메뉴 건너뛰기




Volumn 147, Issue 2, 2004, Pages 173-184

Hepatocellular bioactivation and cytotoxicity of the synthetic endoperoxide antimalarial arteflene

Author keywords

3 (4,5 dimethylthiazol 2 yl) 2,5 diphenyltetrazolium bromide; Arteflene; Dimethyl sulphoxide; DMSO; Hepatocytes; High performance liquid chromatography; HPLC; IPRL; Isolated perfused rat liver; LC MS; Liquid chromatography mass spectrometry; MTT

Indexed keywords

8 HYDROXYARTEFLENE GLUCURONIDE; ANTIMALARIAL AGENT; ARTEFLENE; CARBON 14; DRUG METABOLITE; ENZYME; GLUCURONIDE; OXIDOREDUCTASE; RADICAL; TETRAZOLIUM; UNCLASSIFIED DRUG;

EID: 1542346130     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2003.12.005     Document Type: Article
Times cited : (13)

References (50)
  • 2
    • 0028170764 scopus 로고
    • Tolerability and pharmacokinetics of Ro 42-1611 (arteflene) in man
    • Weidekamm E., Dumont E., Jaquet C. Tolerability and pharmacokinetics of Ro 42-1611 (arteflene) in man. Trop. Med. Parasitol. 45:1994;278-283.
    • (1994) Trop. Med. Parasitol. , vol.45 , pp. 278-283
    • Weidekamm, E.1    Dumont, E.2    Jaquet, C.3
  • 3
    • 0037021405 scopus 로고    scopus 로고
    • Artemisinin: Mechanisms of action, resistance and toxicity
    • Meshnick S.R. Artemisinin: mechanisms of action, resistance and toxicity. Int. J. Parasitol. 32:2002;1655-1660.
    • (2002) Int. J. Parasitol. , vol.32 , pp. 1655-1660
    • Meshnick, S.R.1
  • 5
    • 0035906935 scopus 로고    scopus 로고
    • Characterization of the alkylation product of heme by the antimalarial drug artemisinin
    • Robert A., Cazelles J., Meunier B. Characterization of the alkylation product of heme by the antimalarial drug artemisinin. Angew. Chem. Int. Ed. 40:2001;1954-1957.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1954-1957
    • Robert, A.1    Cazelles, J.2    Meunier, B.3
  • 6
    • 0142232014 scopus 로고    scopus 로고
    • Probing the possible molecular origin of the highly selective toxicity of antimalarial peroxide qinghaosu (artemisinin)
    • Wu Y., Liu H.-H. Probing the possible molecular origin of the highly selective toxicity of antimalarial peroxide qinghaosu (artemisinin). Chem. Res. Toxicol. 16:2003;1202-1206.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 1202-1206
    • Wu, Y.1    Liu, H.-H.2
  • 9
    • 0030879988 scopus 로고    scopus 로고
    • The rat biliary metabolites of dihydroartemisinin, an antimalarial endoperoxide
    • Maggs J.L., Madden S., Bishop L.P., O'Neill P.M., Park B.K. The rat biliary metabolites of dihydroartemisinin, an antimalarial endoperoxide. Drug Metab. Dispos. 25:1997;1200-1204.
    • (1997) Drug Metab. Dispos. , vol.25 , pp. 1200-1204
    • Maggs, J.L.1    Madden, S.2    Bishop, L.P.3    O'Neill, P.M.4    Park, B.K.5
  • 10
    • 0032947034 scopus 로고    scopus 로고
    • The metabolism of the antimalarial endoperoxide Ro 42-1611 (arteflene) in the rat: Evidence for endoperoxide bioactivation
    • Bishop L.P.D., Maggs J.L., O'Neill P.M., Park B.K. The metabolism of the antimalarial endoperoxide Ro 42-1611 (arteflene) in the rat: evidence for endoperoxide bioactivation. J. Pharmacol. Exp. Ther. 289:1999;511-520.
