메뉴 건너뛰기




Volumn 18, Issue 5, 2005, Pages 896-903

Dansyl glutathione as a trapping agent for the quantitative estimation and identification of reactive metabolites

Author keywords

[No Author keywords available]

Indexed keywords

1 CHLORO 2,4 DINITROBENZENE; DANSYL CHLORIDE; GLUTATHIONE; GLUTATHIONE DISULFIDE; PULEGONE;

EID: 18944396519     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0496791     Document Type: Article
Times cited : (155)

References (42)
  • 1
    • 0032789796 scopus 로고    scopus 로고
    • New concepts in immunology relevant to idiosyncratic drug reactions: The "danger hypothesis" and innate immune system
    • Uetrecht, J. P. (1999) New concepts in immunology relevant to idiosyncratic drug reactions: the "danger hypothesis" and innate immune system. Chem. Res. Toxicol. 12, 387-395.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 387-395
    • Uetrecht, J.P.1
  • 2
    • 0034676475 scopus 로고    scopus 로고
    • Advances in molecular toxicology-towards understanding idiosyncratic drug toxicity
    • Park, B. K., Kitteringham, N. R., Powell, H., and Pirmohamed, M. (2000) Advances in molecular toxicology-towards understanding idiosyncratic drug toxicity. Toxicology 153, 39-60.
    • (2000) Toxicology , vol.153 , pp. 39-60
    • Park, B.K.1    Kitteringham, N.R.2    Powell, H.3    Pirmohamed, M.4
  • 3
    • 0037058253 scopus 로고    scopus 로고
    • A review of the common properties of drugs with idiosyncratic hepatotoxicity and the "multiple determinant hypothesis" for the manifestation of idiosyncratic drug toxicity
    • Li, A. P. (2002) A review of the common properties of drugs with idiosyncratic hepatotoxicity and the "multiple determinant hypothesis" for the manifestation of idiosyncratic drug toxicity. Chem.-Biol. Interact. 142, 7-23.
    • (2002) Chem.-Biol. Interact. , vol.142 , pp. 7-23
    • Li, A.P.1
  • 7
    • 1642281756 scopus 로고    scopus 로고
    • Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development
    • Evans, D. C., Watt, A. P., Nicoll-Griffith, D. A., and Baillie, T. A. (2004) Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem. Res. Toxicol. 17, 3-16.
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 3-16
    • Evans, D.C.1    Watt, A.P.2    Nicoll-Griffith, D.A.3    Baillie, T.A.4
  • 8
    • 0035699746 scopus 로고    scopus 로고
    • Reactive metabolite screen for reducing candidate attrition in drug discovery
    • Chen, W. G., Zhang, C., Avery, M. J., and Fouda, H. G. (2001) Reactive metabolite screen for reducing candidate attrition in drug discovery. Adv. Exp. Med. Biol. 500, 521-524.
    • (2001) Adv. Exp. Med. Biol. , vol.500 , pp. 521-524
    • Chen, W.G.1    Zhang, C.2    Avery, M.J.3    Fouda, H.G.4
  • 9
    • 10044279528 scopus 로고    scopus 로고
    • Stable-isotope trapping and high-throughput screenings of reactive metabolites using the isotope MS signature
    • Yan, Z., and Caldwell, G. W. (2004) Stable-isotope trapping and high-throughput screenings of reactive metabolites using the isotope MS signature. Anal. Chem. 76, 6835-6847.
    • (2004) Anal. Chem. , vol.76 , pp. 6835-6847
    • Yan, Z.1    Caldwell, G.W.2
  • 10
    • 0027715770 scopus 로고
    • Specific targets of covalent drug-protein interactions in hepatocytes and their toxicological significance in drug-induced liver injury
    • Boelsterli, U. A. (1993) Specific targets of covalent drug-protein interactions in hepatocytes and their toxicological significance in drug-induced liver injury. Drug Metab. Rev. 25, 395-451.
