메뉴 건너뛰기




Volumn 40, Issue 3, 2012, Pages 596-601

Trapping of cis-2-butene-1,4-dial to measure furan metabolism in human liver microsomes by cytochrome P450 enzymes

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENOL HYDROXYLASE; ACETYLCYSTEINE; ALDEHYDE DERIVATIVE; AMINO ACID; CIS 2 BUTENE 1,4 DIAL; CYTOCHROME P450; CYTOCHROME P450 2E1; CYTOCHROME P450 INHIBITOR; FURAN; N ACETYL [1 (5 ACETYLAMINO 5 CARBOXYPENTYL) 1H PYRROL 3 YL]CYSTEINE; N ACETYL LYSINE; OXYGENASE; UNCLASSIFIED DRUG;

EID: 84857418739     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.043679     Document Type: Article
Times cited : (40)

References (39)
  • 1
    • 18944393300 scopus 로고    scopus 로고
    • Bioactivation of 4-ipomeanol by CYP4B1: Adduct characterization and evidence for an enedial intermediate
    • DOI 10.1021/tx0496993
    • Baer BR, Rettie AE, and Henne KR (2005) Bioactivation of 4-ipomeanol by CYP4B1: adduct characterization and evidence for an enedial intermediate. Chem Res Toxicol 18:855-864. (Pubitemid 40705452)
    • (2005) Chemical Research in Toxicology , vol.18 , Issue.5 , pp. 855-864
    • Baer, B.R.1    Rettie, A.E.2    Henne, K.R.3
  • 2
    • 34547899883 scopus 로고    scopus 로고
    • Reverse transcriptase-PCR quantification of mRNA levels from cytochrome (CYP)1, CYP2 and CYP3 families in 22 different human tissues
    • DOI 10.1097/FPC.0b013e32810f2e58, PII 0121301120070900000006
    • Bièche I, Narjoz C, Asselah T, Vacher S, Marcellin P, Lidereau R, Beaune P, and de Waziers I (2007) Reverse transcriptase-PCR quantification of mRNA levels from cytochrome (CYP)1, CYP2 and CYP3 families in 22 different human tissues. Pharmacogenet Genomics 17:731-742. (Pubitemid 47263068)
    • (2007) Pharmacogenetics and Genomics , vol.17 , Issue.9 , pp. 731-742
    • Bieche, I.1    Narjoz, C.2    Asselah, T.3    Vacher, S.4    Marcellin, P.5    Lidereau, R.6    Beaune, P.7    De Waziers, I.8
  • 3
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254.
    • (1976) Anal Biochem , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 4
    • 0036129082 scopus 로고    scopus 로고
    • Characterization of nucleoside adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan
    • DOI 10.1021/tx0101402
    • Byrns MC, Predecki DP, and Peterson LA (2002) Characterization of nucleoside adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem Res Toxicol 15:373-379. (Pubitemid 34241376)
    • (2002) Chemical Research in Toxicology , vol.15 , Issue.3 , pp. 373-379
    • Byrns, M.C.1    Predecki, D.P.2    Peterson, L.A.3
  • 5
    • 10844243981 scopus 로고    scopus 로고
    • 2-etheno-2′-deoxyguanosine adducts by cis-2-butene-1,4-dial, a reactive metabolite of furan
    • 2-etheno- 2′-deoxyguanosine adducts by cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem Res Toxicol 17:1607-1613.
    • (2004) Chem Res Toxicol , vol.17 , pp. 1607-1613
    • Byrns, M.C.1    Vu, C.C.2    Peterson, L.A.3
  • 6
    • 0015538457 scopus 로고
    • Effects of exposure to solvents caused by air pollution with special reference to CCl 4 and its distribution in air
    • Capurro PU (1973) Effects of exposure to solvents caused by air pollution with special reference to CCl 4 and its distribution in air. Clin Toxicol 6:109-124.
