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Xenobiotica
the fate of foreign compounds in biological systems
Volume 43, 2013 - Issue 5
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General Xenobiochemistry

Interspecies variation in the metabolism of zoniporide by aldehyde oxidase

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Pages 399-408 | Received 14 Aug 2012, Accepted 03 Sep 2012, Published online: 10 Oct 2012

References

  • Akabane T, Tanaka K, Irie M, Terashita S, Teramura T. (2011). Case report of extensive metabolism by aldehyde oxidase in humans: pharmacokinetics and metabolite profile of FK3453 in rats, dogs, and humans. Xenobiotica 41:372–384.
  • Al-Salmy HS. (2001). Individual variation in hepatic aldehyde oxidase activity. IUBMB Life 51:249–253.
  • Al-Salmy HS. (2002). Inter-strain variability in aldehyde oxidase activity in the mouse. Comp Biochem Physiol C Toxicol Pharmacol 132:341–347.
  • Asakawa T, Itoh K, Adachi M, Hoshino K, Watanabe N, Tanaka Y. (2008). Properties of 130 kDa subunit of monkey aldehyde oxidase. Biol Pharm Bull 31:380–385.
  • Austin NE, Baldwin SJ, Cutler L, Deeks N, Kelly PJ, Nash M, Shardlow CE, Stemp G, Thewlis K, Ayrton A, Jeffrey P. (2001). Pharmacokinetics of the novel, high-affinity and selective dopamine D3 receptor antagonist SB-277011 in rat, dog and monkey: in vitro/in vivo correlation and the role of aldehyde oxidase. Xenobiotica 31:677–686.
  • Beedham C. (1987). Molybdenum hydroxylases: biological distribution and substrate-inhibitor specificity. Prog Med Chem 24:85–127.
  • Beedham C, al-Tayib Y, Smith JA. (1992). Role of guinea pig and rabbit hepatic aldehyde oxidase in oxidative in vitro metabolism of cinchona antimalarials. Drug Metab Dispos 20:889–895.
  • Beedham C, Bruce SE, Critchley DJ, al-Tayib Y, Rance DJ. (1987). Species variation in hepatic aldehyde oxidase activity. Eur J Drug Metab Pharmacokinet 12:307–310.
  • Beedham C, Bruce SE, Critchley DJ, Rance DJ. (1990). 1-substituted phthalazines as probes of the substrate-binding site of mammalian molybdenum hydroxylases. Biochem Pharmacol 39:1213–1221.
  • Beedham C, Critchley DJ, Rance DJ. (1995). Substrate specificity of human liver aldehyde oxidase toward substituted quinazolines and phthalazines: a comparison with hepatic enzyme from guinea pig, rabbit, and baboon. Arch Biochem Biophys 319:481–490.
  • Critchley DJ, Rance DJ, Beedham C. (1994). Biotransformation of carbazeran in guinea pig: effect of hydralazine pretreatment. Xenobiotica 24:37–47.
  • Dalvie D, Sun H, Xiang C, Hu Q, Jiang Y, Kang P. (2012). Effect of structural variation on aldehyde oxidase-catalyzed oxidation of zoniporide. Drug Metab Dispos 40:1575–1587.
  • Dalvie D, Zhang C, Chen W, Smolarek T, Obach RS, Loi CM. (2010). Cross-species comparison of the metabolism and excretion of zoniporide: contribution of aldehyde oxidase to interspecies differences. Drug Metab Dispos 38:641–654.
  • Diamond S, Boer J, Maduskuie TP Jr, Falahatpisheh N, Li Y, Yeleswaram S. (2010). Species-specific metabolism of SGX523 by aldehyde oxidase and the toxicological implications. Drug Metab Dispos 38:1277–1285.
  • Diaz GJ, Squires EJ. (2000). Role of aldehyde oxidase in the hepatic in vitro metabolism of 3-methylindole in pigs. J Agric Food Chem 48:833–837.
