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Xenobiotica
the fate of foreign compounds in biological systems
Volume 34, 2004 - Issue 1
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Original Article

Oxidative one-carbon cleavage of the octyl side chain of olanexidine, a novel antimicrobial agent, in dog liver microsomes

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Pages 61-71 | Received 07 Jul 2003, Published online: 12 Jul 2010

Reference

  • AKHTAR, M., NJAR, V. C. 0. and WRIGHT, J. N., 1993, Mechanistic studies on aromatase and related C-C bond cleaving P-450 enzymes. Journal of Steroid Biochemistry and Molecular Biology, 44, 375–387.
  • BACK, D. J., TJIA, J. F., KARBWANG, J. and COLBERT, J., 1988, In vitro inhibition studies of tolbutamide hydroxylase activity of human liver microsomes by azoles, sulphonamides and quinolines. British Journal of Clinical Pharmacology, 26, 23–29.
  • BUENING, M. K. and FRANKLIN, M. R., 1974, The formation of complexes absorbing at 455 nm from cytochrome P-450 and metabolites of compounds related to SKF 525-A. Drug Metabolism and Disposition, 2, 386–390.
  • BYON, C. Y. and GUT, M., 1980, Steric considerations regarding the biodegradation of cholesterol to pregnenolone: exclusion of (22S)-22-hydroxycholesterol and 22-ketocholesterol as intermediates. Biochemical and Biophysical Research Communications, 94, 549–552.
  • CHAURET, N., GAUTHIER, A., MARTIN, J. and NICOLL-GRIFFITH, D. A., 1997, In vitro comparison of cytochrome P450-mediated metabolic activities in human, dog, cat, and horse. Drug Metabolism and Disposition, 25, 1130–1136.
  • COOK, C. S., BERRY, L. M., KIM, D. H., BURTON, E. G., HRIBAR, J. D. and ZHANG, L., 2002, Involvement of CYP3A in the metabolism of eplerenone in humans and dogs: differential metabolism by CYP3A4 and CYP3A5. Drug Metabolism and Disposition, 30, 1344–1351.
  • CORINA, D. L., MILLER, S. L., WRIGHT, J. N. and AKHTAR, M., 1991, The mechanism of cytochrome P-450 dependent C-C bond cleavage: studies on 17a-hydroxylase-17,20-lyase. Journal of the Chemical Society Chemical Communications, 782–783.
  • GUENGERICH, F. P., KIM, D. H. and IwAsAKI, M., 1991, Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chemical Research in Toxicology, 4, 168–179.
  • HARVEY, D. J., 1989, Further studies on the oxidative cleavage of the pentyl side-chain of cannabinoids: identification of new biotransformation pathways in the metabolism of 3'-hydroxy-delta-9-tetrahydrocannabinol by the mouse. Xenobiotica, 19, 1437–1447.
  • HARVEY, D. J., 1990, Oxidative cleavage of the pentyl side-chain of cannabinoids. Drug Metabolism and Disposition, 18, 350–355.
  • HARVEY, D. J. and LEUSCHNER, J. T. A., 1985, Studies on the 13-oxidative metabolism of Al- and Y-tetrahydrocannabinol in the mouse. Drug Metabolism and Disposition, 13, 215–219.
  • JANSEN, G. A., VAN DEN BRINK, D. M., OFMAN, R., DRAGHICI, 0., DACREMONT, G. and WANDERS, R. J., 2001, Identification of pristanal dehydrogenase activity in peroxisomes: conclusive evidence that the complete phytanic acid a-oxidation pathway is localized in peroxisomes. Biochemical and Biophysical Research Communications, 283, 674–679.
  • KOBAYASHI, S., MURRAY, S., WATSON, D., SESARDIC, D., DAVIES, D. S. and BOOBIS, A. R., 1989, The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine in the rat is the inverse of that in man. Biochemical Pharmacology, 38, 2795–2799.
