메뉴 건너뛰기




Volumn 18, Issue 5, 2005, Pages 880-888

Mechanistic studies on the metabolic scission of thiazolidinedione derivatives to acyclic thiols

Author keywords

[No Author keywords available]

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; 5 [(2,4 DIOXOTHIAZOLIDIN 5 YL)METHYL] 2 METHOXY N [[(4 TRIFLUOROMETHOXY)PHENYL]METHYL]BENZAMIDE; CUMENE HYDROPEROXIDE; CYTOCHROME P450; CYTOCHROME P450 3A4; DIMER; DISULFIDE; DRUG METABOLITE; GLUTATHIONE; MRL A; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; S ADENOSYLMETHIONINE; SULFENIC ACID DERIVATIVE; THIOL DERIVATIVE; TROGLITAZONE; UNCLASSIFIED DRUG;

EID: 18944394811     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0500373     Document Type: Article
Times cited : (29)

References (36)
  • 1
    • 0035124186 scopus 로고    scopus 로고
    • New oral therapies for type 2 diabetes mellitus: The glitazones or insulin sensitizers
    • Mudaliar, S., and Henry, R. R. (2001) New oral therapies for type 2 diabetes mellitus: The glitazones or insulin sensitizers. Annu. Rev. Med. 52, 239-257.
    • (2001) Annu. Rev. Med. , vol.52 , pp. 239-257
    • Mudaliar, S.1    Henry, R.R.2
  • 2
    • 0027980611 scopus 로고
    • Disposition and metabolism of the hypoglycemic agent pioglitazone in rats
    • Krieter, P. A., Colletti, A. E., Doss, G. A., and Miller, R. R. (1994) Disposition and metabolism of the hypoglycemic agent pioglitazone in rats. Drug Metab. Dispos. 22, 625-630.
    • (1994) Drug Metab. Dispos. , vol.22 , pp. 625-630
    • Krieter, P.A.1    Colletti, A.E.2    Doss, G.A.3    Miller, R.R.4
  • 5
    • 0029900481 scopus 로고    scopus 로고
    • The fate of a thiazolidinedione antidiabetic agent in rat and dog
    • Bolton, G. C., Keogh, J. P., East, P. D., Hollis, F. J., and Shore, A. D. (1996) The fate of a thiazolidinedione antidiabetic agent in rat and dog. Xenobiotica 26, 627-636.
    • (1996) Xenobiotica , vol.26 , pp. 627-636
    • Bolton, G.C.1    Keogh, J.P.2    East, P.D.3    Hollis, F.J.4    Shore, A.D.5
  • 7
    • 0032725398 scopus 로고    scopus 로고
    • Oxidation of troglitazone to a quinone-type metabolite catalyzed by cytochrome P-450 2C8 and P-450 3A4 in human liver microsomes
    • Yamazaki, H., Shibata, A., Suzuki, M., Nakajima, M., Shimada, N., Geungerich, F. P., and Yokoi, T. (1999) Oxidation of troglitazone to a quinone-type metabolite catalyzed by cytochrome P-450 2C8 and P-450 3A4 in human liver microsomes. Drug Metab. Dispos. 27, 1260-1266.
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 1260-1266
    • Yamazaki, H.1    Shibata, A.2    Suzuki, M.3    Nakajima, M.4    Shimada, N.5    Geungerich, F.P.6    Yokoi, T.7
  • 8
    • 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
  • 9
    • 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., Mclntosh, 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    Mclntosh, I.4    Leung, K.5    Elmore, C.6    Dean, D.7    Wang, R.8    Doss, G.9    Baillie, T.A.10
  • 11
    • 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
  • 12
    • 0033911580 scopus 로고    scopus 로고
    • Absorption, distribution, and metabolism of rosiglitazone, a potent thiazolidinedione insulin sensitizer, in humans
    • Cox, P. J., Ryan, D. A., Hollis, F. F., Harris, A. M., Miller, A. K., Vousden, M., and Cowley, H. (2000) Absorption, distribution, and metabolism of rosiglitazone, a potent thiazolidinedione insulin sensitizer, in humans. Drug Metab. Dispos. 28, 772-780.
    • (2000) Drug Metab. Dispos. , vol.28 , pp. 772-780
    • Cox, P.J.1    Ryan, D.A.2    Hollis, F.F.3    Harris, A.M.4    Miller, A.K.5    Vousden, M.6    Cowley, H.7
  • 13
    • 4143145642 scopus 로고    scopus 로고