    • (1973) Clin Toxicol , vol.6 , pp. 109-124
    • Capurro, P.U.1
  • 7
    • 0027377274 scopus 로고
    • Furan-induced cytolethality in isolated rat hepatocytes: Correspondence with in vivo dosimetry
    • DOI 10.1006/taap.1993.1245
    • Carfagna MA, Held SD, and Kedderis GL (1993) Furan-induced cytolethality in isolated rat hepatocytes: correspondence with in vivo dosimetry. Toxicol Appl Pharmacol 123:265-273. (Pubitemid 23359269)
    • (1993) Toxicology and Applied Pharmacology , vol.123 , Issue.2 , pp. 265-273
    • Carfagna, M.A.1    Held, S.D.2    Kedderis, G.L.3
  • 8
    • 33745125943 scopus 로고    scopus 로고
    • Spectrophotometric analysis of human CYP2E1-catalyzed p-nitrophenol hydroxylation
    • Chang TK, Crespi CL, and Waxman DJ (2006) Spectrophotometric analysis of human CYP2E1-catalyzed p-nitrophenol hydroxylation. Methods Mol Biol 320:127-131.
    • (2006) Methods Mol Biol , vol.320 , pp. 127-131
    • Chang, T.K.1    Crespi, C.L.2    Waxman, D.J.3
  • 9
    • 0028785113 scopus 로고
    • Identification of cis-2-butene-1,4-dial as a microsomal metabolite of furan
    • Chen LJ, Hecht SS, and Peterson LA (1995) Identification of cis-2-butene-1,4-dial as a microsomal metabolite of furan. Chem Res Toxicol 8:903-906.
    • (1995) Chem Res Toxicol , vol.8 , pp. 903-906
    • Chen, L.J.1    Hecht, S.S.2    Peterson, L.A.3
  • 10
    • 0030753035 scopus 로고    scopus 로고
    • Characterization of amino acid and glutathione adducts of cis-2-butene- 1,4-dial, a reactive metabolite of furan
    • DOI 10.1021/tx9700174
    • Chen LJ, Hecht SS, and Peterson LA (1997) Characterization of amino acid and glutathione adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem Res Toxicol 10:866-874. (Pubitemid 27350045)
    • (1997) Chemical Research in Toxicology , vol.10 , Issue.8 , pp. 866-874
    • Chen, L.-J.1    Hecht, S.S.2    Peterson, L.A.3
  • 11
    • 0041764982 scopus 로고    scopus 로고
    • CYP2E1 activity before and after weight loss in morbidly obese subjects with nonalcoholic fatty liver disease
    • DOI 10.1053/jhep.2003.50342
    • Emery MG, Fisher JM, Chien JY, Kharasch ED, Dellinger EP, Kowdley KV, and Thummel KE (2003) CYP2E1 activity before and after weight loss in morbidly obese subjects with nonalcoholic fatty liver disease. Hepatology 38:428-435. (Pubitemid 36919864)
    • (2003) Hepatology , vol.38 , Issue.2 , pp. 428-435
    • Emery, M.G.1    Fisher, J.M.2    Chien, J.Y.3    Kharasch, E.D.4    Dellinger, E.P.5    Kowdley, K.V.6    Thummel, K.E.7
  • 12
    • 0034826977 scopus 로고    scopus 로고
    • Reaction of cis- and trans-2-butene-1,4-dial with 2′-deoxycytidine to form stable oxadiazabicyclooctaimine adducts
    • DOI 10.1021/ja0056421
    • Gingipalli L and Dedon PC (2001) Reaction of cis- and trans-2-butene-1,4-dial with 2′-deoxycytidine to form stable oxadiazabicyclooctaimine adducts. J Am Chem Soc 123:2664-2665. (Pubitemid 32888568)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.11 , pp. 2664-2665
    • Gingipalli, L.1    Dedon, P.C.2
  • 13
    • 0001818451 scopus 로고
    • Microsomal enzymes involved in toxicology-analysis and separation
    • Hayes AW ed Raven Press, New York
    • Guengerich FP (1982) Microsomal enzymes involved in toxicology-analysis and separation, in Principles and Methods of Toxicology (Hayes AW ed) pp 609-634, Raven Press, New York.
