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Volumn 127, Issue 2, 2000, Pages 109-124

Evidence for cytochrome P4501A2-mediated protein covalent binding of thiabendazole and for its passive intestinal transport: Use of human and rabbit derived cells

Author keywords

Covalent binding; Cytochrome P450; In vitro models; Intestinal transport; Thiabendazole

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; BETA NAPHTHOFLAVONE; CLOFIBRATE; FUNGICIDE; PHENACETIN O DEETHYLASE; PHENOBARBITAL; RIFAMPICIN; TIABENDAZOLE;

EID: 0034600763     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(00)00167-8     Document Type: Article
Times cited : (19)

References (39)
  • 1
    • 0001358504 scopus 로고
    • Antiparasitic drugs. IV. 2-(4′-thiazolyl)benzimidazole, a new anthelminthic
    • Brown H.D., Matzuk A.R., Ilves I.R.K. et al. Antiparasitic drugs. IV. 2-(4′-thiazolyl)benzimidazole, a new anthelminthic. J. Am. Soc. 83:1961;1764.
    • (1961) J. Am. Soc. , vol.83 , pp. 1764
    • Brown, H.D.1    Matzuk, A.R.2    Ilves, I.R.K.3
  • 2
    • 17744408074 scopus 로고
    • Thiabendazole for the treatment of trichinosis in humans
    • Hennekeuser H.H., Pabst K., Poeplau W., Gerok W. Thiabendazole for the treatment of trichinosis in humans. Texas Rep. Biol. Med. 27(Suppl. 2):1969;581-596.
    • (1969) Texas Rep. Biol. Med. , vol.27 , Issue.2 SUPPL. , pp. 581-596
    • Hennekeuser, H.H.1    Pabst, K.2    Poeplau, W.3    Gerok, W.4
  • 3
    • 0027133996 scopus 로고
    • Persistence and efficacy of thiabendazole on potatoes for control of silver scurf
    • Szeto S.Y., Joshi V., Price P.M., Holley J. Persistence and efficacy of thiabendazole on potatoes for control of silver scurf. J. Agric. Food Chem. 41:1993;2156-2159.
    • (1993) J. Agric. Food Chem. , vol.41 , pp. 2156-2159
    • Szeto, S.Y.1    Joshi, V.2    Price, P.M.3    Holley, J.4
  • 4
    • 0028438671 scopus 로고
    • Liquid chromatographic fluorescence method for the determination of thiabendazole residues in green bananas and banana pulp
    • Arenas R.V., Johnson N.A. Liquid chromatographic fluorescence method for the determination of thiabendazole residues in green bananas and banana pulp. J. AOAC Int. 77:1994;710-713.
    • (1994) J. AOAC Int. , vol.77 , pp. 710-713
    • Arenas, R.V.1    Johnson, N.A.2
  • 6
    • 0025308251 scopus 로고
    • Nephrotoxicity of thiabendazole in mice depleted of glutathione by treatment with DL-buthionine sulphoximine
    • Mizutani T., Ito K., Nomura H., Nakanishi K. Nephrotoxicity of thiabendazole in mice depleted of glutathione by treatment with DL-buthionine sulphoximine. Food Chem. Toxicol. 28:1990;169-177.
    • (1990) Food Chem. Toxicol. , vol.28 , pp. 169-177
    • Mizutani, T.1    Ito, K.2    Nomura, H.3    Nakanishi, K.4
  • 7
    • 0026605312 scopus 로고
    • Nephrotoxicity of thiazoles structurally related to thiabendazole in mice depleted of glutathione by treatment with buthionine sulfoximine
    • Mizutani T., Yoshida K., Ito K. Nephrotoxicity of thiazoles structurally related to thiabendazole in mice depleted of glutathione by treatment with buthionine sulfoximine. Res. Commun. Chem. Pathol. Pharmacol. 75:1992;29-38.