    • (1999) J. Pharmacol. Exp. Ther. , vol.289 , pp. 511-520
    • Bishop, L.P.D.1    Maggs, J.L.2    O'Neill, P.M.3    Park, B.K.4
  • 11
    • 0033802634 scopus 로고    scopus 로고
    • In vitro and in vivo potentiation of artemisinin and synthetic endoperoxide antimalarial drugs by metalloporphyrins
    • Benoit-Vical F., Robert A., Meunier B. In vitro and in vivo potentiation of artemisinin and synthetic endoperoxide antimalarial drugs by metalloporphyrins. Antimicrob. Agents Chemother. 44:2000;2836-2841.
    • (2000) Antimicrob. Agents Chemother. , vol.44 , pp. 2836-2841
    • Benoit-Vical, F.1    Robert, A.2    Meunier, B.3
  • 12
    • 0031722604 scopus 로고    scopus 로고
    • Safety assessment of peroxide antimalarials: Clinical and chemical perspectives
    • Park B.K., O'Neill P.M., Maggs J.L., Pirmohamed M. Safety assessment of peroxide antimalarials: clinical and chemical perspectives. Br. J. Clin. Pharmacol. 46:1998;521-529.
    • (1998) Br. J. Clin. Pharmacol. , vol.46 , pp. 521-529
    • Park, B.K.1    O'Neill, P.M.2    Maggs, J.L.3    Pirmohamed, M.4
  • 13
    • 0035855920 scopus 로고    scopus 로고
    • Antimalarial simplified 3-aryltrioxanes: Synthesis and preclinical efficacy toxicity testing in rodents
    • Posner G.H., Jeon H.B., Parker M.H., Krasavin M., Paik I.-H., Shapiro T.A. Antimalarial simplified 3-aryltrioxanes: synthesis and preclinical efficacy toxicity testing in rodents. J. Med. Chem. 44:2001;3054-3058.
    • (2001) J. Med. Chem. , vol.44 , pp. 3054-3058
    • Posner, G.H.1    Jeon, H.B.2    Parker, M.H.3    Krasavin, M.4    Paik, I.-H.5    Shapiro, T.A.6
  • 14
    • 0006899513 scopus 로고    scopus 로고
    • Safety of artemisinin and its derivatives: A review of published and unpublished clinical trials
    • Ribeiro I.R., Olliaro P. Safety of artemisinin and its derivatives: a review of published and unpublished clinical trials. Med. Trop. (Mars). 58:1998;50-53.
    • (1998) Med. Trop. (Mars) , vol.58 , pp. 50-53
    • Ribeiro, I.R.1    Olliaro, P.2
  • 16
    • 0032190142 scopus 로고    scopus 로고
    • Cytochrome P450 induction and cytotoxic effects of antimalarials in rat hepatocytes
    • Fontaine F., de Sousa G., Duchene P., Rahmani R. Cytochrome P450 induction and cytotoxic effects of antimalarials in rat hepatocytes. Toxicol. In Vitro. 12:1998;545-549.
    • (1998) Toxicol. in Vitro , vol.12 , pp. 545-549
    • Fontaine, F.1    De Sousa, G.2    Duchene, P.3    Rahmani, R.4
  • 17
    • 0025646009 scopus 로고
    • Metabolism of antimalarial sesquiterpene lactones
    • Lee I.-S., Hufford C.D. Metabolism of antimalarial sesquiterpene lactones. Pharmacol. Ther. 48:1990;345-355.
    • (1990) Pharmacol. Ther. , vol.48 , pp. 345-355
    • Lee, I.-S.1    Hufford, C.D.2
  • 18
    • 0032511205 scopus 로고    scopus 로고
    • Rapid characterization of artemether and its in vitro metabolites on incubation with bovine hemoglobin
    • Blum W., Pfaar U., Kuhnol J. Rapid characterization of artemether and its in vitro metabolites on incubation with bovine hemoglobin. J. Chromatogr. 710:1998;101-113.
