메뉴 건너뛰기




Volumn 44, Issue 8, 2008, Pages 1645-1655

Redox cycling of 9,10-phenanthraquinone to cause oxidative stress is terminated through its monoglucuronide conjugation in human pulmonary epithelial A549 cells

Author keywords

9,10 Phenanthraquinone; Detoxification; Free radicals; Glucuronidation; Redox activity

Indexed keywords

5' DIPHOSPHATE GLUCURONOSYLTRANSFERASE; GLUCURONIDE; GLUCURONOSYLTRANSFERASE 1A10; GLUCURONOSYLTRANSFERASE 1A6; MONOGLUCURONIDE; PHENANTHRENEQUINONE; TRANSFERASE; UNCLASSIFIED DRUG;

EID: 41149155769     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2008.01.024     Document Type: Article
Times cited : (57)

References (37)
  • 1
    • 0030938017 scopus 로고    scopus 로고
    • Mechanisms of pollution-induced airway disease: in vivo studies
    • Peden D.B. Mechanisms of pollution-induced airway disease: in vivo studies. Allergy 52 (1997) 37-44
    • (1997) Allergy , vol.52 , pp. 37-44
    • Peden, D.B.1
  • 2
    • 0034886869 scopus 로고    scopus 로고
    • Potential mechanisms of adverse pulmonary and cardiovascular effects of particulate air pollution (PM10)
    • Donaldson K., and MacNee W. Potential mechanisms of adverse pulmonary and cardiovascular effects of particulate air pollution (PM10). Int. J. Hyg. Environ. Health 203 (2001) 411-415
    • (2001) Int. J. Hyg. Environ. Health , vol.203 , pp. 411-415
    • Donaldson, K.1    MacNee, W.2
  • 4
    • 14944377713 scopus 로고    scopus 로고
    • Increased oxidative stress in acute exacerbations of asthma
    • Nadeem A., Raj H.G., and Chhabra S.K. Increased oxidative stress in acute exacerbations of asthma. J. Asthma 42 (2005) 45-50
    • (2005) J. Asthma , vol.42 , pp. 45-50
    • Nadeem, A.1    Raj, H.G.2    Chhabra, S.K.3
  • 5
    • 0032101028 scopus 로고    scopus 로고
    • Engines and nanoparticles: a review
    • Kittelson D.B. Engines and nanoparticles: a review. J. Aerosol Sci. 29 (1998) 575-588
    • (1998) J. Aerosol Sci. , vol.29 , pp. 575-588
    • Kittelson, D.B.1
  • 7
    • 0020646229 scopus 로고
    • Sampling of vehicle emissions for chemical analysis and biological testing
    • Schuetzle D. Sampling of vehicle emissions for chemical analysis and biological testing. Environ. Health Perspect. 47 (1983) 65-80
    • (1983) Environ. Health Perspect. , vol.47 , pp. 65-80
    • Schuetzle, D.1
  • 8
    • 0036227531 scopus 로고    scopus 로고
    • Oxidation of proximal protein sulfhydryls by phenanthraquinone, a component of diesel exhaust particles
    • Kumagai Y., Koide S., Taguchi K., Endo A., Nakai Y., Yoshikawa T., and Shimojo N. Oxidation of proximal protein sulfhydryls by phenanthraquinone, a component of diesel exhaust particles. Chem. Res. Toxicol. 15 (2002) 483-489
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 483-489
    • Kumagai, Y.1    Koide, S.2    Taguchi, K.3    Endo, A.4    Nakai, Y.5    Yoshikawa, T.6    Shimojo, N.7
  • 9
    • 20644457548 scopus 로고    scopus 로고
    • The interactions of 9,10-phenanthrenequinone with glyceraldehyde-3-phosphate dehydrogenase (GAPDH), a potential site for toxic actions
    • Rodriguez C.E., Fukuto J.M., Taguchi K., Froines J., and Cho A.K. The interactions of 9,10-phenanthrenequinone with glyceraldehyde-3-phosphate dehydrogenase (GAPDH), a potential site for toxic actions. Chem. Biol. Interact. 155 (2005) 97-110