    • (1992) Res. Commun. Chem. Pathol. Pharmacol. , vol.75 , pp. 29-38
    • Mizutani, T.1    Yoshida, K.2    Ito, K.3
  • 8
    • 0027537187 scopus 로고
    • Possible role of thioformamide as a proximate toxicant in the nephrotoxicity of thiabendazole and related thiazoles inglutathione-depleted mice: Structure-toxicity and metabolic studies
    • Mizutani T., Yoshida K., Kawazoe S. Possible role of thioformamide as a proximate toxicant in the nephrotoxicity of thiabendazole and related thiazoles inglutathione-depleted mice: structure-toxicity and metabolic studies. Chem. Res. Toxicol. 6:1993;174-179.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 174-179
    • Mizutani, T.1    Yoshida, K.2    Kawazoe, S.3
  • 9
    • 0022975730 scopus 로고
    • Irreversible in vivo and in vitro binding of thiabendazole to tissue proteins of pregnant mice
    • Yoneyama M., Ichikawa H. Irreversible in vivo and in vitro binding of thiabendazole to tissue proteins of pregnant mice. Food Chem. Toxicol. 24:1986;1283-1286.
    • (1986) Food Chem. Toxicol. , vol.24 , pp. 1283-1286
    • Yoneyama, M.1    Ichikawa, H.2
  • 10
    • 0020325715 scopus 로고
    • Metabolic activation and drug toxicity. I. Correlation of changes in covalent binding of reactivity metabolites with changes in the incidence and severity of toxicity
    • Nelson S.D. Metabolic activation and drug toxicity. I. Correlation of changes in covalent binding of reactivity metabolites with changes in the incidence and severity of toxicity. J. Med. Chem. 25:1982;753-765.
    • (1982) J. Med. Chem. , vol.25 , pp. 753-765
    • Nelson, S.D.1
  • 11
    • 0001001751 scopus 로고
    • The metabolic fate of thiabendazole in sheep
    • Tocco D.J. The metabolic fate of thiabendazole in sheep. J. Med. Chem. 7:1964;399-405.
    • (1964) J. Med. Chem. , vol.7 , pp. 399-405
    • Tocco, D.J.1
  • 12
    • 0001280223 scopus 로고
    • Absorption, metabolism and elimination of thiabendazole in farm animals and a method for its estimation in biological materials
    • Tocco D.J., Egerton J.R., Bowers W., Christensen V.W., Rosenblum C. Absorption, metabolism and elimination of thiabendazole in farm animals and a method for its estimation in biological materials. J. Pharmacol. Exp. Ther. 149:1965;263-271.
    • (1965) J. Pharmacol. Exp. Ther. , vol.149 , pp. 263-271
    • Tocco, D.J.1    Egerton, J.R.2    Bowers, W.3    Christensen, V.W.4    Rosenblum, C.5
  • 13
    • 0013923482 scopus 로고
    • Absorption, metabolism, and excretion of thiabendazole in man and laboratory animals
    • Tocco D.J., Rosenblum C., Martin C.M., Robinson H.J. Absorption, metabolism, and excretion of thiabendazole in man and laboratory animals. Toxicol. Appl. Pharmacol. 9:1966;31-39.
    • (1966) Toxicol. Appl. Pharmacol. , vol.9 , pp. 31-39
    • Tocco, D.J.1    Rosenblum, C.2    Martin, C.M.3    Robinson, H.J.4
  • 14
    • 0031968527 scopus 로고    scopus 로고
    • Identification of human and rabbit cytochromes P4501A2 as major isoforms involved in thiabendazole 5-hydroxylation
    • Coulet M., Dacasto M., Eeckhoutte C. et al. Identification of human and rabbit cytochromes P4501A2 as major isoforms involved in thiabendazole 5-hydroxylation. Fundam. Clin. Pharmacol. 12:1998;225-235.
    • (1998) Fundam. Clin. Pharmacol. , vol.12 , pp. 225-235
    • Coulet, M.1    Dacasto, M.2    Eeckhoutte, C.3
  • 15
    • 0001149618 scopus 로고    scopus 로고
    • Comparative metabolism of thiabendazole in cultured hepatocytes from rats, rabbits, calves, pigs and sheep, including the formation of protein-bound residues
    • Coulet M., Eeckhoutte C., Larrieu G. et al. Comparative metabolism of thiabendazole in cultured hepatocytes from rats, rabbits, calves, pigs and sheep, including the formation of protein-bound residues. J. Agric. Food Chem. 46:1998;742-748.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 742-748
    • Coulet, M.1    Eeckhoutte, C.2    Larrieu, G.3
  • 16
    • 0024593744 scopus 로고
    • Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability
    • Hidalgo J.J., Raub T.J., Borchardt R.T. Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability. Gastroenterology. 96:1989;736-749.