  • KUDO, S., IWASAKI, M., SUGIMOTO, K., KODAMA, R. and ODOMI, M., 1998a, Absorption, distribution and excretion of OPB-2045 following a single subcutaneous administration to rats. Xenobiotic Metabolism and Disposition, 13, 1–7.
  • KUDO, S., IWASAKI, M., SUGIMOTO, K., KODAMA, R. and ODOMI, M., 1998b, Absorption, distribution and excretion of OPB-2045 following a single subcutaneous administration to beagle dogs. Xenobiotic Metabolism and Disposition, 13, 8–12.
  • KUDO, S., UMEHARA, K., MORITA, S., UCHIDA, M., MIYAMOTO, G. and ODOMI, M., 1998c, Metabolism of 1-(3,4-dichlorobenzy1)-5-octylbiguanide in the dog. Xenobiotica, 28, 507–514.
  • KUDO, S., UMEHARA, K., ODOMI, M. and MIYAMOTO, G., 1998d, Metabolism of a new bactericidal antiseptic, OPB-2045, in rats following subcutaneous administration. Xenobiotic Metabolism and Disposition, 13, 346–350.
  • Lu, A. Y. H., SOMOGYI, A., WEST, S., KUNTZMAN, R. and CONNEY, A. H., 1972, Pregnenolone-16a-carbonitrile: A new type of inducer of drug-metabolizing enzymes. Archives of Biochemistry and Biophysics, 125, 457–462.
  • MANNAERTS, G. P., VAN VELDHOVEN, P. P. and CASTEELS, M., 2000, Peroxisomal lipid-degradation via 13- and a-oxidation in mammals. Cell Biochemistry and Biophysics, 32, 73–87.
  • MILLER, S. L., WRIGHT, J. N., CORINA, D. L. and AKHTAR, M., 1991, Mechanistic studies on pregnene side-chain cleavage enzyme (17a-hydroxylase-17,20-lyase) using 180. Journal of the Chemical Society Chemical Communications, 157–159.
  • MINATO, K., Koizumi, N., HONMA, S., IWAMURA, S. and TsuKAmoTo, K., 1999, Characterizations of mouse hepatic microsomal monooxygenase catalyzing 11P-hydroxylation of osaterone acetate. Biochemical Pharmacology, 58, 335–341.
  • OHGURO, K., OHNISHI, H., TOMIGASHI, N., TSUBOUCHI, H. and KIKUCHI, M., 1997, Bactericidal activity of OPB-2045: a new antiseptic. Paper presented at the 20th International Congress of Chemotherapy, 29 June-3 July, Sydney, Australia.
  • ORTIZ DE MONTELLANO, P. R., 1995, Oxygen activation and reactivity. In P. R. Ortiz de Montellano (ed.), Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd edn (New York: Plenum), pp. 245–303.
  • OTTON, S. V., CREWE, H. K., LENNARD, M. S., TUCKER, G. T. and WOODS, H. F., 1988, Use of quinidine inhibition to define the role of the sparteine/debrisoquine cytochrome P450 in metoprolol oxidation by human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 247, 242–247.
  • ROUSSEL, F., DUIGNAN, D. B., LAWTON, M. P., OBACH, R. S., STRICK, C. A. and TWEEDIE, D. J., 1998, Expression and characterization of canine cytochrome P450 2D15. Archives of Biochemistry and Biophysics, 357, 27–36.
  • SAKAGAMI, Y., KAjimuEA, K. and NISHIMURA, H., 2000, Electron-microscopic study of the bactericidal effect of OPB-2045, a new disinfectant produced from biguanide group compounds, against methicillin-resistant Staphylococcus aureus. Journal of Pharmacy and Pharmacology, 52, 1547–1552.
  • SAKAGAMI, Y., MIMURA, M., KAJIMURA, K., YOKOYAMA, H. and NISHIMURA, H., 1999, Electron-microscopic study of the bactericidal effect of OPB-2045, a new mono-biguanide disinfectant produced from biguanide group compounds, against Pseudomonas aeruginosa. Journal of Pharmacy and Pharmacology, 51, 201–206.
  • SAMARA, E., BIALER, M., BAR-ON, H. and HARVEY, D. J., 1990, Identification of metabolites of the 1", 1"-dimethylheptyl analogue of cannabidiol in rat and dog in vivo. Xenobiotica, 20, 447–455.