  • Fukiya K, Itoh K, Yamaguchi S, Kishiba A, Adachi M, Watanabe N, Tanaka Y. (2010). A single amino acid substitution confers high cinchonidine oxidation activity comparable with that of rabbit to monkey aldehyde oxidase 1. Drug Metab Dispos 38:302–307.
  • Garattini E, Fratelli M, Terao M. (2008). Mammalian aldehyde oxidases: genetics, evolution and biochemistry. Cell Mol Life Sci 65:1019–1048.
  • Garattini E, Fratelli M, Terao M. (2009). The mammalian aldehyde oxidase gene family. Hum Genomics 4:119–130.
  • Garattini E, Mendel R, Romão MJ, Wright R, Terao M. (2003). Mammalian molybdo-flavoenzymes, an expanding family of proteins: structure, genetics, regulation, function and pathophysiology. Biochem J 372:15–32.
  • Garattini E, Terao M. (2011). Increasing recognition of the importance of aldehyde oxidase in drug development and discovery. Drug Metab Rev 43:374–386.
  • Garattini E, Terao M. (2012). The role of aldehyde oxidase in drug metabolism. Expert Opin Drug Metab Toxicol 8:487–503.
  • Gluecksohn-Waelsch S, Greengard P, Quinn GP, Teicher LS. (1967). Genetic variations of an oxidase in mammals. J Biol Chem 242:1271–1273.
  • Guzman-Perez A, Wester RT, Allen MC, Brown JA, Buchholz AR, Cook ER, Day WW, Hamanaka ES, Kennedy SP, Knight DR, Kowalczyk PJ, Marala RB, Mularski CJ, Novomisle WA, Ruggeri RB, Tracey WR, Hill RJ. (2001). Discovery of zoniporide: a potent and selective sodium-hydrogen exchanger type 1 (NHE-1) inhibitor with high aqueous solubility. Bioorg Med Chem Lett 11:803–807.
  • Hoshino K, Itoh K, Masubuchi A, Adachi M, Asakawa T, Watanabe N, Kosaka T, Tanaka Y. (2007). Cloning, expression, and characterization of male cynomolgus monkey liver aldehyde oxidase. Biol Pharm Bull 30:1191–1198.
  • Hutzler JM, Yang YS, Albaugh D, Fullenwider CL, Schmenk J, Fisher MB. (2012). Characterization of aldehyde oxidase enzyme activity in cryopreserved human hepatocytes. Drug Metab Dispos 40:267–275.
  • Itoh K. (2009). [Individual and strain differences of aldehyde oxidase in the rat]. Yakugaku Zasshi 129:1487–1493.
  • Itoh K, Maruyama H, Adachi M, Hoshino K, Watanabe N, Tanaka Y. (2007a). Lack of dimer formation ability in rat strains with low aldehyde oxidase activity. Xenobiotica 37:709–716.
  • Itoh K, Maruyama H, Adachi M, Hoshino K, Watanabe N, Tanaka Y. (2007b). Lack of formation of aldehyde oxidase dimer possibly due to 377G>A nucleotide substitution. Drug Metab Dispos 35:1860–1864.
  • Itoh K, Yamamura M, Muramatsu S, Hoshino K, Masubuchi A, Sasaki T, Tanaka Y. (2005). Stereospecific oxidation of the (S)-enantiomer of RS-8359, a selective and reversible monoamine oxidase A (MAO-A) inhibitor, by aldehyde oxidase. Xenobiotica 35:561–573.
  • Itoh K, Yamamura M, Takasaki W, Sasaki T, Masubuchi A, Tanaka Y. (2006). Species differences in enantioselective 2-oxidations of RS-8359, a selective and reversible MAO-A inhibitor, and cinchona alkaloids by aldehyde oxidase. Biopharm Drug Dispos 27:133–139.
  • Jordan CG, Rashidi MR, Laljee H, Clarke SE, Brown JE, Beedham C. (1999). Aldehyde oxidase-catalysed oxidation of methotrexate in the liver of guinea-pig, rabbit and man. J Pharm Pharmacol 51:411–418.
  • Kawashima K, Hosoi K, Naruke T, Shiba T, Kitamura M, Watabe T. (1999). Aldehyde oxidase-dependent marked species difference in hepatic metabolism of the sedative-hypnotic, zaleplon, between monkeys and rats. Drug Metab Dispos 27:422–428.