    • (1989) Gastroenterology , vol.96 , pp. 736-749
    • Hidalgo, J.J.1    Raub, T.J.2    Borchardt, R.T.3
  • 17
    • 0023571719 scopus 로고
    • Expression of five forms of microsomal cytochrome P450 in primary cultures of rabbit hepatocytes treated with various classes of inducers
    • Daujat M., Pichard L., Dalet C. Expression of five forms of microsomal cytochrome P450 in primary cultures of rabbit hepatocytes treated with various classes of inducers. Biochem. Pharmacol. 36:1987;3597-3606.
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 3597-3606
    • Daujat, M.1    Pichard, L.2    Dalet, C.3
  • 18
    • 0016174577 scopus 로고
    • Preparation and properties of partially purified cytochrome P450 and reduced nicotinamide adenine dinucleotide phosphatase cytochrome P450 reductase from rabbit liver microsomes
    • Van der Hoeven T., Coon M.J. Preparation and properties of partially purified cytochrome P450 and reduced nicotinamide adenine dinucleotide phosphatase cytochrome P450 reductase from rabbit liver microsomes. J. Biol. Chem. 249:1974;6202-6210.
    • (1974) J. Biol. Chem. , vol.249 , pp. 6202-6210
    • Van Der Hoeven, T.1    Coon, M.J.2
  • 19
    • 0022186670 scopus 로고
    • Measurement of protein using bicinchoninic acid
    • Smith P.K., Krohn R.I., Hermason G.T. Measurement of protein using bicinchoninic acid. Anal. Biochem. 150:1985;76-85.
    • (1985) Anal. Biochem. , vol.150 , pp. 76-85
    • Smith, P.K.1    Krohn, R.I.2    Hermason, G.T.3
  • 20
    • 0031284677 scopus 로고    scopus 로고
    • Aflatoxin B1-induced DNA adduct formation and p53 mutations in CYP450-expressing human liver cell lines
    • Macé K., Aguilar F., Wang J.S. Aflatoxin B1-induced DNA adduct formation and p53 mutations in CYP450-expressing human liver cell lines. Carcinogenesis. 18:1997;1291-1297.
    • (1997) Carcinogenesis , vol.18 , pp. 1291-1297
    • Macé, K.1    Aguilar, F.2    Wang, J.S.3
  • 21
    • 0032543382 scopus 로고    scopus 로고
    • Production of DNA strand breaks by N-nitrosodimethylamine and 2-amino-3-methylimidazo[4,5-f] quinoline in THLE cells expressing human CYP isoenzymes and inhibition by sulforaphane
    • Barcelo S., Macé K., Pfeifer A.M.A., Chipman J.K. Production of DNA strand breaks by N-nitrosodimethylamine and 2-amino-3-methylimidazo[4,5-f] quinoline in THLE cells expressing human CYP isoenzymes and inhibition by sulforaphane. Mutat. Res. 402:1998;111-120.
    • (1998) Mutat. Res. , vol.402 , pp. 111-120
    • Barcelo, S.1    Macé, K.2    Pfeifer, A.M.A.3    Chipman, J.K.4
  • 22
    • 0028171339 scopus 로고
    • Activation of promutagens in a human bronchial epithelial cell line stably expressing human cytochrome P450 1A2
    • Macé K., Gonzalez F.J., Mcconell I.R. Activation of promutagens in a human bronchial epithelial cell line stably expressing human cytochrome P450 1A2. Mol. Carcinogen. 11:1994;65-73.
    • (1994) Mol. Carcinogen. , vol.11 , pp. 65-73
    • Macé, K.1    Gonzalez, F.J.2    McConell, I.R.3
  • 23
    • 0002352192 scopus 로고
    • Highly efficient establisment of immortalized cells from adult human liver
    • Pfeifer A.M.A., Macé K., Tromvoukis Y., Lipsky M.M. Highly efficient establisment of immortalized cells from adult human liver. Meth. Cell Science. 17:1995;83-89.
