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Volumn 41, Issue 11, 2011, Pages 964-971

The mechanism of enzymatic and non-enzymatic N-oxide reductive metabolism of cyadox in pig liver

Author keywords

Cyadox; Cyadox monoxide; N oxide reduction; N oxides; Non enzymatic reduction; Pigs

Indexed keywords

1 CYADOX MONOXIDE; 4 CYADOX MONOXIDE; ALDEHYDE OXIDASE; CATALASE; CIADOX; CYTOCHROME B5 REDUCTASE; CYTOCHROME P450; DRUG METABOLITE; FLAVINE ADENINE NUCLEOTIDE; HEME; HETEROCYCLIC COMPOUND; NITROGEN OXIDE; QUINOXALINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG; XANTHINE OXIDASE;

EID: 80053947167     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2011.593207     Document Type: Article
Times cited : (25)

References (34)
  • 1
    • 0029865395 scopus 로고    scopus 로고
    • 5 reductase
    • DOI 10.1016/0006-2952(95)02257-0
    • Barham HM, Stratford IJ. (1996). Enzymology of the reduction of the novel fused pyrazine mono-n-oxide bioreductive drug, RB90740 roles for P450 reductase and cytochrome b5 reductase. Biochem Pharmacol 51:829-837. (Pubitemid 26096294)
    • (1996) Biochemical Pharmacology , vol.51 , Issue.6 , pp. 829-837
    • Barham, H.M.1    Stratford, I.J.2
  • 2
    • 0014644925 scopus 로고
    • The pharmacology and biochemistry of N-oxides
    • Bickel MH. (1969). The pharmacology and biochemistry of N-oxides. Pharmacol Rev 21:325-355.
    • (1969) Pharmacol. Rev. , vol.21 , pp. 325-355
    • Bickel, M.H.1
  • 3
    • 0029566975 scopus 로고
    • Structure-activity relationship of coumarins in xanthine oxidase inhibition
    • Chang WS, Chiang HC. (1995). Structure-activity relationship of coumarins in xanthine oxidase inhibition. Anticancer Res 15:1969-1973.
    • (1995) Anticancer Res. , vol.15 , pp. 1969-1973
    • Chang, W.S.1    Chiang, H.C.2
  • 4
    • 33748577356 scopus 로고    scopus 로고
    • Effects of cyadox and olaquindox on intestinal mucosal immunity and on fecal shedding of Escherichia coli in piglets
    • DOI 10.2527/jas.2005-564
    • Ding MX, Wang YL, Zhu HL, Yuan ZH. (2006). Effects of cyadox and olaquindox on intestinal mucosal immunity and on fecal shedding of Escherichia coli in piglets. J Anim Sci 84:2367-2373. (Pubitemid 44367861)
    • (2006) Journal of Animal Science , vol.84 , Issue.9 , pp. 2367-2373
    • Ding, M.X.1    Wang, Y.L.2    Zhu, H.L.3    Yuan, Z.H.4
  • 5
    • 33646679840 scopus 로고    scopus 로고
    • Olaquindox and cyadox stimulate growth and decrease intestinal mucosal immunity of piglets orally inoculated with Escherichia coli
    • DOI 10.1111/j.1439-0396.2005.00593.x
    • Ding MX, Yuan ZH, Wang YL, Zhu HL, Fan SX. (2006). Olaquindox and cyadox stimulate growth and decrease intestinal mucosal immunity of piglets orally inoculated with Escherichia coli. J Anim Physiol Anim Nutr. 90:238-243. (Pubitemid 43742730)
    • (2006) Journal of Animal Physiology and Animal Nutrition , vol.90 , Issue.5-6 , pp. 238-243
    • Ding, M.X.1    Yuan, Z.H.2    Wang, Y.L.3    Zhu, H.L.4    Fan, S.X.5
  • 6
    • 28844458799 scopus 로고    scopus 로고
    • Subchronic oral toxicity study with cyadox in Wistar rats
