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Volumn 45, Issue 5, 2007, Pages 871-877

Cytotoxicity of chloroacetanilide herbicide alachlor in HepG2 cells independent of CYP3A4 and CYP3A7

Author keywords

2 chloro 2 ,6 diethyl N (methoxymethyl) acetanilide; Chloroacetanilide herbicides; DPX 2 cells; Hepatotoxicity; N dealkylation

Indexed keywords

2,6 DIETHYLBENZOQUINONIMINE; ACETANILIDE; ALACHLOR; BENZYL DERIVATIVE; CYTOCHROME P450 3A4; CYTOCHROME P450 3A7; DEXAMETHASONE; ETHER DERIVATIVE; HERBICIDE; LACTATE DEHYDROGENASE; LUCIFERIN; PREGNANE X RECEPTOR; RIFAMPICIN; TROLEANDOMYCIN; UNCLASSIFIED DRUG;

EID: 33947423329     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2006.11.011     Document Type: Article
Times cited : (16)

References (47)
  • 5
    • 0033835442 scopus 로고    scopus 로고
    • Catalysis of the 4-hydroxylation of retinoic acid by CYP3A7 in human fetal hepatic tissues
    • Chen H., Fantel A.G., and Juchau M.R. Catalysis of the 4-hydroxylation of retinoic acid by CYP3A7 in human fetal hepatic tissues. Drug Metab. Dispos. 28 (2000) 1051-1057
    • (2000) Drug Metab. Dispos. , vol.28 , pp. 1051-1057
    • Chen, H.1    Fantel, A.G.2    Juchau, M.R.3
  • 6
    • 0032867074 scopus 로고    scopus 로고
    • In vitro metabolism of alachlor by human liver microsomes and human cytochrome P450 isoforms
    • Coleman S., Liu S., Linderman R., Hodgson E., and Rose R.L. In vitro metabolism of alachlor by human liver microsomes and human cytochrome P450 isoforms. Chem.-Biol. Interact. 122 (1999) 27-39
    • (1999) Chem.-Biol. Interact. , vol.122 , pp. 27-39
    • Coleman, S.1    Liu, S.2    Linderman, R.3    Hodgson, E.4    Rose, R.L.5
  • 7
    • 0034523338 scopus 로고    scopus 로고
    • Comparative metabolism of chloroacetanilide herbicides and selected metabolites in human and rat liver microsomes
    • Coleman S., Linderman R., Hodgson E., and Rose R.L. Comparative metabolism of chloroacetanilide herbicides and selected metabolites in human and rat liver microsomes. Environ. Health Perspect. 108 (2000) 1151-1157
    • (2000) Environ. Health Perspect. , vol.108 , pp. 1151-1157
    • Coleman, S.1    Linderman, R.2    Hodgson, E.3    Rose, R.L.4
  • 8
    • 0028114942 scopus 로고
    • Cytosolic activation of aromatic and heterocyclic amines. Inhibition by dicoumarol and enhancement in viral hepatitis B
    • De Flora S., Bennicelli C., D'Agostini F., Izzotti A., and Camoirano A. Cytosolic activation of aromatic and heterocyclic amines. Inhibition by dicoumarol and enhancement in viral hepatitis B. Environ. Health Perspect. 102 (1994) 69-74
    • (1994) Environ. Health Perspect. , vol.102 , pp. 69-74
    • De Flora, S.1    Bennicelli, C.2    D'Agostini, F.3    Izzotti, A.4    Camoirano, A.5
  • 9
    • 0033495123 scopus 로고    scopus 로고
    • Glutathione-dependent cytotoxicity of the chloroacetanilide herbicides alachlor, metolachlor, and propachlor in rat and human hepatoma-derived cultured cells
    • Dierickx P.J. Glutathione-dependent cytotoxicity of the chloroacetanilide herbicides alachlor, metolachlor, and propachlor in rat and human hepatoma-derived cultured cells. Cell Biol. Toxicol. 15 (1999) 325-332