    • (1998) J. Chromatogr. , vol.710 , pp. 101-113
    • Blum, W.1    Pfaar, U.2    Kuhnol, J.3
  • 19
    • 0030976258 scopus 로고    scopus 로고
    • The biomimetic iron-mediated degradation of arteflene (Ro-43-1611), an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity
    • O'Neill P.M., Bishop L.P., Searle N.L., Maggs J.L., Ward S.A., Bray P.G., Storr R.C., Park B.K. The biomimetic iron-mediated degradation of arteflene (Ro-43-1611), an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity. Tet. Lett. 38:1997;4263-4266.
    • (1997) Tet. Lett. , vol.38 , pp. 4263-4266
    • O'Neill, P.M.1    Bishop, L.P.2    Searle, N.L.3    Maggs, J.L.4    Ward, S.A.5    Bray, P.G.6    Storr, R.C.7    Park, B.K.8
  • 20
    • 0034629138 scopus 로고    scopus 로고
    • Biomimetic Fe(II)-mediated degradation of arteflene (Ro-42-1611). the first ESR spin-trapping evidence for the previously postulated secondary carbon-centered cyclohexyl radical
    • O'Neill P.M., Bishop L.P., Searle N.L., Maggs J.L., Storr R.C., Ward S.A., Park B.K., Mabbs F. Biomimetic Fe(II)-mediated degradation of arteflene (Ro-42-1611). The first ESR spin-trapping evidence for the previously postulated secondary carbon-centered cyclohexyl radical. J. Org. Chem. 65:2000;1578-1582.
    • (2000) J. Org. Chem. , vol.65 , pp. 1578-1582
    • O'Neill, P.M.1    Bishop, L.P.2    Searle, N.L.3    Maggs, J.L.4    Storr, R.C.5    Ward, S.A.6    Park, B.K.7    Mabbs, F.8
  • 22
    • 0031679973 scopus 로고    scopus 로고
    • Assessment of the effect of malaria infection on hepatic clearance of dihydroartemisinin using rat liver perfusions and microsomes
    • Batty K.T., Ilett K.F., Edwards G., Powell S.M., Maggs J.L., Park B.K., Davies T.M.E. Assessment of the effect of malaria infection on hepatic clearance of dihydroartemisinin using rat liver perfusions and microsomes. Br. J. Pharmacol. 125:1998;159-167.
    • (1998) Br. J. Pharmacol. , vol.125 , pp. 159-167
    • Batty, K.T.1    Ilett, K.F.2    Edwards, G.3    Powell, S.M.4    Maggs, J.L.5    Park, B.K.6    Davies, T.M.E.7
  • 24
    • 0022548996 scopus 로고
    • The isolated perfused rat liver: Conceptual and practical considerations
    • Gores G.J., Kost L.J., LaRusso N.F. The isolated perfused rat liver: conceptual and practical considerations. Hepatology. 6:1986;511-517.
    • (1986) Hepatology , vol.6 , pp. 511-517
    • Gores, G.J.1    Kost, L.J.2    Larusso, N.F.3
  • 25
    • 0032939943 scopus 로고    scopus 로고
    • Intracellular localization and metabolism of the phenanthridinium trypanocide, ethidium bromide, by isolated rat hepatocytes
    • Tettey J.N., Skellern G.G., Midgley J.M., Grant M.H., Wilkinson R., Pitt A.R. Intracellular localization and metabolism of the phenanthridinium trypanocide, ethidium bromide, by isolated rat hepatocytes. Xenobiotica. 29:1999;349-360.
    • (1999) Xenobiotica , vol.29 , pp. 349-360
    • Tettey, J.N.1    Skellern, G.G.2    Midgley, J.M.3    Grant, M.H.4    Wilkinson, R.5    Pitt, A.R.6
  • 26
    • 0022818865 scopus 로고
    • Methodologies for the application of monobromobimane to the simultaneous analysis of soluble and protein thiol components of biological systems
    • Cotgreave I.A., Moldeus P. Methodologies for the application of monobromobimane to the simultaneous analysis of soluble and protein thiol components of biological systems. J. Biochem. Biophys. Meth. 13:1986;231-249.
