Evaluation of rhesus monkey and guinea pig hepatic cytosol fractions as models for human aldehyde oxidase

Drug Metabolism and Disposition

Volumn 41, Issue 10, 2013, Pages 1852-1858

  Choughule, Kanika V ^a   Barr, John T ^a   Jones, Jeffrey P ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE OXIDASE; ALDEHYDE OXIDASE ISOFORM 1; AMIDE; AMINO ACID; N [2 (DIMETHYLAMINO)ETHYL]ACRIDONE 4 CARBOXAMIDE; PHTHALAZINE DERIVATIVE; RALOXIFENE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOSOLIC FRACTION; DRUG CLEARANCE; DRUG OXIDATION; DRUG POTENCY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; ENZYME METABOLISM; FEMALE; GUINEA PIG MODEL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HUMAN TISSUE; IC 50; IN VITRO STUDY; LIPOPHILICITY; LIVER CYTOSOL; MALE; MICHAELIS MENTEN KINETICS; NONHUMAN; PRIORITY JOURNAL; RHESUS MONKEY; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY; SPECIES DIFFERENCE; TANDEM MASS SPECTROMETRY;

ALDEHYDE OXIDASE; ANIMALS; CYTOSOL; GUINEA PIGS; HUMANS; KINETICS; LIVER; MACACA MULATTA; MALE; OXIDATION-REDUCTION; PHTHALAZINES;

EID: 84884687953     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.113.052985     Document Type: Article

References (30)