    • DOI 10.1016/j.fct.2005.06.003, PII S0278691505001778
    • Fang G, He Q, Zhou S, Wang D, Zhang Y, Yuan Z. (2006). Subchronic oral toxicity study with cyadox in Wistar rats. Food Chem Toxicol 44:36-41. (Pubitemid 41773802)
    • (2006) Food and Chemical Toxicology , vol.44 , Issue.1 , pp. 36-41
    • Fang, G.1    He, Q.2    Zhou, S.3    Wang, D.4    Zhang, Y.5    Yuan, Z.6
  • 9
    • 53249089990 scopus 로고    scopus 로고
    • Development of high performance liquid chromatographic methods for the determination of cyadox and its metabolites in plasma and tissues of chicken
    • Huang L, Wang Y, Tao Y, Chen D, Yuan Z. (2008). Development of high performance liquid chromatographic methods for the determination of cyadox and its metabolites in plasma and tissues of chicken. J Chromatogr B 874:7-14.
    • (2008) J. Chromatogr. B. , vol.874 , pp. 7-14
    • Huang, L.1    Wang, Y.2    Tao, Y.3    Chen, D.4    Yuan, Z.5
  • 11
    • 0033005045 scopus 로고    scopus 로고
    • A unique tertiary amine N-oxide reduction system composed of quinone reductase and heme in rat liver preparations
    • Kitamura S, Sugihara K, Tatsumi K. (1999). A unique tertiary amine N-oxide reduction system composed of quinone reductase and heme in rat liver preparations. Drug Metab Dispos 27:92-97. (Pubitemid 29061006)
    • (1999) Drug Metabolism and Disposition , vol.27 , Issue.1 , pp. 92-97
    • Kitamura, S.1    Sugihara, K.2    Tatsumi, K.3
  • 12
    • 0021773411 scopus 로고
    • Involvement of liver aldehyde oxidase in the reduction of nicotinamide N-oxide
    • Kitamura S, Tatsumi K. (1984a). Involvement of liver aldehyde oxidase in the reduction of nicotinamide N-oxide. Biochem Biophys Res Commun 120:602-606.
    • (1984) Biochem. Biophys. Res. Commun. , vol.120 , pp. 602-606
    • Kitamura, S.1    Tatsumi, K.2
  • 13
    • 0021279818 scopus 로고
    • Reduction of tertiary amine N-oxides by liver preparations: Function of aldehyde oxidase and a major N-oxide reductase
    • Kitamura S, Tatsumi K. (1984b). Reduction of tertiary amine N-oxides by liver preparations: function of aldehyde oxidase as a major N-oxide reductase. Biochem Biophys Res Commun 121:749-754. (Pubitemid 14082243)
    • (1984) Biochemical and Biophysical Research Communications , vol.121 , Issue.3 , pp. 749-754
    • Kitamura, S.1    Tatsumi, K.2
  • 14
    • 67650360063 scopus 로고    scopus 로고
    • Metabolism of cyadox in rat chicken and pig liver microsomes and identification of metabolites by accurate mass measurements using electrospray ionization hybrid ion trap/time-of-flight mass spectrometry
    • Liu Z, Huang L, Dai M, Chen D, Tao Y, Wang Y, Yuan Z. (2009). Metabolism of cyadox in rat, chicken and pig liver microsomes and identification of metabolites by accurate mass measurements using electrospray ionization hybrid ion trap/time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 23:2026-2034.
    • (2009) Rapid. Commun. Mass. Spectrom. , vol.23 , pp. 2026-2034
    • Liu, Z.1    Huang, L.2    Dai, M.3    Chen, D.4    Tao, Y.5    Wang, Y.6    Yuan, Z.7