    • (1982) Principles and Methods of Toxicology , pp. 609-634
    • Guengerich, F.P.1
  • 14
    • 0026035519 scopus 로고
    • Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects
    • Guengerich FP, Kim DH, and Iwasaki M (1991) Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem Res Toxicol 4:168-179.
    • (1991) Chem Res Toxicol , vol.4 , pp. 168-179
    • Guengerich, F.P.1    Kim, D.H.2    Iwasaki, M.3
  • 15
    • 77957122944 scopus 로고    scopus 로고
    • Hepatobiliary toxicity of furan: Identification of furan metabolites in bile of male f344/n rats
    • Hamberger C, Kellert M, Schauer UM, Dekant W, and Mally A (2010) Hepatobiliary toxicity of furan: identification of furan metabolites in bile of male f344/n rats. Drug Metab Dispos 38:1698-1706.
    • (2010) Drug Metab Dispos , vol.38 , pp. 1698-1706
    • Hamberger, C.1    Kellert, M.2    Schauer, U.M.3    Dekant, W.4    Mally, A.5
  • 16
    • 33846458275 scopus 로고    scopus 로고
    • The importance of cytochrome P450 2B6 in the human metabolism of environmental chemicals
    • DOI 10.1016/j.pharmthera.2006.10.002, PII S0163725806001859
    • Hodgson E and Rose RL (2007) The importance of cytochrome P450 2B6 in the human metabolism of environmental chemicals. Pharmacol Ther 113:420-428. (Pubitemid 46149054)
    • (2007) Pharmacology and Therapeutics , vol.113 , Issue.2 , pp. 420-428
    • Hodgson, E.1    Rose, R.L.2
  • 19
    • 0030246901 scopus 로고    scopus 로고
    • Prediction of furan pharmacokinetics from hepatocyte studies: Comparison of bioactivation and hepatic dosimetry in rats, mice, and humans'
    • DOI 10.1006/taap.1996.0205
    • Kedderis GL and Held SD (1996) Prediction of furan pharmacokinetics from hepatocyte studies: comparison of bioactivation and hepatic dosimetry in rats, mice, and humans. Toxicol Appl Pharmacol 140:124-130. (Pubitemid 26329470)
    • (1996) Toxicology and Applied Pharmacology , vol.140 , Issue.1 , pp. 124-130
    • Kedderis, G.L.1    Held, S.D.2
  • 20
    • 56249144108 scopus 로고    scopus 로고
    • Tests for genotoxicity and mutagenicity of furan and its metabolite cis-2-butene-1,4-dial in L5178Y tk+/- mouse lymphoma cells
    • Kellert M, Brink A, Richter I, Schlatter J, and Lutz WK (2008a) Tests for genotoxicity and mutagenicity of furan and its metabolite cis-2-butene-1,4-dial in L5178Y tk+/- mouse lymphoma cells. Mutat Res 657:127-132.
    • (2008) Mutat Res , vol.657 , pp. 127-132
    • Kellert, M.1    Brink, A.2    Richter, I.3    Schlatter, J.4    Lutz, W.K.5
  • 21
    • 41849111307 scopus 로고    scopus 로고
    • Biomarkers of furan exposure by metabolic profiling of rat urine with liquid chromatography-tandem mass spectrometry and principal component analysis
    • DOI 10.1021/tx7004212
    • Kellert M, Wagner S, Lutz U, and Lutz WK (2008b) Biomarkers of furan exposure by metabolic profiling of rat urine with liquid chromatography-tandem mass spectrometry and principal component analysis. Chem Res Toxicol 21:761-768. (Pubitemid 351498054)
    • (2008) Chemical Research in Toxicology , vol.21 , Issue.3 , pp. 761-768
    • Kellert, M.1    Wagner, S.2    Lutz, U.3    Lutz, W.K.4
  • 22
    • 0030935567 scopus 로고    scopus 로고
    • Cytochrome P-4502E1: Its physiological and pathological role
    • Lieber CS (1997) Cytochrome P-4502E1: its physiological and pathological role. Physiol Rev 77:517-544.