    • (1986) J. Biochem. Biophys. Meth. , vol.13 , pp. 231-249
    • Cotgreave, I.A.1    Moldeus, P.2
  • 27
    • 0031041266 scopus 로고    scopus 로고
    • Correlation of antimalarial activity of artemisinin with binding affinity with ferroprotoporphyrin IX
    • Paitayatat S., Tarnchompoo B., Thebtaranonth Y., Yuthavong Y. Correlation of antimalarial activity of artemisinin with binding affinity with ferroprotoporphyrin IX. J. Med. Chem. 40:1997;633-638.
    • (1997) J. Med. Chem. , vol.40 , pp. 633-638
    • Paitayatat, S.1    Tarnchompoo, B.2    Thebtaranonth, Y.3    Yuthavong, Y.4
  • 28
    • 0034088853 scopus 로고    scopus 로고
    • In situ localization and regulation of thromboxane a (2) synthase in normal and LPS-primed lungs
    • Ermert L., Ermert M., Duncker H.R., Grimminger F., Seeger W. In situ localization and regulation of thromboxane A (2) synthase in normal and LPS-primed lungs. Am. J. Physiol. 278:2000;L744-L753.
    • (2000) Am. J. Physiol. , vol.278 , pp. 744-L753
    • Ermert, L.1    Ermert, M.2    Duncker, H.R.3    Grimminger, F.4    Seeger, W.5
  • 30
    • 0027995192 scopus 로고
    • Prostacyclin and thromboxane synthase: New aspects of hemethiolate catalysis
    • Ullrich V., Brugger R. Prostacyclin and thromboxane synthase: new aspects of hemethiolate catalysis. Angew. Chem. Int. Ed. 33:1994;1911-1919.
    • (1994) Angew. Chem. Int. Ed. , vol.33 , pp. 1911-1919
    • Ullrich, V.1    Brugger, R.2
  • 31
    • 0031832805 scopus 로고    scopus 로고
    • Liver cell models in in vitro toxicology
    • Guillouzo A. Liver cell models in in vitro toxicology. Environ. Health Perspect. 106(Suppl. 2):1998;511-532.
    • (1998) Environ. Health Perspect. , vol.106 , Issue.SUPPL. 2 , pp. 511-532
    • Guillouzo, A.1
  • 33
    • 0024512810 scopus 로고
    • Thermospray mass spectroscopy/high performance liquid chromatographic identification of the metabolites formed from arteether using a rat liver microsome preparation
    • Baker J.K., Yarber R.H., Hufford C.D., Lee I.-S., ElSohly H.N., McChesney J.D. Thermospray mass spectroscopy/high performance liquid chromatographic identification of the metabolites formed from arteether using a rat liver microsome preparation. Biomed. Environ. Mass Spectrom. 18:1989;337-351.
    • (1989) Biomed. Environ. Mass Spectrom. , vol.18 , pp. 337-351
    • Baker, J.K.1    Yarber, R.H.2    Hufford, C.D.3    Lee, I.-S.4    Elsohly, H.N.5    McChesney, J.D.6
  • 34
    • 0030771582 scopus 로고    scopus 로고
    • Biomimetic metabolism of artelinic acid by chemical cytochrome P-450 model systems
    • Idowu O.R., Lin A.J., Grace J.M., Peggins J.O. Biomimetic metabolism of artelinic acid by chemical cytochrome P-450 model systems. Pharm. Res. 14:1997;1449-1454.
    • (1997) Pharm. Res. , vol.14 , pp. 1449-1454
    • Idowu, O.R.1    Lin, A.J.2    Grace, J.M.3    Peggins, J.O.4
  • 35
    • 0034697033 scopus 로고    scopus 로고
    • Xenobiotic-metabolizing cytochrome P450 convert prostaglandin endoperoxide to hydroxyheptadecatrienoic acid and the mutagen, malondialdehyde
    • Plastaras J.P., Guengerich F.P., Nebert D.W., Marnett L.J. Xenobiotic-metabolizing cytochrome P450 convert prostaglandin endoperoxide to hydroxyheptadecatrienoic acid and the mutagen, malondialdehyde. J. Biol. Chem. 275:2000;11784-11790.