    • (1999) Cell Biol. Toxicol. , vol.15 , pp. 325-332
    • Dierickx, P.J.1
  • 10
    • 0028835204 scopus 로고
    • Drug toxicity mechanisms in human hepatoma HepG2 cells: cyclosporin A and tamoxifen
    • Duthie S.J., Melvin W.T., and Burke M.D. Drug toxicity mechanisms in human hepatoma HepG2 cells: cyclosporin A and tamoxifen. Xenobiotica 25 (1995) 1151-1164
    • (1995) Xenobiotica , vol.25 , pp. 1151-1164
    • Duthie, S.J.1    Melvin, W.T.2    Burke, M.D.3
  • 11
  • 12
    • 0024592407 scopus 로고
    • In vitro oxidation of alachlor by liver microsomal enzymes from rats, mice, and monkeys
    • Feng P.C., and Patanella J.E. In vitro oxidation of alachlor by liver microsomal enzymes from rats, mice, and monkeys. Pestic. Biochem. Physiol. 33 (1989) 16-25
    • (1989) Pestic. Biochem. Physiol. , vol.33 , pp. 16-25
    • Feng, P.C.1    Patanella, J.E.2
  • 14
    • 0031865903 scopus 로고    scopus 로고
    • Determination of serum levels of 2,6 diethylaniline in laboratory animal treated with alachlor
    • Galati R., Federico A., Cortese G., and Zito R. Determination of serum levels of 2,6 diethylaniline in laboratory animal treated with alachlor. Anticancer Res. 18 (1998) 979-982
    • (1998) Anticancer Res. , vol.18 , pp. 979-982
    • Galati, R.1    Federico, A.2    Cortese, G.3    Zito, R.4
  • 15
    • 5044251490 scopus 로고    scopus 로고
    • Update on olfactory mucosal metabolic enzymes: age-related changes and N-acetyltransferase activities
    • Genter M.B. Update on olfactory mucosal metabolic enzymes: age-related changes and N-acetyltransferase activities. J. Biochem. Mol. Toxicol. 18 (2004) 239-244
    • (2004) J. Biochem. Mol. Toxicol. , vol.18 , pp. 239-244
    • Genter, M.B.1
  • 16
    • 0036166288 scopus 로고    scopus 로고
    • Effect of alachlor on hepatic cytochrome P450 enzymes in rats
    • Hanioka N., Watanabe K., Yoda R., and Ando M. Effect of alachlor on hepatic cytochrome P450 enzymes in rats. Drug Chem. Toxicol. 25 (2002) 25-37
    • (2002) Drug Chem. Toxicol. , vol.25 , pp. 25-37
    • Hanioka, N.1    Watanabe, K.2    Yoda, R.3    Ando, M.4
  • 17
    • 0030007481 scopus 로고    scopus 로고
    • Influence of DT diaphorase on quinine-mediated genotoxicity in human and fish cell lines
    • Hasspieler B.M., Haffner G.D., and Adeli K. Influence of DT diaphorase on quinine-mediated genotoxicity in human and fish cell lines. Mutat. Res. 360 (1996) 43-49
    • (1996) Mutat. Res. , vol.360 , pp. 43-49
    • Hasspieler, B.M.1    Haffner, G.D.2    Adeli, K.3
  • 18
    • 1842627852 scopus 로고    scopus 로고
    • Phase I and II enzyme characterization of two sources of HepG2 cell lines
    • Hewitt N.J., and Hewitt P. Phase I and II enzyme characterization of two sources of HepG2 cell lines. Xenobiotica 34 (2004) 243-256
    • (2004) Xenobiotica , vol.34 , pp. 243-256
    • Hewitt, N.J.1    Hewitt, P.2
  • 20
    • 0031565920 scopus 로고    scopus 로고
    • Diaklyquinoneimine metabolites of chloroacetanilide herbicides induce sister chromatid exchanges in cultured human lymphocytes