    • (1995) Meth. Cell Science , vol.17 , pp. 83-89
    • Pfeifer, A.M.A.1    Macé, K.2    Tromvoukis, Y.3    Lipsky, M.M.4
  • 24
    • 0022357460 scopus 로고
    • A serum-free method for culturing normal human bronchial epithelial cells at clonal density
    • Lechner J.F., La Veck M.A. A serum-free method for culturing normal human bronchial epithelial cells at clonal density. J. Tissue Cult. Meth. 9:1985;43-48.
    • (1985) J. Tissue Cult. Meth. , vol.9 , pp. 43-48
    • Lechner, J.F.1    La Veck, M.A.2
  • 25
    • 0028242097 scopus 로고
    • Established cell lines for safety assessment of food contaminants: Differing furazolidone toxicity to V79, Hep 2 and Caco-2 cells
    • De Angelis I., Hoogenboom L.A.P., Huveneers-Oorsprong M.B.M., Zucco F., Stammati A. Established cell lines for safety assessment of food contaminants: differing furazolidone toxicity to V79, Hep 2 and Caco-2 cells. Food Chem. Toxicol. 32:1994;481-488.
    • (1994) Food Chem. Toxicol. , vol.32 , pp. 481-488
    • De Angelis, I.1    Hoogenboom, L.A.P.2    Huveneers-Oorsprong, M.B.M.3    Zucco, F.4    Stammati, A.5
  • 26
    • 0025856775 scopus 로고
    • The use of pig hepatocytes to study the nature of protein bound metabolites of furazolidone: A new analytical method for their detection
    • Hoogenboom L.A.P., Van Kammen M., Berghmans M.C.J., Koeman J.H., Kuiper H.A. The use of pig hepatocytes to study the nature of protein bound metabolites of furazolidone: a new analytical method for their detection. Food Chem. Toxicol. 28:1991;321-328.
    • (1991) Food Chem. Toxicol. , vol.28 , pp. 321-328
    • Hoogenboom, L.A.P.1    Van Kammen, M.2    Berghmans, M.C.J.3    Koeman, J.H.4    Kuiper, H.A.5
  • 27
    • 0026637031 scopus 로고
    • Epithelial cells in culture as a model for the intestinal transport of antimicrobial agents
    • Ranaldi G., Islam K., Sambuy Y. Epithelial cells in culture as a model for the intestinal transport of antimicrobial agents. Antimicrob. Ag. Chemother. 36:1992;1374-1381.
    • (1992) Antimicrob. Ag. Chemother. , vol.36 , pp. 1374-1381
    • Ranaldi, G.1    Islam, K.2    Sambuy, Y.3
  • 29
    • 0029680198 scopus 로고    scopus 로고
    • Major involvement of rabbit liver cytochrome P4501A in thiabendazole 5-hydroxylation
    • Rey-Grobellet X., Eeckhoutte C., Sutra J.F., Alvinerie M., Galtier P. Major involvement of rabbit liver cytochrome P4501A in thiabendazole 5-hydroxylation. Xenobiotica. 26:1996;765-778.
    • (1996) Xenobiotica , vol.26 , pp. 765-778
    • Rey-Grobellet, X.1    Eeckhoutte, C.2    Sutra, J.F.3    Alvinerie, M.4    Galtier, P.5
  • 30
    • 0014757218 scopus 로고
    • Carcinogenesis by chemicals: An overview
    • Miller J.A. Carcinogenesis by chemicals: An overview. Cancer Res. 30:1970;559-576.
    • (1970) Cancer Res. , vol.30 , pp. 559-576
    • Miller, J.A.1
  • 31
    • 0024315987 scopus 로고
    • Selective acetaminophen metabolite binding to hepatic and extrahepatic proteins: An in vivo and in vitro analysis
    • Bartolone J.B., Beierschmitt W.P., Birge R.B. et al. Selective acetaminophen metabolite binding to hepatic and extrahepatic proteins: an in vivo and in vitro analysis. Toxicol. Appl. Pharmacol. 99:1989;240-249.