  • Kaye B, Offerman JL, Reid JL, Elliott HL, Hillis WS. (1984). A species difference in the presystemic metabolism of carbazeran in dog and man. Xenobiotica 14:935–945.
  • Kaye B, Rance DJ, Waring L. (1985). Oxidative metabolism of carbazeran in vitro by liver cytosol of baboon and man. Xenobiotica 15:237–242.
  • Kitamura S, Nakatani K, Sugihara K, Ohta S. (1999a). Strain differences of the ability to hydroxylate methotrexate in rats. Comp Biochem Physiol C, Pharmacol Toxicol Endocrinol 122:331–336.
  • Kitamura S, Ohashi KNK, Sugihara K, Hosokawa R, Akagawa Y, Ohta S. (2001). Extremely high drug-reductase activity based on aldehyde oxidase in monkey liver. Biol Pharm Bull 24:856–859.
  • Kitamura S, Sugihara K, Nakatani K, Ohta S, Ohhara T, Ninomiya S, Green CE, Tyson CA. (1999b). Variation of hepatic methotrexate 7-hydroxylase activity in animals and humans. IUBMB Life 48:607–611.
  • Kitamura S, Sugihara K, Ohta S. (2006). Drug-metabolizing ability of molybdenum hydroxylases. Drug Metab Pharmacokinet 21:83–98.
  • Klecker RW, Cysyk RL, Collins JM. (2006). Zebularine metabolism by aldehyde oxidase in hepatic cytosol from humans, monkeys, dogs, rats, and mice: influence of sex and inhibitors. Bioorg Med Chem 14:62–66.
  • Knight DR, Smith AH, Flynn DM, MacAndrew JT, Ellery SS, Kong JX, Marala RB, Wester RT, Guzman-Perez A, Hill RJ, Magee WP, Tracey WR. (2001). A novel sodium-hydrogen exchanger isoform-1 inhibitor, zoniporide, reduces ischemic myocardial injury in vitro and in vivo. J Pharmacol Exp Ther 297:254–259.
  • Kunieda T, Kobayashi E, Tachibana M, Ikadai H. (1999). A genetic linkage map of rat chromosome 9 with a new locus for variant activity of liver aldehyde oxidase. Exp Anim 48:43–45.
  • Liu P, Liang S, Wang BJ, Guo RC. (2009). Construction of expression system of rabbit aldehyde oxidase cDNA for the clarification of species differences. Eur J Drug Metab Pharmacokinet 34:205–211.
  • Marala RB, Brown JA, Kong JX, Tracey WR, Knight DR, Wester RT, Sun D, Kennedy SP, Hamanaka ES, Ruggeri RB, Hill RJ. (2002). Zoniporide: a potent and highly selective inhibitor of human Na(+)/H(+) exchanger-1. Eur J Pharmacol 451:37–41.
  • Moriyasu A, Sugihara K, Nakatani K, Ohta S, Kitamura S. (2006). In vivo–in vitro relationship of methotrexate 7-hydroxylation by aldehyde oxidase in four different strain rats. Drug Metab Pharmacokinet 21:485–491.
  • O’Connor D, Jones P, Chambers MS, Maxey R, Szekeres HJ, Szeto N, Scott-Stevens P, Macleod AM, Braun M, Cato B. (2006). Aldehyde oxidase and its contribution to the metabolism of a structurally novel, functionally selective GABAA α5-subtype inverse agonist. Xenobiotica 36:315–330.
  • Pryde DC, Dalvie D, Hu Q, Jones P, Obach RS, Tran TD. (2010). Aldehyde oxidase: an enzyme of emerging importance in drug discovery. J Med Chem 53:8441–8460.
  • Rajagopalan KV, Handler P. (1966). Aldehyde oxidase. Methods Enzymol 9:364–368.
  • Rashidi MR, Smith JA, Clarke SE, Beedham C. (1997). In vitro oxidation of famciclovir and 6-deoxypenciclovir by aldehyde oxidase from human, guinea pig, rabbit, and rat liver. Drug Metab Dispos 25:805–813.