    • Hill A.B., Jefferies P.R., Quistad G.B., and Casida J.E. Diaklyquinoneimine metabolites of chloroacetanilide herbicides induce sister chromatid exchanges in cultured human lymphocytes. Mutat. Res. 395 (1997) 159-171
    • (1997) Mutat. Res. , vol.395 , pp. 159-171
    • Hill, A.B.1    Jefferies, P.R.2    Quistad, G.B.3    Casida, J.E.4
  • 21
    • 0001417564 scopus 로고
    • Alachlor and its analogues as metabolic progenitors of formaldehyde: fate of N-methoxymethyl and other N-alkoxyalkyl substituents
    • Jacobsen N.E., Sanders M., Toja R.F., and Casida J.E. Alachlor and its analogues as metabolic progenitors of formaldehyde: fate of N-methoxymethyl and other N-alkoxyalkyl substituents. J. Agric. Food Chem. 39 (1991) 1342-1350
    • (1991) J. Agric. Food Chem. , vol.39 , pp. 1342-1350
    • Jacobsen, N.E.1    Sanders, M.2    Toja, R.F.3    Casida, J.E.4
  • 22
    • 0031949445 scopus 로고    scopus 로고
    • Dialkylquinoneimines validated as in vivo metabolites of alachlor, acetochlor, and metolachlor herbicides in rats
    • Jefferies P.R., Quistad G.B., and Casida J.E. Dialkylquinoneimines validated as in vivo metabolites of alachlor, acetochlor, and metolachlor herbicides in rats. Chem. Res. Toxicol. 11 (1998) 353-359
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 353-359
    • Jefferies, P.R.1    Quistad, G.B.2    Casida, J.E.3
  • 25
    • 17844365030 scopus 로고    scopus 로고
    • Chemopreventive properties of trans-resveratrol against the cytotoxicity of chloroacetanilide herbicide in vitro
    • Kocsis Z., Marcsek Z.L., Jakab M.G., Szende B., and Tompa A. Chemopreventive properties of trans-resveratrol against the cytotoxicity of chloroacetanilide herbicide in vitro. Int. J. Hyg. Environ. Health 208 (2005) 211-218
    • (2005) Int. J. Hyg. Environ. Health , vol.208 , pp. 211-218
    • Kocsis, Z.1    Marcsek, Z.L.2    Jakab, M.G.3    Szende, B.4    Tompa, A.5
  • 26
    • 0037432689 scopus 로고    scopus 로고
    • Differential drug-induced mRNA expression of human CYP3A4 compared to CYP3A5, CYP3A7 and CYP3A43
    • Krusekopf S., Roots I., and Kleeberg U. Differential drug-induced mRNA expression of human CYP3A4 compared to CYP3A5, CYP3A7 and CYP3A43. Eur. J. Pharmacol. 466 (2003) 7-12
    • (2003) Eur. J. Pharmacol. , vol.466 , pp. 7-12
    • Krusekopf, S.1    Roots, I.2    Kleeberg, U.3
  • 29
    • 33947382023 scopus 로고    scopus 로고
    • Comparative hepatotoxicity of chloroacetanilide herbicides alachlor and metolachlor
    • (Abst. # 261)
    • Meyer S.A., and Dalton S.R. Comparative hepatotoxicity of chloroacetanilide herbicides alachlor and metolachlor. The Toxicologist 60 (2001) 54 (Abst. # 261)
    • (2001) The Toxicologist , vol.60 , pp. 54
    • Meyer, S.A.1    Dalton, S.R.2
  • 31
    • 29944434772 scopus 로고    scopus 로고
    • Selective suppressions of human CYP3A forms, CYP3A5 and CYP3A7, by troglitazone in HepG2 cells
    • Ogino M., Nagata K., and Yamazone Y. Selective suppressions of human CYP3A forms, CYP3A5 and CYP3A7, by troglitazone in HepG2 cells. Drug. Metab. Pharmacokinet. 17 (2002) 42-46
    • (2002) Drug. Metab. Pharmacokinet. , vol.17 , pp. 42-46
    • Ogino, M.1    Nagata, K.2    Yamazone, Y.3