  • 15
    • 0014010958 scopus 로고
    • The reduction of nicotinamide N-oxide by xanthine oxidase
    • Murray KN, Chaykin S. (1966). The reduction of nicotinamide N-oxide by xanthine oxidase. J Biol Chem 241:3468-3473.
    • (1966) J. Biol. Chem. , vol.241 , pp. 3468-3473
    • Murray, K.N.1    Chaykin, S.2
  • 18
    • 4644297387 scopus 로고    scopus 로고
    • Kinetics and specificity of guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase towards substituted benzaldehydes
    • Panoutsopoulos GI, Beedham C. (2004). Kinetics and specificity of guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase towards substituted benzaldehydes. Acta Biochim Pol 51:649-663. (Pubitemid 39296919)
    • (2004) Acta Biochimica Polonica , vol.51 , Issue.3 , pp. 649-663
    • Panoutsopoulos, G.I.1    Beedham, C.2
  • 19
    • 0021266813 scopus 로고
    • Enzymatic and non-enzymatic reduction of n-acetyl-p-benzoquinone imine and some properties of the n-acetyl-p-benzosemiquinone imine radical
    • DOI 10.1016/0006-2952(84)90707-X
    • Powis G, Svingen BA, Dahlin DC, Nelson SD. (1984). Enzymatic and non-enzymatic reduction of N-acetyl-p-benzoquinone imine and some properties of the N-acetyl-p-benzosemiquinone imine radical. Biochem Pharmacol 33:2367-2370. (Pubitemid 14094610)
    • (1984) Biochemical Pharmacology , vol.33 , Issue.15 , pp. 2367-2370
    • Powis, G.1    Svingen, B.A.2    Dahlin, D.C.3    Nelson, S.D.4
  • 20
    • 0023639013 scopus 로고
    • Hydroxyurea, methotrexate and adriblastine can mediate non-enzymatic reduction of nitroblue tetrazolium with NADH which is inhibited by superoxide dismutase
    • DOI 10.1016/0006-2952(87)90652-6
    • Przybyszewski WM, Malec J. (1987). Hydroxyurea, methotrexate and adriblastine can mediate non-enzymatic reduction of nitroblue tetrazolium with NADH which is inhibited by superoxide dismutase. Biochem Pharmacol 36:3312-3314. (Pubitemid 17161024)
    • (1987) Biochemical Pharmacology , vol.36 , Issue.19 , pp. 3312-3314
    • Przybyszewski, W.M.1    Malec, J.2
  • 21
    • 0032717495 scopus 로고    scopus 로고
    • Rat cytochromes P450 CYP specifically contribute to the reductive bioactivation of AQ4N an alkylaminoanthraquinone-di-N-oxide anticancer prodrug
    • Raleigh SM, Wanogho E, Burke MD, Patterson LH. (1999). Rat cytochromes P450 (CYP) specifically contribute to the reductive bioactivation of AQ4N, an alkylaminoanthraquinone-di-N-oxide anticancer prodrug. Xenobiotica 29:1115-1122.
    • (1999) Xenobiotica , vol.29 , pp. 1115-1122
    • Raleigh, S.M.1    Wanogho, E.2    Burke, M.D.3    Patterson, L.H.4
  • 22
    • 0026502752 scopus 로고
    • Enzymology of the reduction of the potent benzotriazine-di-N-oxide hypoxic cell cytotoxin SR 4233 WIN 59075 by NAD P H: Quinone acceptor oxidoreductase EC 1.6.99.2 purified from Walker 256 rat tumour cells
    • Riley RJ, Workman P. (1992). Enzymology of the reduction of the potent benzotriazine-di-N-oxide hypoxic cell cytotoxin SR 4233 (WIN 59075) by NAD(P)H: (quinone acceptor) oxidoreductase (EC 1.6.99.2) purified from Walker 256 rat tumour cells. Biochem Pharmacol 43:167-174.
