imidazole pretreatments on hepatic monooxygenase activities in the rat. Res. Commun. Chem. Pathol. Pharmacol. 47:1985;97-106.
41. Arlotto M.P., Sonderfan A.J., Klassen C.D., Parkinson A. Studies on the pregnenolone-16α-carbonitrile-inducible of rat liver microsomal cytochrome P450 and UDP-glucuronyltransferase. Biochem. Pharmacol. 36:1987;3859-3866.
42. Gonzalez F. The molecular biology of cytochrome P450s. Pharmacol. Rev. 41:1989;91-92.
43. Thomas P.E., Reik L.M., Ryan D.E., Levin W. Induction of two immunochemically related rat liver cytochrome P450 isozymes, cytochrome P450c and cytochrome P450d, by structurally diverse xenobiotics. J. Biol. Chem. 258:1982;4590-4598.
44. Lilienblum W., Walli A.K., Bock K.W. Differential induction of rat liver microsomal UDP-glucuronosyltransferase activities by various inducing agents. Biochem. Pharmacol. 31:1982;907-913.
45. Silver G., Reid L.M., Kranter K.S. DEX-mediated regulation of 3-MC induced cytochrome P450d mRNA accumulation in primary rat hepatocytes. J. Biol. Chem. 265:1990;3134-3138.
46. Kuzuya M., Noguchi A., Kawai K., Mori H. Quantum chemical study for genotoxic and antitumor activities of hydroxyanthraquinones. Regul. Toxicol. Pharm. 13:1991;185-194.
47. Stresser D.M., Kupfer D. Catalytic characteristics of CYP3A4: requirement for a phenolic function in ortho hydroxylation of estradiol and mono-O-demethylated methoxychlor. Biochemistry. 36:1997;2203-2210.
48. Breimer D.D., Baars A.J. Pharmacokinetics and metabolism of anthraquinone laxatives. Pharmacology. 14:1976;30-47.
49. de Vitte P. Metabolism and pharmacokinetics of anthranoids. Pharmacology. 47:1993;86-97.