    • (1993) Drug Metab. Rev. , vol.25 , pp. 395-451
    • Boelsterli, U.A.1
  • 11
  • 12
    • 0035200658 scopus 로고    scopus 로고
    • Cellular thiols and reactive oxygen species in drug-induced apoptosis
    • Davis, W., Jr., Ronai, Z. E., and Tew, K. D. (2001) Cellular Thiols and Reactive Oxygen Species in Drug-Induced Apoptosis. J. Pharmacol. Exp. Ther. 296, 1-6.
    • (2001) J. Pharmacol. Exp. Ther. , vol.296 , pp. 1-6
    • Davis Jr., W.1    Ronai, Z.E.2    Tew, K.D.3
  • 14
    • 0028805848 scopus 로고
    • Naphthylisothiocyanate disposition in bile and its relationship to liver glutathione and toxicity
    • Jean, P. A., and Roth, R. A. (1995) Naphthylisothiocyanate disposition in bile and its relationship to liver glutathione and toxicity. Biochem. Pharmacol. 50, 1469-1474.
    • (1995) Biochem. Pharmacol. , vol.50 , pp. 1469-1474
    • Jean, P.A.1    Roth, R.A.2
  • 15
    • 0021236594 scopus 로고
    • The metabolism and disposition of hexachloro-1:3-butadiene in the rat and its relevance to nephrotoxicity
    • Nash, J. A., King, L. J., Lock, E. A., and Green, T. (1984) The metabolism and disposition of hexachloro-1:3-butadiene in the rat and its relevance to nephrotoxicity. Toxicol. Appl. Pharmacol. 73, 124-137.
    • (1984) Toxicol. Appl. Pharmacol. , vol.73 , pp. 124-137
    • Nash, J.A.1    King, L.J.2    Lock, E.A.3    Green, T.4
  • 16
    • 0022724047 scopus 로고
    • Identification of S-1,2,2-trichlorovinyl-N-acetylcysteine as a urinary metabolite of tetrachloroethylene: Bioactivation through glutathione conjugation as a possible explanation of its nephrocarcinogenicity
    • Dekant, W., Metzler, M., and Henschler, D. (1986) Identification of S-1,2,2-trichlorovinyl-N-acetylcysteine as a urinary metabolite of tetrachloroethylene: Bioactivation through glutathione conjugation as a possible explanation of its nephrocarcinogenicity. J. Biochem. Toxicol. 1, 57-72.
    • (1986) J. Biochem. Toxicol. , vol.1 , pp. 57-72
    • Dekant, W.1    Metzler, M.2    Henschler, D.3
  • 18
    • 4444361038 scopus 로고    scopus 로고
    • The development of a higher throughput reactive intermediate screening assay incorporating micro-bore liquid chromatography-micro-electrospray ionization-tandem mass spectrometry and glutathione ethyl ester as an in vitro conjugating agent
    • Soglia, J. R., Harriman, S. P., Zhao, S., Barberia, J., Cole, M. J., Boyd, J. G., and Contillo, L. G. (2004) The development of a higher throughput reactive intermediate screening assay incorporating micro-bore liquid chromatography-micro-electrospray ionization-tandem mass spectrometry and glutathione ethyl ester as an in vitro conjugating agent. J. Pharm. Biomed. Anal. 36, 105-116.
    • (2004) J. Pharm. Biomed. Anal. , vol.36 , pp. 105-116
    • Soglia, J.R.1    Harriman, S.P.2    Zhao, S.3    Barberia, J.4    Cole, M.J.5    Boyd, J.G.6    Contillo, L.G.7
  • 19
    • 0028831731 scopus 로고
    • Quinone methide formation from para isomers of methylphenol (cresol), ethylphenol, and isopropylphenol: Relationship to toxicity
    • Thompson, D. C., Perera, K., and London, R. (1995) Quinone methide formation from para isomers of methylphenol (cresol), ethylphenol, and isopropylphenol: Relationship to toxicity. Chem. Res. Toxicol. 8, 55-60.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 55-60
    • Thompson, D.C.1    Perera, K.2    London, R.3
  • 20
    • 0032575366 scopus 로고    scopus 로고
    • Glutathione measurement in human plasma. Evaluation of sample collection, storage and derivatization conditions for analysis of dansyl derivatives by HPLC
    • Jones, D. P., Carlson, J. L., Samiec, P. S., Sternberg, P., Jr., Mody, V. C., Jr., Reed, R. L., and Brown, L. A. (1998) Glutathione measurement in human plasma. Evaluation of sample collection, storage and derivatization conditions for analysis of dansyl derivatives by HPLC. Clin. Chim. Acta 275, 175-184.