    • In vitro metabolism of MK-0767, a peroxisome proliferator-activated receptor α/γ agonist. I. Role of cytochrome P450, methyltransferases, FMOs and esterases
    • Karanam, B. V., Hop, C. E. C. A., Liu, D., Mike, W., Dean, D., Toriumi, C., Domuro, M., Taga, F., Kusajima, H., and Vincent, S. H (2004) In vitro metabolism of MK-0767, a peroxisome proliferator-activated receptor α/γ agonist. I. Role of cytochrome P450, methyltransferases, FMOs and esterases. Drug Metab. Dispos. 32, 1015-1022.
    • (2004) Drug Metab. Dispos. , vol.32 , pp. 1015-1022
    • Karanam, B.V.1    Hop, C.E.C.A.2    Liu, D.3    Mike, W.4    Dean, D.5    Toriumi, C.6    Domuro, M.7    Taga, F.8    Kusajima, H.9    Vincent, S.H.10
  • 14
    • 4143061793 scopus 로고    scopus 로고
    • In vitro metabolism of MK-0767, a peroxisome proliferator-activated receptor α/γ agonist. II. Identification of metabolites by liquid chromatography-tandem mass spectrometry
    • Liu, D. Q., Karanam, B. V., Doss, G. A., Sidler, R. R., Vincent, S. H., and Hop, C. E. C. A. (2004) In vitro metabolism of MK-0767, a peroxisome proliferator-activated receptor α/γ agonist. II. Identification of metabolites by liquid chromatography-tandem mass spectrometry. Drug Metab. Dispos. 32, 1023-1031.
    • (2004) Drug Metab. Dispos. , vol.32 , pp. 1023-1031
    • Liu, D.Q.1    Karanam, B.V.2    Doss, G.A.3    Sidler, R.R.4    Vincent, S.H.5    Hop, C.E.C.A.6
  • 16
    • 0032125406 scopus 로고    scopus 로고
    • Two cases of severe clinical and histologic hepatotoxicity associated with troglitazone
    • Gitlin, N., Julie, N. L., Spurr, C. L., Lim, K. N., and Jurabe, H. M. (1998) Two cases of severe clinical and histologic hepatotoxicity associated with troglitazone. Ann. Intern. Med. 129, 38-41.
    • (1998) Ann. Intern. Med. , vol.129 , pp. 38-41
    • Gitlin, N.1    Julie, N.L.2    Spurr, C.L.3    Lim, K.N.4    Jurabe, H.M.5
  • 18
    • 0032568261 scopus 로고    scopus 로고
    • Hepatic dysfunction associated with troglitazone
    • Watkins, P. B., and Whitcomb, R. W. (1998) Hepatic dysfunction associated with troglitazone. N. Engl. J. Med. 338, 916-917.
    • (1998) N. Engl. J. Med. , vol.338 , pp. 916-917
    • Watkins, P.B.1    Whitcomb, R.W.2
  • 19
    • 18944365661 scopus 로고    scopus 로고
    • (2000) N-benzyldioxothiazolidylbenzamide derivatives and process for producing the same. U.S. Patent 6,030,990
    • Maeda, T., Nomura, M., Awano, K., Kinoshita, S., Satoh, H., Murakami, K., and Tsunoda, M. (2000) N-benzyldioxothiazolidylbenzamide derivatives and process for producing the same. U.S. Patent 6,030,990.
    • Maeda, T.1    Nomura, M.2    Awano, K.3    Kinoshita, S.4    Satoh, H.5    Murakami, K.6    Tsunoda, M.7
  • 20
    • 0035910579 scopus 로고    scopus 로고
    • A kinetic model for the metabolic interaction of two substrates at the active site of cytochrome P450 3A4
    • Shou, M., Dai, R., Cui, D., Korzekwa, K. R., Baillie, T. A., and Rushmore, T. H. (2001) A kinetic model for the metabolic interaction of two substrates at the active site of cytochrome P450 3A4. J. Biol. Chem. 276, 2256-2262.
    • (2001) J. Biol. Chem. , vol.276 , pp. 2256-2262
    • Shou, M.1    Dai, R.2    Cui, D.3    Korzekwa, K.R.4    Baillie, T.A.5    Rushmore, T.H.6
  • 21
    • 0029010216 scopus 로고
    • cDNA-directed expression of human cytochrome P450 1A1 using baculovirus. Purification, dependency on NADPH-P450 oxidoreductase, and reconstitution of catalytic properties without purification
    • Buters, J. T., Shou, M., Hardwick, J. P., Korzekwa, K. R., and Gonzalez, F. J. (1995) cDNA-directed expression of human cytochrome P450 1A1 using baculovirus. Purification, dependency on NADPH-P450 oxidoreductase, and reconstitution of catalytic properties without purification. Drug Metab. Dispos. 23, 696-701.