  • SHIKITA, M. and HALL, P. F., 1974, The stoichiometry of the conversion of cholesterol and hydroxycholesterols to pregnenolone (33-hydroxypregn-5-en-20-one) catalysed by adrenal cytochrome P-450. Proceedings of the National Academy of Sciences, USA, 71, 1441–1445.
  • SMITH, D. A., 1991, Species differences in metabolism and pharmacokinetics: are we close to an understanding? Drug Metabolism Reviews, 23, 355–373.
  • SMITH, D. A. and JoNEs, B. C., 1992, Speculations on the substrate structure—activity relationship (SSAR) of cytochrome P450 enzymes. Biochemical Pharmacology, 44, 2089–2098.
  • SONDERFAN, A. J., ARLOTTO, M. P., DUTTON, D. R., MCMILLEN, S. K. and PARKINSON, A., 1987, Regulation of testosterone hydroxylation by rat liver microsomal cytochrome P-450. Archives of Biochemistry and Biophysics, 255, 27–41.
  • STROBL, G. and WOLFF, T., 1991, Molecular basis of drug metabolism interactions: a structural model for inhibitors of debrisoquine hydroxylase. Naunyn-Schmiedeberg's Archives of Pharmacology, 343(Suppl.), R8.
  • TAKAHASHI, T., TAKAHASHI, H., TAKEDA, H. and SHICHIRI, M., 1992, Alpha-oxidation of fatty acids in fasted or diabetic rats. Diabetes Research and Clinical Practice, 16, 103–108.
  • TASSANEEYAKUL, W., BIRKETT, D. J., VERONESE, M. E., McMANus, M. E., TUKEY, R. H., QUATTROCHI, L. C., GELBOIN, H. V. and MINERS, J. 0., 1993, Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. Journal of Pharmacology and Experimental Therapeutics, 265, 401–407.
  • TSUBOUCHI, H., OHGURO, K., YASUMURA, K., ISHIKAWA, H. and KIKUCHI, M., 1997, Synthesis and structure—activity relationships of novel antiseptics. Bioorganic and Medicinal Chemistry Letters, 7, 1721–1724.
  • UMEHARA, K., KUDO, S., HIRAO, Y., MORITA, S., OHTANI, T., UCHIDA, M. and MIYAMOTO, G., 2000b, In vitro characterization of the oxidative cleavage of the octyl side chain of olanexidine, a novel antimicrobial agent, in dog liver microsomes. Drug Metabolism and Disposition, 28, 1417–1424.
  • UMEHARA, K., KUDO, S., HIRAO, Y., MORITA, S., UCHIDA, M., ODOMI, M. and MIYAMOTO, G., 2000a, Oxidative cleavage of the octyl side chain of 1-(3,4-dichlorobenzy1)-5-octylbiguanide (OPB-2045) in rat and dog liver preparations. Drug Metabolism and Disposition, 28, 887–894.
  • VAMECQ, J. and DRAYE, J.-P., 1988, The enzymatic and mass spectrometric identification of 2-oxophytanic acid, a product of the peroxisomal oxidation of L-2-hydroxyphytanic acid. Biomedical and Environmental Mass Spectrometry, 15, 345–351.
  • VERHOEVEN, N. M., JAKOBS, C., CARNEY, G., SOMERS, M. P., WANDERS, R. J. and Rizzo, W. B., 1998, Involvement of microsomal fatty aldehyde dehydrogenase in the a-oxidation of phytanic acid. FEBS Letters, 429, 225–228.
  • WANDERS, R. J. A. and VAN ROERMUND, C. W. T., 1993, Studies on phytanic acid a-oxidation in rat liver and cultured human skin fibroblasts. Biochemica et Biophysica Acta, 1167, 345–350.
  • WATKINS, P. B., WRIGHTON, S. A., MAUREL, P., SCHUETZ, E. G., MENDEZ-PICON, G., PARKER, G. A. and GUZELIAN, P. S., 1985, Identification of an inducible form of cytochrome P-450 in human liver. Proceedings of the National Academy of Sciences, USA, 82, 6310–6314.
  • WRIGHTON, S. A., STEVENS, J. C., BECKER, G. W. and VANDENBRANDEN, M., 1993, Isolation and characterization of human liver cytochrome P450 2C19: correlation between 2C19 and S-mephenytoin 4'-hydroxylation. Archives of Biochemistry and Biophysics, 306, 240–245.

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