    • (1989) Toxicol. Appl. Pharmacol. , vol.99 , pp. 240-249
    • Bartolone, J.B.1    Beierschmitt, W.P.2    Birge, R.B.3
  • 33
    • 0024348230 scopus 로고
    • Micronodular cirrhosis after thiabendazole
    • Roy M.A., Nugent F.W., Aretz H.T. Micronodular cirrhosis after thiabendazole. Dig. Dis. Sci. 34:1989;938-941.
    • (1989) Dig. Dis. Sci. , vol.34 , pp. 938-941
    • Roy, M.A.1    Nugent, F.W.2    Aretz, H.T.3
  • 34
    • 0029906811 scopus 로고    scopus 로고
    • Nephrotoxicity of thioformamide, a proximate toxicant of nephrotoxic thiazoles, in mice depleted of glutathione
    • Mizutani T., Suzuki K., Murakami M., Yoshida K., Nakanishi K. Nephrotoxicity of thioformamide, a proximate toxicant of nephrotoxic thiazoles, in mice depleted of glutathione. Res. Commun. Mol. Pathol. Pharmacol. 94:1996;89-101.
    • (1996) Res. Commun. Mol. Pathol. Pharmacol. , vol.94 , pp. 89-101
    • Mizutani, T.1    Suzuki, K.2    Murakami, M.3    Yoshida, K.4    Nakanishi, K.5
  • 35
    • 0002085981 scopus 로고
    • Benzimidazole anthelmintics and related compounds: Toxicity and evaluation of residues
    • A.G. Rico. New York: Academic Press
    • Delatour P., Parish R. Benzimidazole anthelmintics and related compounds: toxicity and evaluation of residues. Rico A.G. Drug Residues in Animals. 1986;175-203 Academic Press, New York.
    • (1986) Drug Residues in Animals , pp. 175-203
    • Delatour, P.1    Parish, R.2
  • 36
    • 0026981085 scopus 로고
    • Regulation of cytochrome P450 1A1 gene expression in a human intestinal cell line Caco-2
    • Boulenc X., Bourrie M., Fabre I. Regulation of cytochrome P450 1A1 gene expression in a human intestinal cell line Caco-2. J. Pharmacol. Exper. Therap. 263:1992;1471-1478.
    • (1992) J. Pharmacol. Exper. Therap. , vol.263 , pp. 1471-1478
    • Boulenc, X.1    Bourrie, M.2    Fabre, I.3
  • 37
    • 0028110184 scopus 로고
    • Expression of cytochrome P450 3A in HT29-MTX cells and Caco-2 clone TC7
    • Carrière V., Lesuffleur T., Barbat A. Expression of cytochrome P450 3A in HT29-MTX cells and Caco-2 clone TC7. FEBS Lett. 355:1994;247-250.
    • (1994) FEBS Lett. , vol.355 , pp. 247-250
    • Carrière, V.1    Lesuffleur, T.2    Barbat, A.3
  • 38
    • 0029998275 scopus 로고    scopus 로고
    • Comparative studies of drug-metabolizing enzymes in dog, monkey, and human small intestines, and in Caco-2 cells
    • Prueksaritanont T., Gorham L.M., Hochman J.H., Tran L.O., Vyas K.P. Comparative studies of drug-metabolizing enzymes in dog, monkey, and human small intestines, and in Caco-2 cells. Drug Metab. Dispos. 24:1996;634-642.
    • (1996) Drug Metab. Dispos. , vol.24 , pp. 634-642
    • Prueksaritanont, T.1    Gorham, L.M.2    Hochman, J.H.3    Tran, L.O.4    Vyas, K.P.5
  • 39
    • 0030465760 scopus 로고    scopus 로고
    • Development of Caco-2 cells expressing high levels of cDNA-derived cytochrome P450 3A4
    • Crespi C.L., Penman B.W., Hu M. Development of Caco-2 cells expressing high levels of cDNA-derived cytochrome P450 3A4. Pharm. Res. 13:1996;1635-1641.
    • (1996) Pharm. Res. , vol.13 , pp. 1635-1641
    • Crespi, C.L.1    Penman, B.W.2    Hu, M.3


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