  • 32
    • 0032496311 scopus 로고    scopus 로고
    • Differential catalytic properties in metabolism of endogenous and exogenous substrates among CYP3A enzymes expressed in COS-7 cells
    • Ohmori S., Nakasa H., Asanome K., Kurose Y., Ishii I., Hosokawa M., and Kitada M. Differential catalytic properties in metabolism of endogenous and exogenous substrates among CYP3A enzymes expressed in COS-7 cells. Biochim. Biophys. Acta 1380 (1998) 297-304
    • (1998) Biochim. Biophys. Acta , vol.1380 , pp. 297-304
    • Ohmori, S.1    Nakasa, H.2    Asanome, K.3    Kurose, Y.4    Ishii, I.5    Hosokawa, M.6    Kitada, M.7
  • 33
    • 0030056594 scopus 로고    scopus 로고
    • Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes
    • Ono S., Hatanaka T., Hotta H., Satoh T., Gonzalez F.J., and Tsutsui M. Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes. Xenobiotica 26 (1996) 681-693
    • (1996) Xenobiotica , vol.26 , pp. 681-693
    • Ono, S.1    Hatanaka, T.2    Hotta, H.3    Satoh, T.4    Gonzalez, F.J.5    Tsutsui, M.6
  • 34
    • 0035659943 scopus 로고    scopus 로고
    • Dual effect of dexamethasone on CYP3A4 gene expression in human hepatocytes. Sequential role of glucocorticoid receptor and pregnane X receptor
    • Pascussi J.M., Droucourt L., Gerbal-Chaloin S., Fabre J.M., Maurel P., and Vilarem M.J. Dual effect of dexamethasone on CYP3A4 gene expression in human hepatocytes. Sequential role of glucocorticoid receptor and pregnane X receptor. Eur. J. Biochem. 268 (2001) 6346-6358
    • (2001) Eur. J. Biochem. , vol.268 , pp. 6346-6358
    • Pascussi, J.M.1    Droucourt, L.2    Gerbal-Chaloin, S.3    Fabre, J.M.4    Maurel, P.5    Vilarem, M.J.6
  • 36
    • 0036784511 scopus 로고    scopus 로고
    • A cell-based reporter gene assay for determining induction of CYP3A4 in a high-volume system
    • Raucy J., Warfe L., Yueh M.F., and Allen S.W. A cell-based reporter gene assay for determining induction of CYP3A4 in a high-volume system. J. Pharmacol. Exp. Ther. 303 (2002) 412-423
    • (2002) J. Pharmacol. Exp. Ther. , vol.303 , pp. 412-423
    • Raucy, J.1    Warfe, L.2    Yueh, M.F.3    Allen, S.W.4
  • 37
    • 0036301269 scopus 로고    scopus 로고
    • Cytochrome P450 expression in human hepatocytes and hepatoma cell lines: molecular mechanisms that determine lower expression in cultured cells
    • Rodriguez-Antona C., Donato M.T., Boobis A., Edwards R.J., Watts P.S., Castell J.V., and Gomez-Lechon M.J. Cytochrome P450 expression in human hepatocytes and hepatoma cell lines: molecular mechanisms that determine lower expression in cultured cells. Xenobiotica 32 (2002) 505-520
    • (2002) Xenobiotica , vol.32 , pp. 505-520
    • Rodriguez-Antona, C.1    Donato, M.T.2    Boobis, A.3    Edwards, R.J.4    Watts, P.S.5    Castell, J.V.6    Gomez-Lechon, M.J.7
  • 38
    • 0035080719 scopus 로고    scopus 로고
    • In vitro long-term cytotoxicity testing of 27 MEIC chemicals on HepG2 cells and comparison with acute human toxicity data
    • Scheers E.M., Ekwall B., and Dierickx P.J. In vitro long-term cytotoxicity testing of 27 MEIC chemicals on HepG2 cells and comparison with acute human toxicity data. Toxicol. In Vitro 15 (2001) 153-161