1. Alfaro JF, Joswig-Jones CA, Ouyang W, Nichols J, Crouch GJ, and Jones JP (2009) Purification and mechanism of human aldehyde oxidase expressed in Escherichia coli. Drug Metab Dispos 37:2393-2398.
2. Austin NE, Baldwin SJ, Cutler L, Deeks N, Kelly PJ, Nash M, Shardlow CE, Stemp G, Thewlis K, and Ayrton A, et al. (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. (Pubitemid 32826399)
3. Barr JT and Jones JP (2011) Inhibition of human liver aldehyde oxidase: implications for potential drug-drug interactions. Drug Metab Dispos 39:2381-2386.
4. Barr JT and Jones JP (2013) Evidence for substrate-dependent inhibition profiles for human liver aldehyde oxidase. Drug Metab Dispos 41:24-29.
5. Beedham C, Bruce SE, Critchley DJ, al-Tayib Y, and Rance DJ (1987) Species variation in hepatic aldehyde oxidase activity. Eur J Drug Metab Pharmacokinet 12:307-310. (Pubitemid 18058717)
6. Beedham C, Critchley DJ, and 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.
7. Beedham C, Miceli JJ, and Obach RS (2003) Ziprasidone metabolism, aldehyde oxidase, and clinical implications. J Clin Psychopharmacol 23:229-232. (Pubitemid 36807789)
8. Coelho C, Mahro M, Trincão J, Carvalho AT, Ramos MJ, Terao M, Garattini E, Leimkühler S, and Romão MJ (2012) The first mammalian aldehyde oxidase crystal structure: insights into substrate specificity. J Biol Chem 287:40690-40702.
9. Dalvie D, Xiang C, Kang P, and Zhou S (2013) Interspecies variation in the metabolism of zoniporide by aldehyde oxidase. Xenobiotica 43:399-408.
10. Dittrich Ch, Greim G, Borner M, Weigang-Köhler K, Huisman H, Amelsberg A, Ehret A, Wanders J, Hanauske A, and Fumoleau P (2002) Phase I and pharmacokinetic study of BIBX 1382 BS, an epidermal growth factor receptor (EGFR) inhibitor, given in a continuous daily oral administration. Eur J Cancer 38:1072-1080. (Pubitemid 34468012)
11. Fukiya K, Itoh K, Yamaguchi S, Kishiba A, Adachi M, Watanabe N, and 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.
12. Garattini E, Mendel R, Romão MJ, Wright R, and Terao M (2003) Mammalian molybdoflavoenzymes, an expanding family of proteins: structure, genetics, regulation, function and pathophysiology. Biochem J 372:15-32. (Pubitemid 36609603)
13. Garattini E and Terao M (2012) The role of aldehyde oxidase in drug metabolism. Expert Opin Drug Metab Toxicol 8:487-503.
14. Garattini E and Terao M (2013) Aldehyde oxidase and its importance in novel drug discovery: present and future challenges. Expert Opin Drug Discov 8:641-654.
15. Hutzler JM, Obach RS, Dalvie D, and Zientek MA (2013) Strategies for a comprehensive understanding of metabolism by aldehyde oxidase. Expert Opin Drug Metab Toxicol 9:153-168.
16. Jones JP and Korzekwa KR (2013) Predicting intrinsic clearance for drugs and drug candidates metabolized by aldehyde oxidase. Mol Pharm 10:1262-1268.
17. Kitamura S, Sugihara K, and Ohta S (2006) Drug-metabolizing ability of molybdenum hydroxylases. Drug Metab Pharmacokinet 21:83-98.
18. Kollman P, McKelvey J, Johansson A, and Rothenberg S (1975) Theoretical studies of hydrogen-bonded dimers. Complexes involving HF, H2O, NH3, CH1, H2S, PH3, HCN, HNC, HCP, CH2NH, H2CS, H2CO, CH4, CF3,H, C2H2, C2H4, C6H6, F- and H3O+. J Am Chem Soc 97:955-965.
19. Morrison RD, Blobaum AL, Byers FW, Santomango TS, Bridges TM, Stec D, Brewer KA, Sanchez-Ponce R, Corlew MM, and Rush R, et al. (2012) The role of aldehyde oxidase and xanthine oxidase in the biotransformation of a novel negative allosteric modulator of metabotropic glutamate receptor subtype 5. Drug Metab Dispos 40:1834-1845.
20. Obach RS (2004) Potent inhibition of human liver aldehyde oxidase by raloxifene. Drug Metab Dispos 32:89-97.
21. Obach RS, Huynh P, Allen MC, and Beedham C (2004) Human liver aldehyde oxidase: inhibition by 239 drugs. J Clin Pharmacol 44:7-19. (Pubitemid 38005089)
22. Pryde DC, Dalvie D, Hu Q, Jones P, Obach RS, and Tran TD (2010) Aldehyde oxidase: an enzyme of emerging importance in drug discovery. J Med Chem 53:8441-8460.
23. Rashidi MR, Smith JA, Clarke SE, and 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. (Pubitemid 27318599)
24. Roberts AG, Yang J, Halpert JR, Nelson SD, Thummel KT, and Atkins WM (2011) The structural basis for homotropic and heterotropic cooperativity of midazolam metabolism by human cytochrome P450 3A4. Biochemistry 50:10804-10818.
25. Sahi J, Khan KK, and 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.
26. Schumann S, Terao M, Garattini E, Saggu M, Lendzian F, Hildebrandt P, and Leimkühler S (2009) Site directed mutagenesis of amino acid residues at the active site of mouse aldehyde oxidase AOX1. PLoS ONE 4:e5348.
27. Sharma R, Strelevitz TJ, Gao H, Clark AJ, Schildknegt K, Obach RS, Ripp SL, Spracklin DK, Tremaine LM, and Vaz AD (2012) Deuterium isotope effects on drug pharmacokinetics. I. System-dependent effects of specific deuteration with aldehyde oxidase cleared drugs. Drug Metab Dispos 40:625-634.
28. Shimoji M, Yin H, Higgins L, and Jones JP (1998) Design of a novel P450: a functional bacterial-human cytochrome P450 chimera. Biochemistry 37:8848-8852. (Pubitemid 28299652)
29. Takasaki W, Yamamura M, Nozaki A, Nitanai T, Sasahara K, Itoh K, and 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. (Pubitemid 40349519)
30. Torres RA, Korzekwa KR, McMasters DR, Fandozzi CM, and Jones JP (2007) Use of density functional calculations to predict the regioselectivity of drugs and molecules metabolized by aldehyde oxidase. J Med Chem 50:4642-4647. (Pubitemid 47463238)