    • (1998) Clin. Chim. Acta , vol.275 , pp. 175-184
    • Jones, D.P.1    Carlson, J.L.2    Samiec, P.S.3    Sternberg Jr., P.4    Mody Jr., V.C.5    Reed, R.L.6    Brown, L.A.7
  • 21
    • 0034058752 scopus 로고    scopus 로고
    • Characterization of dansylated glutathione, glutathione disulfide, cysteine and cystine by narrow bore liquid chromatography/electrospray ionization mass spectrometry
    • Hammermeister, D. E., Serrano, J., Schmieder, P., and Kuehl, D. W. (2000) Characterization of dansylated glutathione, glutathione disulfide, cysteine and cystine by narrow bore liquid chromatography/electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 14, 503-508.
    • (2000) Rapid Commun. Mass Spectrom. , vol.14 , pp. 503-508
    • Hammermeister, D.E.1    Serrano, J.2    Schmieder, P.3    Kuehl, D.W.4
  • 22
    • 0029053262 scopus 로고
    • Mechanisms of the formation and disposition of reactive metabolites that can cause acute liver injury
    • Nelson, S. D. (1995) Mechanisms of the formation and disposition of reactive metabolites that can cause acute liver injury. Drug Metab. Rev. 27, 147-177.
    • (1995) Drug Metab. Rev. , vol.27 , pp. 147-177
    • Nelson, S.D.1
  • 23
    • 0032960136 scopus 로고    scopus 로고
    • Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: Evidence for formation of a furan epoxide
    • Khojasteh-Bakht, S. C., Chen, W., Koenigs, L. L., Peter, R. M., and Nelson, S. D. (1999) Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: Evidence for formation of a furan epoxide. Drug Metab. Dispos. 27, 574-580.
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 574-580
    • Khojasteh-Bakht, S.C.1    Chen, W.2    Koenigs, L.L.3    Peter, R.M.4    Nelson, S.D.5
  • 24
    • 0029416850 scopus 로고
    • The metabolic formation of reactive intermediates from clozapine, a drug associated with agranulocytosis in man
    • Maggs, J. L., Williams, D., Pirmohamed, M., and Park, B. K. (1995) The metabolic formation of reactive intermediates from clozapine, a drug associated with agranulocytosis in man. J. Pharmacol. Exp. Ther. 275, 1463-1475.
    • (1995) J. Pharmacol. Exp. Ther. , vol.275 , pp. 1463-1475
    • Maggs, J.L.1    Williams, D.2    Pirmohamed, M.3    Park, B.K.4
  • 25
    • 0029555342 scopus 로고
    • Clozapine is oxidized by activated human neutrophils to a reactive nitrenium ion that irreversibly binds to the cells
    • Liu, Z. C., and Uetrecht, J. P. (1995) Clozapine is oxidized by activated human neutrophils to a reactive nitrenium ion that irreversibly binds to the cells. J. Pharmacol. Exp. Ther. 275, 1476-1483.