  • Rodrigues AD, Ferrero JL, Amann MT, Rotert GA, Cepa SP, Surber BW, Machinist JM, Tich NR, Sullivan JP, Garvey DS. (1994). The in vitro hepatic metabolism of ABT-418, a cholinergic channel activator, in rats, dogs, cynomolgus monkeys, and humans. Drug Metab Dispos 22:788–798.
  • Sahi J, Khan KK, Black CB. (2008). Aldehyde oxidase activity and inhibition in hepatocytes and cytosolic fractions from mouse, rat, monkey and human. Drug Metab Lett 2:176–183.
  • Sasaki T, Masubuchi A, Yamamura M, Watanabe N, Hiratsuka M, Mizugaki M, Itoh K, Tanaka Y. (2006). Rat strain differences in stereospecific 2-oxidation of RS-8359, a reversible and selective MAO-A inhibitor, by aldehyde oxidase. Biopharm Drug Dispos 27:247–255.
  • Schofield PC, Robertson IG, Paxton JW. (2000). Inter-species variation in the metabolism and inhibition of N-[(2’-dimethylamino)ethyl]acridine-4-carboxamide (DACA) by aldehyde oxidase. Biochem Pharmacol 59:161–165.
  • Schumann S, Terao M, Garattini E, Saggu M, Lendzian F, Hildebrandt P, Leimkühler S. (2009). Site directed mutagenesis of amino acid residues at the active site of mouse aldehyde oxidase AOX1. PLoS ONE 4:e5348.
  • Sugihara K, Kitamura S, Tatsumi K. (1995). Strain differences of liver aldehyde oxidase activity in rats. Biochem Mol Biol Int 37:861–869.
  • Takasaki W, Yamamura M, Nozaki A, Nitanai T, Sasahara K, Itoh K, Tanaka Y. (2005). Stereoselective pharmacokinetics of RS-8359, a selective and reversible MAO-A inhibitor, by species-dependent drug-metabolizing enzymes. Chirality 17:135–141.
  • Takasaki W, Yamamura M, Shigehara E, Suzuki Y, Tonohiro T, Hara T, Tanaka Y. (1999). Stereoselective pharmacokinetics of RS-8359, a selective and reversible inhibitor of A-type monoamine oxidase, in rats, mice, dogs, and monkeys. Biol Pharm Bull 22:498–503.
  • Terao M, Kurosaki M, Barzago MM, Varasano E, Boldetti A, Bastone A, Fratelli M, Garattini E. (2006). Avian and canine aldehyde oxidases. Novel insights into the biology and evolution of molybdo-flavoenzymes. J Biol Chem 281:19748–19761.
  • Tracey WR, Allen MC, Frazier DE, Fossa AA, Johnson CG, Marala RB, Knight DR, Guzman-Perez A. (2003). Zoniporide: a potent and selective inhibitor of the human sodium-hydrogen exchanger isoform 1 (NHE-1). Cardiovasc Drug Rev 21:17–32.
  • Wurzinger KH, Hartenstein R. (1974). Phylogeny and correlations of aldehyde oxidase, xanthine oxidase, xanthine dehydrogenase and peroxidase in animal tissues. Comp Biochem Physiol, B 49:171–185.
  • Yoshihara S, Tatsumi K. (1997). Involvement of growth hormone as a regulating factor in sex differences of mouse hepatic aldehyde oxidase. Biochem Pharmacol 53:1099–1105.
  • Zhang X, Liu HH, Weller P, Zheng M, Tao W, Wang J, Liao G, Monshouwer M, Peltz G. (2011). In silico and in vitro pharmacogenetics: aldehyde oxidase rapidly metabolizes a p38 kinase inhibitor. Pharmacogenomics J 11:15–24.
  • Zientek M, Jiang Y, Youdim K, Obach RS. (2010). In vitro–in vivo correlation for intrinsic clearance for drugs metabolized by human aldehyde oxidase. Drug Metab Dispos 38:1322–1327.

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