    • (1997) Physiol Rev , vol.77 , pp. 517-544
    • Lieber, C.S.1
  • 23
    • 75149124058 scopus 로고    scopus 로고
    • Identification of furan metabolites derived from cysteine-cis-2-butene-1, 4-dial-lysine cross-links
    • Lu D and Peterson LA (2010) Identification of furan metabolites derived from cysteine-cis-2-butene-1,4-dial-lysine cross-links. Chem Res Toxicol 23:142-151.
    • (2010) Chem Res Toxicol , vol.23 , pp. 142-151
    • Lu, D.1    Peterson, L.A.2
  • 24
    • 67449104867 scopus 로고    scopus 로고
    • Degraded protein adducts of cis-2-butene-1,4-dial are urinary and hepatocyte metabolites of furan
    • Lu D, Sullivan MM, Phillips MB, and Peterson LA (2009) Degraded protein adducts of cis-2-butene-1,4-dial are urinary and hepatocyte metabolites of furan. Chem Res Toxicol 22:997-1007.
    • (2009) Chem Res Toxicol , vol.22 , pp. 997-1007
    • Lu, D.1    Sullivan, M.M.2    Phillips, M.B.3    Peterson, L.A.4
  • 26
    • 0021732385 scopus 로고
    • DNA-damaging activity of biotic and xenobiotic aldehydes in Chinese hamster ovary cells
    • DOI 10.1002/cbf.290020411
    • Marinari UM, Ferro M, Sciaba L, Finollo R, Bassi AM, and Brambilla G (1984) DNA-damaging activity of biotic and xenobiotic aldehydes in Chinese hamster ovary cells. Cell Biochem Funct 2:243-248. (Pubitemid 15218600)
    • (1984) Cell Biochemistry and Function , vol.2 , Issue.4 , pp. 243-248
    • Marinari, U.M.1    Ferro, M.2    Sciaba, L.3
  • 27
    • 0003541547 scopus 로고
    • Toxicology and carcinogenesis studies of furan in F344/N rats and B6C3F1 mice
    • National Toxicology Program US Department of Health and Human Services, Public Health Service, National Institutes of Health, Research Triangle Park, NC
    • National Toxicology Program (1993) Toxicology and carcinogenesis studies of furan in F344/N rats and B6C3F1 mice. [NTP Technical Report No. 402]. US Department of Health and Human Services, Public Health Service, National Institutes of Health, Research Triangle Park, NC.
    • (1993) NTP Technical Report No. 402
  • 28
    • 80053648469 scopus 로고    scopus 로고
    • National Toxicology Program U.S. Department of Health and Human Services, Washington, DC
    • National Toxicology Program (2011) 12th Report on Carcinogens. U.S. Department of Health and Human Services, Washington, DC.
    • (2011) 12th Report on Carcinogens
  • 30
    • 75749116800 scopus 로고    scopus 로고
    • Genetic polymorphism in cytochrome P450 2D6 (CYP2D6): Population distribution of CYP2D6 activity
    • Neafsey P, Ginsberg G, Hattis D, and Sonawane B (2009b) Genetic polymorphism in cytochrome P450 2D6 (CYP2D6): Population distribution of CYP2D6 activity. J Toxicol Environ Health B Crit Rev 12:334-361.