    • (1995) J. Pharmacol. Exp. Ther. , vol.275 , pp. 1476-1483
    • Liu, Z.C.1    Uetrecht, J.P.2
  • 27
    • 17744394481 scopus 로고    scopus 로고
    • Studies on the metabolism of troglitazone to reactive intermediates in vitro and in vivo. Evidence for novel biotransformation pathways involving quinone methide formation and thiazolidinedione ring scission
    • Kassahun, K., Pearson, P. G., Tang, W., McIntosh, I., Leung, K., Elmore, C., Dean, D., Wang, R., Doss, G., and Baillie, T. A. (2001) Studies on the metabolism of troglitazone to reactive intermediates in vitro and in vivo. Evidence for novel biotransformation pathways involving quinone methide formation and thiazolidinedione ring scission. Chem. Res. Toxicol. 14, 62-70.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 62-70
    • Kassahun, K.1    Pearson, P.G.2    Tang, W.3    McIntosh, I.4    Leung, K.5    Elmore, C.6    Dean, D.7    Wang, R.8    Doss, G.9    Baillie, T.A.10
  • 28
    • 2442707819 scopus 로고    scopus 로고
    • Metabolic activation of troglitazone: Identification of a reactive metabolite and mechanisms involved
    • He, K., Talaat, R. E., Pool, W. F., Reily, M. D., Reed, J. E., Bridges, A. J., and Woolf, T. F. (2004) Metabolic activation of troglitazone: Identification of a reactive metabolite and mechanisms involved. Drug Metab. Dispos. 32, 639-646.
    • (2004) Drug Metab. Dispos. , vol.32 , pp. 639-646
    • He, K.1    Talaat, R.E.2    Pool, W.F.3    Reily, M.D.4    Reed, J.E.5    Bridges, A.J.6    Woolf, T.F.7
  • 29
    • 0034868665 scopus 로고    scopus 로고
    • Enzyme-induction dependent bioactivation of troglitazone and troglitazone quinone in vivo
    • Tettey, J. N., Maggs, J. L., Rapeport, W. G., Pirmohamed, M., and Park, B. K. (2001) Enzyme-induction dependent bioactivation of troglitazone and troglitazone quinone in vivo. Chem. Res. Toxicol. 14, 965-974.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 965-974
    • Tettey, J.N.1    Maggs, J.L.2    Rapeport, W.G.3    Pirmohamed, M.4    Park, B.K.5
  • 30
    • 0023878964 scopus 로고
    • Effects of chemical and enzymic probes on microsomal covalent binding of bromobenzene and derivatives. Evidence for quinones as reactive metabolites
    • Buben, J. A., Narasimhan, N., and Hanzlik, R. P. (1988) Effects of chemical and enzymic probes on microsomal covalent binding of bromobenzene and derivatives. Evidence for quinones as reactive metabolites. Xenobiotica 18, 501-510.
    • (1988) Xenobiotica , vol.18 , pp. 501-510
    • Buben, J.A.1    Narasimhan, N.2    Hanzlik, R.P.3
  • 31
    • 0026524152 scopus 로고
    • Bromobenzene-glutathione excretion into bile reflects toxic activation of bromobenzene in rats
    • Madhu, C., Klaassen, C. D., Buben, J. A., Narasimhan, N., and Hanzlik, R. P. (1992) Bromobenzene-glutathione excretion into bile reflects toxic activation of bromobenzene in rats. Toxicol. Lett. 60, 227-236.
    • (1992) Toxicol. Lett. , vol.60 , pp. 227-236
    • Madhu, C.1    Klaassen, C.D.2    Buben, J.A.3    Narasimhan, N.4    Hanzlik, R.P.5
  • 32
    • 0023097165 scopus 로고
    • Hepatotoxicity of precocene I in rats. Role of metabolic activation in vivo
    • Ravindranath, V., Boyd, M. R., and Jerina, D. M. (1987) Hepatotoxicity of precocene I in rats. Role of metabolic activation in vivo. Biochem. Pharmacol. 36, 441-446.
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 441-446
    • Ravindranath, V.1    Boyd, M.R.2    Jerina, D.M.3
  • 33
    • 0023916658 scopus 로고
    • Sequences, sequences, and sequences
    • Sanger, F. (1988) Sequences, sequences, and sequences. Ann. Rev. Biochem. 57, 1-29.