    • (1995) Drug Metab. Dispos. , vol.23 , pp. 696-701
    • Buters, J.T.1    Shou, M.2    Hardwick, J.P.3    Korzekwa, K.R.4    Gonzalez, F.J.5
  • 22
    • 0024518203 scopus 로고
    • Structural analysis of the FMN binding domain of NADPH-cytochrome P-450 oxidoreductase by site-directed mutagenesis
    • Shen, A. L., Porter, T. D., Wilson, T. E., and Kasper, C. B. (1989) Structural analysis of the FMN binding domain of NADPH-cytochrome P-450 oxidoreductase by site-directed mutagenesis. J. Biol. Chem. 264, 7584-7589.
    • (1989) J. Biol. Chem. , vol.264 , pp. 7584-7589
    • Shen, A.L.1    Porter, T.D.2    Wilson, T.E.3    Kasper, C.B.4
  • 23
    • 0027205012 scopus 로고
    • Mass spectrometry in the analysis of glutathione conjugates
    • Baillie, T. A., and Davis, M. R. (1993) Mass spectrometry in the analysis of glutathione conjugates. Biol. Mass Spectrom. 22, 319-325.
    • (1993) Biol. Mass Spectrom. , vol.22 , pp. 319-325
    • Baillie, T.A.1    Davis, M.R.2
  • 24
    • 0011224447 scopus 로고
    • Fragmentation characteristics of glutathione conjugates activated by high-energy collisions
    • Murphy, C. M., Fenselau, C., and Gutierrez, P. L. (1992) Fragmentation characteristics of glutathione conjugates activated by high-energy collisions. J. Am. Soc. Mass Spectrom. 3, 815-822.
    • (1992) J. Am. Soc. Mass Spectrom. , vol.3 , pp. 815-822
    • Murphy, C.M.1    Fenselau, C.2    Gutierrez, P.L.3
  • 26
    • 0029852501 scopus 로고    scopus 로고
    • Thiophene sulfoxides as reactive intermediates: Formation upon microsomal oxidation of a 3-aroylthiophene and fate in the presence of nucleophiles in vitro and in vivo
    • Valadon, P., Dansete, P. M., Girault, J. P., Amar, C., and Mansuy, D. (1996) Thiophene sulfoxides as reactive intermediates: Formation upon microsomal oxidation of a 3-aroylthiophene and fate in the presence of nucleophiles in vitro and in vivo. Chem. Res. Toxicol. 9, 1403-1413.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 1403-1413
    • Valadon, P.1    Dansete, P.M.2    Girault, J.P.3    Amar, C.4    Mansuy, D.5
  • 27
    • 0025880860 scopus 로고
    • Formation of glutathionyl-spironolactone disulfide by rat liver cytochromes P450 or hog liver flavin-containing monooxygenases: A functional probe of two-electron oxidations of the thiosteroid?
    • Decker, C. J., Cashman, J. R., Sugiyama, K., Maltby, D., and Correia, M. A. (1991) Formation of glutathionyl-spironolactone disulfide by rat liver cytochromes P450 or hog liver flavin-containing monooxygenases: A functional probe of two-electron oxidations of the thiosteroid? Chem. Res. Toxicol. 4, 669-677.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 669-677
    • Decker, C.J.1    Cashman, J.R.2    Sugiyama, K.3    Maltby, D.4    Correia, M.A.5
  • 28
    • 0024397272 scopus 로고
    • Oxidative metabolism of spironolactone: Evidence for the involvement of electrophilic thiosteroid species in drug-mediated destruction of rat hepatic cytochrome P450
    • Decker, C. J., Rashed, M. S., Baillie, T. A., Maltby, D., and Correia, M. A. (1989) Oxidative metabolism of spironolactone: Evidence for the involvement of electrophilic thiosteroid species in drug-mediated destruction of rat hepatic cytochrome P450. Biochemistry 28, 5128-5136.
    • (1989) Biochemistry , vol.28 , pp. 5128-5136
    • Decker, C.J.1    Rashed, M.S.2    Baillie, T.A.3    Maltby, D.4    Correia, M.A.5
  • 29
    • 0017113579 scopus 로고
    • Studies on hydroperoxide-dependent substrate hydroxylation by purified liver microsomal cytochrome P450