    • (2009) J Toxicol Environ Health B Crit Rev , vol.12 , pp. 334-361
    • Neafsey, P.1    Ginsberg, G.2    Hattis, D.3    Sonawane, B.4
  • 32
    • 0027564724 scopus 로고
    • Studies on the interaction of furan with hepatic cytochrome P-450
    • Parmar D and Burka LT (1993) Studies on the interaction of furan with hepatic cytochrome P-450. J Biochem Toxicol 8:1-9.
    • (1993) J Biochem Toxicol , vol.8 , pp. 1-9
    • Parmar, D.1    Burka, L.T.2
  • 33
    • 33748997091 scopus 로고    scopus 로고
    • Identification of a cis-2-butene-1,4-dial-derived glutathione conjugate in the urine of furan-treated rats
    • DOI 10.1021/tx060111x
    • Peterson LA, Cummings ME, Chan JY, Vu CC, and Matter BA (2006) Identification of a cis-2-butene-1,4-dial-derived glutathione conjugate in the urine of furan-treated rats. Chem Res Toxicol 19:1138-1141. (Pubitemid 44454029)
    • (2006) Chemical Research in Toxicology , vol.19 , Issue.9 , pp. 1138-1141
    • Peterson, L.A.1    Cummings, M.E.2    Chan, J.Y.3    Vu, C.C.4    Matter, B.A.5
  • 34
    • 24944560423 scopus 로고    scopus 로고
    • Glutathione trapping to measure microsomal oxidation of furan to cis-2-butene-1,4-dial
    • DOI 10.1124/dmd.105.004432
    • Peterson LA, Cummings ME, Vu CC, and Matter BA (2005) Glutathione trapping to measure microsomal oxidation of furan to cis-2-butene-1,4-dial. Drug Metab Dispos 33:1453-1458. (Pubitemid 41323992)
    • (2005) Drug Metabolism and Disposition , vol.33 , Issue.10 , pp. 1453-1458
    • Peterson, L.A.1    Cummings, M.E.2    Vu, C.C.3    Matter, B.A.4
  • 35
    • 0033914808 scopus 로고    scopus 로고
    • A reactive metabolite of furan, cis-2-butene-1,4-dial, is mutagenic in the Ames assay
    • DOI 10.1021/tx000065f
    • Peterson LA, Naruko KC, and Predecki DP (2000) A reactive metabolite of furan, cis-2-butene-1,4-dial, is mutagenic in the Ames assay. Chem Res Toxicol 13:531-534. (Pubitemid 30491112)
    • (2000) Chemical Research in Toxicology , vol.13 , Issue.7 , pp. 531-534
    • Peterson, L.A.1    Naruko, K.C.2    Predecki, D.P.3
  • 36
    • 81755172321 scopus 로고    scopus 로고
    • Polyamines are traps for reactive intermediates in furan metabolism
    • Peterson LA, Phillips MB, Lu D, and Sullivan MM (2011) Polyamines are traps for reactive intermediates in furan metabolism. Chem Res Toxicol 24:1924-1936.
    • (2011) Chem Res Toxicol , vol.24 , pp. 1924-1936
    • Peterson, L.A.1    Phillips, M.B.2    Lu, D.3    Sullivan, M.M.4
  • 37
    • 0028237729 scopus 로고
    • Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians
    • Shimada T, Yamazaki H, Mimura M, Inui Y, and Guengerich FP (1994) Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 270:414-423. (Pubitemid 24229655)
    • (1994) Journal of Pharmacology and Experimental Therapeutics , vol.270 , Issue.1 , pp. 414-423
    • Shimada, T.1    Yamazaki, H.2    Mimura, M.3    Inui, Y.4    Guengerich, F.P.5
  • 39
    • 52449133102 scopus 로고    scopus 로고
    • CYP2B6: New insights into a historically overlooked cytochrome P450 isozyme
    • Wang H and Tompkins LM (2008) CYP2B6: new insights into a historically overlooked cytochrome P450 isozyme. Curr Drug Metab 9:598-610.
    • (2008) Curr Drug Metab , vol.9 , pp. 598-610
    • Wang, H.1    Tompkins, L.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.