    • (2000) J. Biol. Chem. , vol.275 , pp. 11784-11790
    • Plastaras, J.P.1    Guengerich, F.P.2    Nebert, D.W.3    Marnett, L.J.4
  • 36
    • 0034698139 scopus 로고    scopus 로고
    • Identification of CYP4F8 in human seminal vesicles as a prominent 19-hydroxylase of prostaglandin endoperoxides
    • Bylund J., Hidestrand M., Ingelman-Sundberg M., Oliw E.H. Identification of CYP4F8 in human seminal vesicles as a prominent 19-hydroxylase of prostaglandin endoperoxides. J. Biol. Chem. 275:2000;21844-21849.
    • (2000) J. Biol. Chem. , vol.275 , pp. 21844-21849
    • Bylund, J.1    Hidestrand, M.2    Ingelman-Sundberg, M.3    Oliw, E.H.4
  • 37
    • 0025824172 scopus 로고
    • Hepatic metabolism of artemisinin drugs. II. Metabolism of arteether in rat liver cytosol
    • Leskovac V., Theoharides A.D. Hepatic metabolism of artemisinin drugs. II. Metabolism of arteether in rat liver cytosol. Comp. Biochem. Physiol. 99C:1991;391-396.
    • (1991) Comp. Biochem. Physiol. , vol.99 , pp. 391-396
    • Leskovac, V.1    Theoharides, A.D.2
  • 39
    • 0027270211 scopus 로고
    • Characterization of the cellular reduction of 3-(4,5-dimethylthiazol-2- yl)-2,5-diphenyltetrazolium bromide (MTT): Subcellular localization, substrate dependence, and involvement of mitochondrial electron transport in MTT reduction
    • Berridge M.V., Tan A.S. Characterization of the cellular reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT): subcellular localization, substrate dependence, and involvement of mitochondrial electron transport in MTT reduction. Arch. Biochem. Biophys. 303:1993;474-482.
    • (1993) Arch. Biochem. Biophys. , vol.303 , pp. 474-482
    • Berridge, M.V.1    Tan, A.S.2
  • 40
    • 0029979290 scopus 로고    scopus 로고
    • Cytotoxicity of artemisinin, a dimer of dihydroartemisinin, artemisitene and eupatoriopicrin as evaluated by the MTT and clonogenic assay
    • Beekman A.C., Woerdenbag H.J., Kampinga H.H., Konings A.W.T. Cytotoxicity of artemisinin, a dimer of dihydroartemisinin, artemisitene and eupatoriopicrin as evaluated by the MTT and clonogenic assay. Phytother. Res. 10:1996;140-144.
    • (1996) Phytother. Res. , vol.10 , pp. 140-144
    • Beekman, A.C.1    Woerdenbag, H.J.2    Kampinga, H.H.3    Konings, A.W.T.4
  • 41
    • 0028181096 scopus 로고
    • α,β-Unsaturated carbonyl compounds: Inhibition of rat liver glutathione S-transferase isozymes and chemical reactions with reduced glutathione
    • Chien C., Kirollos K.S., Linderman R.J., Dauterman W.C. α,β-Unsaturated carbonyl compounds: inhibition of rat liver glutathione S-transferase isozymes and chemical reactions with reduced glutathione. Biochem. Biophys. Acta. 1204:1994;175-180.
    • (1994) Biochem. Biophys. Acta , vol.1204 , pp. 175-180
    • Chien, C.1    Kirollos, K.S.2    Linderman, R.J.3    Dauterman, W.C.4
  • 43
    • 0035400112 scopus 로고    scopus 로고
    • Thiyl radicals abstract hydrogen atoms from carbohydrates: Reactivity and selectivity
    • Pogocki D., Schöneich C. Thiyl radicals abstract hydrogen atoms from carbohydrates: reactivity and selectivity. Free Rad. Biol. Med. 31:2001;98-107.