    • (1988) Ann. Rev. Biochem. , vol.57 , pp. 1-29
    • Sanger, F.1
  • 34
    • 0016275313 scopus 로고
    • Glutathione S-transferases. The first enzymatic step in mercapturic acid formation
    • Habig, W. H., Pabst, M. J., and Jakoby, W. B. (1974) Glutathione S-transferases. The first enzymatic step in mercapturic acid formation. J. Biol. Chem. 249, 7130-7139.
    • (1974) J. Biol. Chem. , vol.249 , pp. 7130-7139
    • Habig, W.H.1    Pabst, M.J.2    Jakoby, W.B.3
  • 35
    • 0036785479 scopus 로고    scopus 로고
    • Reactive intermediates and the dynamics of glutathione transferases
    • Rinaldi, R., Eliasson, E., Swedmark, S., and Morgenstern, R. (2002) Reactive intermediates and the dynamics of glutathione transferases. Drug Metab. Dispos. 30, 1053-1058.
    • (2002) Drug Metab. Dispos. , vol.30 , pp. 1053-1058
    • Rinaldi, R.1    Eliasson, E.2    Swedmark, S.3    Morgenstern, R.4
  • 36
    • 0031021397 scopus 로고    scopus 로고
    • Structure, catalytic mechanism, and evolution of the glutathione transferases
    • Armstrong, R. N. (1997) Structure, catalytic mechanism, and evolution of the glutathione transferases. Chem. Res. Toxicol. 10, 2-18.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 2-18
    • Armstrong, R.N.1
  • 37
    • 0031842867 scopus 로고    scopus 로고
    • A comparison of the oxidation of clozapine and olanzapine to reactive metabolites and the toxicity of these metabolites to human leukocytes
    • Gardner, I., Zahid, N., MacCrimmon, D., and Uetrecht, J. P. (1998) A comparison of the oxidation of clozapine and olanzapine to reactive metabolites and the toxicity of these metabolites to human leukocytes. Mol. Pharmacol. 53, 991-998.
    • (1998) Mol. Pharmacol. , vol.53 , pp. 991-998
    • Gardner, I.1    Zahid, N.2    MacCrimmon, D.3    Uetrecht, J.P.4
  • 39
    • 0038650658 scopus 로고    scopus 로고
    • Mechanisms of troglitazone hepatotoxicity
    • Smith, M. T. (2003) Mechanisms of troglitazone hepatotoxicity. Chem. Res. Toxicol. 16, 679-687.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 679-687
    • Smith, M.T.1
  • 40
    • 0037259315 scopus 로고    scopus 로고
    • Incidence of idiopathic acute liver failure and hospitalized liver injury in patients treated with troglitazone
    • Graham, D. J., Drinkard, C. R., and Shatin, D. (2003) Incidence of idiopathic acute liver failure and hospitalized liver injury in patients treated with troglitazone. Am. J. Gastroenterol. 98, 175-179.
    • (2003) Am. J. Gastroenterol. , vol.98 , pp. 175-179
    • Graham, D.J.1    Drinkard, C.R.2    Shatin, D.3
  • 41
    • 0142219774 scopus 로고    scopus 로고
    • Diclofenac-induced liver injury: A paradigm of idiosyncratic drug toxicity
    • Boelsterli, U. A. (2003) Diclofenac-induced liver injury: A paradigm of idiosyncratic drug toxicity. Toxicol. Appl. Pharmacol. 192, 307-322.
    • (2003) Toxicol. Appl. Pharmacol. , vol.192 , pp. 307-322
    • Boelsterli, U.A.1
  • 42
    • 0031770078 scopus 로고    scopus 로고
    • Examination of possible toxic and immune mechanisms of clozapine-induced agranulocytosis
    • Guest, I., Sokoluk, B., MacCrimmon, J., and Uetrecht, J. (1998) Examination of possible toxic and immune mechanisms of clozapine-induced agranulocytosis. Toxicology 131, 53-65.
    • (1998) Toxicology , vol.131 , pp. 53-65
    • Guest, I.1    Sokoluk, B.2    MacCrimmon, J.3    Uetrecht, J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.