    • (2005) Chem. Biol. Interact. , vol.155 , pp. 97-110
    • Rodriguez, C.E.1    Fukuto, J.M.2    Taguchi, K.3    Froines, J.4    Cho, A.K.5
  • 10
    • 11344291782 scopus 로고    scopus 로고
    • 9,10-Phenanthraquinone in diesel exhaust particles downregulates Cu,Zn-SOD and HO-1 in human pulmonary epithelial cells: intracellular iron scavenger 1,10-phenanthroline affords protection against apoptosis
    • Sugimoto R., Kumagai Y., Nakai Y., and Ishii T. 9,10-Phenanthraquinone in diesel exhaust particles downregulates Cu,Zn-SOD and HO-1 in human pulmonary epithelial cells: intracellular iron scavenger 1,10-phenanthroline affords protection against apoptosis. Free Radic. Biol. Med. 38 (2005) 388-395
    • (2005) Free Radic. Biol. Med. , vol.38 , pp. 388-395
    • Sugimoto, R.1    Kumagai, Y.2    Nakai, Y.3    Ishii, T.4
  • 11
    • 0027200186 scopus 로고
    • Phototransformation of hydrophobic pollutants in aqueous medium. I. PAHs adsorbed on silica
    • David B., and Boule P. Phototransformation of hydrophobic pollutants in aqueous medium. I. PAHs adsorbed on silica. Chemosphere 26 (1993) 1617
    • (1993) Chemosphere , vol.26 , pp. 1617
    • David, B.1    Boule, P.2
  • 14
    • 0020464384 scopus 로고
    • DT-diaphorase as a quinone reductase: a cellular control device against semiquinone and superoxide radical formation
    • Lind C., Hochstein P., and Ernster L. DT-diaphorase as a quinone reductase: a cellular control device against semiquinone and superoxide radical formation. Arch. Biochem. Biophys. 216 (1982) 178-185
    • (1982) Arch. Biochem. Biophys. , vol.216 , pp. 178-185
    • Lind, C.1    Hochstein, P.2    Ernster, L.3
  • 15
    • 0024498044 scopus 로고
    • DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl-quinone conjugates: effect of substituents on autoxidation rates
    • Buffinton G.D., Ollinger K., Brunmark A., and Cadenas E. DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl-quinone conjugates: effect of substituents on autoxidation rates. Biochem. J. 257 (1989) 561-571
    • (1989) Biochem. J. , vol.257 , pp. 561-571
    • Buffinton, G.D.1    Ollinger, K.2    Brunmark, A.3    Cadenas, E.4
  • 16
    • 34547093431 scopus 로고    scopus 로고
    • An approach to evaluate two-electron reduction of 9,10-phenanthraquinone and redox activity of the hydroquinone associated with oxidative stress
    • Taguchi K., Fujii S., Cho A.K., Kamisuki S., Nakai Y., Yamano S., Sugawara F., Froines J.R., and Kumagai Y. An approach to evaluate two-electron reduction of 9,10-phenanthraquinone and redox activity of the hydroquinone associated with oxidative stress. Free Radic. Biol. Med. 43 (2007) 789-799
    • (2007) Free Radic. Biol. Med. , vol.43 , pp. 789-799
    • Taguchi, K.1    Fujii, S.2    Cho, A.K.3    Kamisuki, S.4    Nakai, Y.5    Yamano, S.6    Sugawara, F.7    Froines, J.R.8    Kumagai, Y.9
  • 17
    • 33344469643 scopus 로고    scopus 로고
    • Oxidative and electrophilic stresses activate Nrf2 through inhibition of ubiquitination activity of Keap1
    • Kobayashi A., Kang M.I., Watai Y., Tong K.I., Shibata T., Uchida K., and Yamamoto M. Oxidative and electrophilic stresses activate Nrf2 through inhibition of ubiquitination activity of Keap1. Mol. Cell. Biol. 26 (2006) 221-229