    • (1992) Biochem. Pharmacol. , vol.43 , pp. 167-174
    • Riley, R.J.1    Workman, P.2
  • 25
    • 0014670012 scopus 로고
    • Purine N-oxides 28 The reduction of purine N-oxides by xanthine oxidase
    • Stohrer G, Brown GB. (1969). Purine N-oxides. 28. The reduction of purine N-oxides by xanthine oxidase. J Biol Chem 244:2498-2502.
    • (1969) J. Biol. Chem. , vol.244 , pp. 2498-2502
    • Stohrer, G.1    Brown, G.B.2
  • 27
    • 0016246195 scopus 로고
    • Evidence for the involvement of cytochrome P-450 in tiaramide N-oxide reduction
    • Sugiura M, Iwasaki K, Noguchi H, Kato R. (1974). Evidence for the involvement of cytochrome P-450 in tiaramide N-oxide reduction. Life Sci 15:1433-1442.
    • (1974) Life. Sci. , vol.15 , pp. 1433-1442
    • Sugiura, M.1    Iwasaki, K.2    Noguchi, H.3    Kato, R.4
  • 28
    • 0035060888 scopus 로고    scopus 로고
    • Non-enzymatic reduction of aliphatic tertiary amine N-oxides mediated by the haem moiety of cytochrome P450
    • DOI 10.1080/00498250010024997
    • Takekawa K, Kitamura S, Sugihara K, Ohta S. (2001a). Non-enzymatic reduction of aliphatic tertiary amine N-oxides mediated by the haem moiety of cytochrome P450. Xenobiotica, 31: 11-23. (Pubitemid 32337058)
    • (2001) Xenobiotica , vol.31 , Issue.1 , pp. 11-23
    • Takekawa, K.1    Kitamura, S.2    Sugihara, K.3    Ohta, S.4
  • 29
    • 0035203609 scopus 로고    scopus 로고
    • Enzymatic and non-enzymatic reduction of brucine N-oxide by aldehyde oxidase and catalase
    • DOI 10.1080/00498250110065612
    • Takekawa K, Sugihara K, Kitamura S, Ohta S. (2001b). Enzymatic and non-enzymatic reduction of brucine N-oxide by aldehyde oxidase and catalase. Xenobiotica 31:769-782. (Pubitemid 33116450)
    • (2001) Xenobiotica , vol.31 , Issue.11 , pp. 769-782
    • Takekawa, K.1    Sugihara, K.2    Kitamura, S.3    Ohta, S.4
  • 31
    • 0026642263 scopus 로고
    • The role of cytochrome P450 and cytochrome P450 reductase in the reductive bioactivation of the novel benzotriazine di-N-oxide hypoxic cytotoxin 3-amino-1 2 4-benzotriazine-1 4-dioxide SR 4233 WIN 59075 by mouse liver
    • Walton MI, Wolf CR, Workman P. (1992). The role of cytochrome P450 and cytochrome P450 reductase in the reductive bioactivation of the novel benzotriazine di-N-oxide hypoxic cytotoxin 3-amino- 1,2,4-benzotriazine-1,4- dioxide (SR 4233, WIN 59075) by mouse liver. Biochem Pharmacol 44:251-259.
    • (1992) Biochem. Pharmacol. , vol.44 , pp. 251-259
    • Walton, M.I.1    Wolf, C.R.2    Workman, P.3
  • 33
    • 0019252569 scopus 로고
    • Stopped flow studies on the nonenzymatic reduction of methemoglobin by reduced flavin mononucleotide
    • Yubisui T, Matsukawa S, Yoneyama Y. (1980). Stopped flow studies on the nonenzymatic reduction of methemoglobin by reduced flavin mononucleotide. J Biol Chem 255:11694-11697. (Pubitemid 11132181)
    • (1980) Journal of Biological Chemistry , vol.255 , Issue.24 , pp. 11694-11697
    • Yubisui, T.1    Matsukawa, S.2    Yoneyama, Y.3


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