    • (2001) Toxicol. In Vitro , vol.15 , pp. 153-161
    • Scheers, E.M.1    Ekwall, B.2    Dierickx, P.J.3
  • 41
    • 33947410158 scopus 로고    scopus 로고
    • Assessing the role of CYP3A5 and CYP3A7 in drug-drug interactions
    • (Abstract # 613)
    • Stressor D.M., Turner S.D., Ho T., and Crespi C.L. Assessing the role of CYP3A5 and CYP3A7 in drug-drug interactions. The Toxicologist (2002) 66 (Abstract # 613)
    • (2002) The Toxicologist , pp. 66
    • Stressor, D.M.1    Turner, S.D.2    Ho, T.3    Crespi, C.L.4
  • 42
    • 27644553953 scopus 로고    scopus 로고
    • A simultaneous assessment of CYp3A4 metabolism and induction in the DPX-2 cell line
    • Trubetskoy O., Marks B., Zielinski T., Yueh M.F., and Raucy J. A simultaneous assessment of CYp3A4 metabolism and induction in the DPX-2 cell line. AAPS J. 7 (2005) E6-E13
    • (2005) AAPS J. , vol.7
    • Trubetskoy, O.1    Marks, B.2    Zielinski, T.3    Yueh, M.F.4    Raucy, J.5
  • 43
    • 33947380387 scopus 로고    scopus 로고
    • USEPA, 1998. Reregistration Eligibility Decision (RED). Alachlor. Office of Pesticide Programs. EPA-738-R-98-020.
  • 44
    • 0032998384 scopus 로고    scopus 로고
    • Evidence for site-specific bioactivation of alachlor in the olfactory mucosa of the Long-Evans rat
    • Wetmore B.A., Mitchell A.D., Meyer S.A., and Genter M.B. Evidence for site-specific bioactivation of alachlor in the olfactory mucosa of the Long-Evans rat. Toxicol. Sci. 49 (1999) 202-212
    • (1999) Toxicol. Sci. , vol.49 , pp. 202-212
    • Wetmore, B.A.1    Mitchell, A.D.2    Meyer, S.A.3    Genter, M.B.4
  • 45
    • 0042065286 scopus 로고    scopus 로고
    • Influence of culture time on the expression of drug-metabolizing enzymes in primary human hepatocytes and hepatoma cell line HepG2
    • Wilkening S., and Bader A. Influence of culture time on the expression of drug-metabolizing enzymes in primary human hepatocytes and hepatoma cell line HepG2. J. Biochem. Mol. Toxicol. 17 (2003) 207-213
    • (2003) J. Biochem. Mol. Toxicol. , vol.17 , pp. 207-213
    • Wilkening, S.1    Bader, A.2
  • 46
    • 0042904900 scopus 로고    scopus 로고
    • Comparison of primary human hepatocytes and hepatoma cell line HepG2 with regard to their biotransformation properties
    • Wilkening S., Stahl F., and Bader A. Comparison of primary human hepatocytes and hepatoma cell line HepG2 with regard to their biotransformation properties. Drug Metab. Dispos. 31 (2003) 1035-1042
    • (2003) Drug Metab. Dispos. , vol.31 , pp. 1035-1042
    • Wilkening, S.1    Stahl, F.2    Bader, A.3
  • 47
    • 11144349691 scopus 로고    scopus 로고
    • High volume bioassays to assess CYP3A4-mediated drug interactions: induction and inhibition in a single cell line
    • Yueh M.F., Kawahara M., and Raucy J. High volume bioassays to assess CYP3A4-mediated drug interactions: induction and inhibition in a single cell line. Drug Metab. Dispos. 33 (2005) 38-48
    • (2005) Drug Metab. Dispos. , vol.33 , pp. 38-48
    • Yueh, M.F.1    Kawahara, M.2    Raucy, J.3


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