    • Nordblom, G. D., White, R. E., and Coon, M. J. (1976) Studies on hydroperoxide-dependent substrate hydroxylation by purified liver microsomal cytochrome P450. Arch. Biochem. Biophys. 175, 524-533.
    • (1976) Arch. Biochem. Biophys. , vol.175 , pp. 524-533
    • Nordblom, G.D.1    White, R.E.2    Coon, M.J.3
  • 30
    • 0016291443 scopus 로고
    • Hydroperoxide catalyzed liver microsomal aromatic hydroxylation reaction involving cytochrome P450
    • Rahimtula, A. D., and O'Brien, P. J. (1974) Hydroperoxide catalyzed liver microsomal aromatic hydroxylation reaction involving cytochrome P450. Biochem. Biophys. Res. Commun. 60, 440-447.
    • (1974) Biochem. Biophys. Res. Commun. , vol.60 , pp. 440-447
    • Rahimtula, A.D.1    O'Brien, P.J.2
  • 31
    • 0016837241 scopus 로고
    • Sodium periodate, sodium chlorite, organic hydroperoxides, and hydrogen peroxide as hydroxylating agents in steroid hydroxylation reaction catalyzed by partially purified cytochrome P450
    • Hrycay, E. G., Gustafsson, J.-A., Ingelman-Sundberg, M., and Ernster, L. (1975) Sodium periodate, sodium chlorite, organic hydroperoxides, and hydrogen peroxide as hydroxylating agents in steroid hydroxylation reaction catalyzed by partially purified cytochrome P450. Biochem. Biophys. Res. Commun. 66, 209-216.
    • (1975) Biochem. Biophys. Res. Commun. , vol.66 , pp. 209-216
    • Hrycay, E.G.1    Gustafsson, J.-A.2    Ingelman-Sundberg, M.3    Ernster, L.4
  • 32
    • 0015147501 scopus 로고
    • Cytochrome P450 as a microsomal peroxidase utilizing a lipid peroxide substrate
    • Hrycay, E. G., and O'Brien, P. J. (1971) Cytochrome P450 as a microsomal peroxidase utilizing a lipid peroxide substrate. Arch. Biochem. Biophys. 147, 14-27.
    • (1971) Arch. Biochem. Biophys. , vol.147 , pp. 14-27
    • Hrycay, E.G.1    O'Brien, P.J.2
  • 33
    • 77956787912 scopus 로고
    • Mechanisms and reactivity of organic oxyacids of sulfur and their anhydrides
    • (Gold, V., Bethell, D., Eds.), Academic Press, New York
    • Kice, J. L. (1980) Mechanisms and reactivity of organic oxyacids of sulfur and their anhydrides. In Advances in Physical Organic Chemistry (Gold, V., Bethell, D., Eds.) Vol. 17, pp 65-181, Academic Press, New York.
    • (1980) Advances in Physical Organic Chemistry , vol.17 , pp. 65-181
    • Kice, J.L.1
  • 34
    • 0020627222 scopus 로고
    • Synthesis and pH-dependent stability of purine-6-sulfenic acid, a putative reactive metabolite of 6-thiopurine
    • Abraham, R. T., Benson, L. M., and Jardine, I. (1983) Synthesis and pH-dependent stability of purine-6-sulfenic acid, a putative reactive metabolite of 6-thiopurine. J. Med. Chem. 26, 1523-1526.
    • (1983) J. Med. Chem. , vol.26 , pp. 1523-1526
    • Abraham, R.T.1    Benson, L.M.2    Jardine, I.3
  • 35
    • 33847805414 scopus 로고
    • The chemistry of alkyl thiosulfinate esters. VII. Mechanistic studies and synthetic applications
    • Block, E., and O'Connor, J. (1974) The chemistry of alkyl thiosulfinate esters. VII. Mechanistic studies and synthetic applications. J. Am. Chem. Soc. 96, 3929-3944.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 3929-3944
    • Block, E.1    O'Connor, J.2
  • 36
    • 0042589991 scopus 로고
    • Thiation of nucleosides. III. Oxidation of 6-mercaptopurines
    • Doerr, I. L., Wempen, I., Clarke, D. A., and Fox, J. J. (1961) Thiation of nucleosides. III. Oxidation of 6-mercaptopurines. J. Org. Chem. 26, 3401-3409.
    • (1961) J. Org. Chem. , vol.26 , pp. 3401-3409
    • Doerr, I.L.1    Wempen, I.2    Clarke, D.A.3    Fox, J.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.