    • (2006) Mol. Cell. Biol. , vol.26 , pp. 221-229
    • Kobayashi, A.1    Kang, M.I.2    Watai, Y.3    Tong, K.I.4    Shibata, T.5    Uchida, K.6    Yamamoto, M.7
  • 21
    • 0029935829 scopus 로고    scopus 로고
    • Regulation of carbonyl-reducing enzymes in rat liver by chemoprotectors
    • Ellis E.M., Judah D.J., Neal G.E., O'Connor T., and Hayes J.D. Regulation of carbonyl-reducing enzymes in rat liver by chemoprotectors. Cancer Res. 56 (1996) 2758-2766
    • (1996) Cancer Res. , vol.56 , pp. 2758-2766
    • Ellis, E.M.1    Judah, D.J.2    Neal, G.E.3    O'Connor, T.4    Hayes, J.D.5
  • 22
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 23
    • 0031577312 scopus 로고    scopus 로고
    • Role of metabolic intermediates in lipopolysaccharide/cytokine-mediated production of nitric oxide in isolated mouse hepatocytes
    • Liang J.F., and Akaike T. Role of metabolic intermediates in lipopolysaccharide/cytokine-mediated production of nitric oxide in isolated mouse hepatocytes. Biochem. Biophys. Res. Commun. 236 (1997) 379-382
    • (1997) Biochem. Biophys. Res. Commun. , vol.236 , pp. 379-382
    • Liang, J.F.1    Akaike, T.2
  • 25
    • 0028291974 scopus 로고
    • Carbonyl assays for determination of oxidatively modified proteins
    • Levine R.L., Williams J.A., Stadtman E.R., and Shacter E. Carbonyl assays for determination of oxidatively modified proteins. Methods Enzymol. 233 (1994) 346-357
    • (1994) Methods Enzymol. , vol.233 , pp. 346-357
    • Levine, R.L.1    Williams, J.A.2    Stadtman, E.R.3    Shacter, E.4
  • 26
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays
    • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65 (1983) 55-63
    • (1983) J. Immunol. Methods , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 27
    • 0014428865 scopus 로고
    • Estimation of total, protein-bound, and nonprotein sulfhydryl groups in tissue with Ellman's reagent
    • Sedlak J., and Lindsay R.H. Estimation of total, protein-bound, and nonprotein sulfhydryl groups in tissue with Ellman's reagent. Anal. Biochem. 25 (1968) 192-205
    • (1968) Anal. Biochem. , vol.25 , pp. 192-205
    • Sedlak, J.1    Lindsay, R.H.2
  • 28
    • 0034128936 scopus 로고    scopus 로고
    • Human UDP-glucuronosyltransferases: metabolism, expression, and disease
    • Tukey R.H., and Strassburg C.P. Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu. Rev. Pharmacol. Toxicol. 40 (2000) 581-616
    • (2000) Annu. Rev. Pharmacol. Toxicol. , vol.40 , pp. 581-616
    • Tukey, R.H.1    Strassburg, C.P.2
  • 29
    • 33749008491 scopus 로고    scopus 로고
    • Simultaneous determination of urinary hydroxylated metabolites of naphthalene, fluorine, phenanthrene, fluoranthrene and pyrene as multiple biomarkers of exposure to polycyclic aromatic hydrocarbons
    • Chetiyanukornkul T., Toriba A., Kameda T., Tang N., and Hayakawa K. Simultaneous determination of urinary hydroxylated metabolites of naphthalene, fluorine, phenanthrene, fluoranthrene and pyrene as multiple biomarkers of exposure to polycyclic aromatic hydrocarbons. Anal. Bioanal. Chem. 386 (2006) 712-718
    • (2006) Anal. Bioanal. Chem. , vol.386 , pp. 712-718
    • Chetiyanukornkul, T.1    Toriba, A.2    Kameda, T.3    Tang, N.4    Hayakawa, K.5