    • (2001) Free Rad. Biol. Med. , vol.31 , pp. 98-107
    • Pogocki, D.1    Schöneich, C.2
  • 44
    • 0020789781 scopus 로고
    • Rate constants for the reactions of free radicals with oxygen in solution
    • Maillard B., Ingold K.U., Scaiano J.C. Rate constants for the reactions of free radicals with oxygen in solution. J. Am. Chem. Soc. 105:1983;5095-5099.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5095-5099
    • Maillard, B.1    Ingold, K.U.2    Scaiano, J.C.3
  • 45
    • 0032886808 scopus 로고    scopus 로고
    • Characterization of the main radical and products resulting from a reductive activation of the antimalarial arteflene (Ro 42-1611)
    • Cazelles J., Robert A., Meunier B. Characterization of the main radical and products resulting from a reductive activation of the antimalarial arteflene (Ro 42-1611). J. Org. Chem. 64:1999;6776-6781.
    • (1999) J. Org. Chem. , vol.64 , pp. 6776-6781
    • Cazelles, J.1    Robert, A.2    Meunier, B.3
  • 46
    • 0007758844 scopus 로고
    • Deuterio-isotope effect in the autoxidation of aralkyl hydrocarbons. Mechanism of the interaction of peroxy radicals
    • Russell G.A. Deuterio-isotope effect in the autoxidation of aralkyl hydrocarbons. Mechanism of the interaction of peroxy radicals. J. Am. Chem. Soc. 79:1957;3871-3877.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 3871-3877
    • Russell, G.A.1
  • 47
    • 0037174884 scopus 로고    scopus 로고
    • A comparative study on the hydroperoxide and thiol specificity of the glutathione peroxidase family and selenoprotein P
    • Takebe G., Yarimizu J., Saito Y., Hayashi T., Nakamura H., Yodoi J., Nagasawa S., Takahashi K. A comparative study on the hydroperoxide and thiol specificity of the glutathione peroxidase family and selenoprotein P. J. Biol. Chem. 277:2003;41254-41258.
    • (2003) J. Biol. Chem. , vol.277 , pp. 41254-41258
    • Takebe, G.1    Yarimizu, J.2    Saito, Y.3    Hayashi, T.4    Nakamura, H.5    Yodoi, J.6    Nagasawa, S.7    Takahashi, K.8
  • 48
    • 0038015010 scopus 로고    scopus 로고
    • Glutathione-thiyl radical scavenging and transferase properties of human glutaredoxin (thiotransferase)
    • Starke D.W., Chock P.B., Mieyal J.J. Glutathione-thiyl radical scavenging and transferase properties of human glutaredoxin (thiotransferase). J. Biol. Chem. 278:2003;14607-14613.
    • (2003) J. Biol. Chem. , vol.278 , pp. 14607-14613
    • Starke, D.W.1    Chock, P.B.2    Mieyal, J.J.3
  • 50
    • 0038440391 scopus 로고    scopus 로고
    • A short synthesis and biological evaluation of potent and nontoxic antimalarial bridged bicyclic β-sulfonyl-endoperoxides
    • Bachi M.D., Korshin E.E., Hoos R., Szpilman A.M., Ploypradith P., Xie S., Shapiro T.A., Posner G.H. A short synthesis and biological evaluation of potent and nontoxic antimalarial bridged bicyclic β-sulfonyl-endoperoxides. J. Med. Chem. 46:2003;2516-2533.
    • (2003) J. Med. Chem. , vol.46 , pp. 2516-2533
    • Bachi, M.D.1    Korshin, E.E.2    Hoos, R.3    Szpilman, A.M.4    Ploypradith, P.5    Xie, S.6    Shapiro, T.A.7    Posner, G.H.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.