  • 30
    • 32644442525 scopus 로고    scopus 로고
    • Assessment of soil workers' exposure to polycyclic aromatic hydrocarbons (PAH): biomonitoring of naphthols, phenanthrols, and 1-hydroxypyrene in urine
    • Elovaara E., Mikkola J., Makela M., Pakdanius B., and Priha E. Assessment of soil workers' exposure to polycyclic aromatic hydrocarbons (PAH): biomonitoring of naphthols, phenanthrols, and 1-hydroxypyrene in urine. Toxicol. Lett. 162 (2006) 158-163
    • (2006) Toxicol. Lett. , vol.162 , pp. 158-163
    • Elovaara, E.1    Mikkola, J.2    Makela, M.3    Pakdanius, B.4    Priha, E.5
  • 31
    • 0034819837 scopus 로고    scopus 로고
    • Protein engineering of Bacillus megaterium CYP102: the oxidation of polycyclic aromatic hydrocarbons
    • Carmichael A.B., and Wong L.L. Protein engineering of Bacillus megaterium CYP102: the oxidation of polycyclic aromatic hydrocarbons. Eur. J. Biochem. 268 (2001) 3117-3125
    • (2001) Eur. J. Biochem. , vol.268 , pp. 3117-3125
    • Carmichael, A.B.1    Wong, L.L.2
  • 34
    • 0028595707 scopus 로고
    • Use of cloned and expressed human liver UDP-glucuronosyltransferases for analysis of drug glucuronide formation and assessment of drug toxicity
    • Burchell B., Ebner T., Baird S., Bin Senafi S., Clarke D., Brierley C., and Sutherland L. Use of cloned and expressed human liver UDP-glucuronosyltransferases for analysis of drug glucuronide formation and assessment of drug toxicity. Environ. Health Perspect. 102 (1994) 19-23
    • (1994) Environ. Health Perspect. , vol.102 , pp. 19-23
    • Burchell, B.1    Ebner, T.2    Baird, S.3    Bin Senafi, S.4    Clarke, D.5    Brierley, C.6    Sutherland, L.7
  • 35
    • 0025871840 scopus 로고
    • Roles of UDP-glucuronosyltransferases in chemical carcinogenesis
    • Bock K.W. Roles of UDP-glucuronosyltransferases in chemical carcinogenesis. Crit. Rev. Biochem. Mol. Biol. 26 (1991) 129-150
    • (1991) Crit. Rev. Biochem. Mol. Biol. , vol.26 , pp. 129-150
    • Bock, K.W.1
  • 36
    • 0028070481 scopus 로고
    • Modulation of benzo[a]pyrene bioactivation by glucuronidation in lymphocytes and hepatic microsomes from rats with a hereditary deficiency in bilirubin UDP-glucuronosyltransferase
    • Hu Z., and Wells P.G. Modulation of benzo[a]pyrene bioactivation by glucuronidation in lymphocytes and hepatic microsomes from rats with a hereditary deficiency in bilirubin UDP-glucuronosyltransferase. Toxicol. Appl. Pharmacol. 127 (1994) 306-313
    • (1994) Toxicol. Appl. Pharmacol. , vol.127 , pp. 306-313
    • Hu, Z.1    Wells, P.G.2
  • 37
    • 0028956177 scopus 로고
    • Potential genoprotective role for UDP-glucuronosyltransferases in chemical carcinogenesis: initiation of micronuclei by benzo(a)pyrene and benzo(e)pyrene in UDP-glucuronosyltransferase-deficient cultured rat skin fibroblasts
    • Vienneau D.S., DeBoni U., and Wells P.G. Potential genoprotective role for UDP-glucuronosyltransferases in chemical carcinogenesis: initiation of micronuclei by benzo(a)pyrene and benzo(e)pyrene in UDP-glucuronosyltransferase-deficient cultured rat skin fibroblasts. Cancer Res. 55 (1995) 1045-1051
    • (1995) Cancer Res. , vol.55 , pp. 1045-1051
    • Vienneau, D.S.1    DeBoni, U.2    Wells, P.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.