Paraoxonase 1 as a major bioactivating hydrolase for olmesartan medoxomil in human blood circulation: Molecular identification and contribution to plasma metabolism

Drug Metabolism and Disposition

Volumn 40, Issue 2, 2012, Pages 374-380

  Ishizuka, Tomoko ^a   Fujimori, Izumi ^a   Nishida, Atsuko ^a   Sakurai, Hidetaka ^a   Yoshigae, Yasushi ^a   Nakahara, Kaori ^a   Kurihara, Atsushi ^a   Ikeda, Toshihiko ^b   Izumi, Takashi ^a  

^a DAIICHI SANKYO CO   (Japan)

^b YOKOHAMA COLLEGE OF PHARMACY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALBUMIN; ARYLDIALKYLPHOSPHATASE 1; CALCIUM ION; HIGH DENSITY LIPOPROTEIN; IMMUNOGLOBULIN G; OLMESARTAN; RECOMBINANT PROTEIN;

AMINO TERMINAL SEQUENCE; ARTICLE; CIRCULATION; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG HYDROLYSIS; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME PURIFICATION; HUMAN; HUMAN CELL; PRIORITY JOURNAL; SERUM;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANGIOTENSIN II TYPE 2 RECEPTOR BLOCKERS; ANIMALS; ANTIHYPERTENSIVE AGENTS; ARYLDIALKYLPHOSPHATASE; CALCIUM; HUMANS; HYDROLYSIS; IMIDAZOLES; ISOENZYMES; KINETICS; LIPOPROTEINS, HDL; MUTANT PROTEINS; PLASMA; PRODRUGS; RECOMBINANT PROTEINS; SEQUENCE ANALYSIS, PROTEIN; SPECIES SPECIFICITY; SUBSTRATE SPECIFICITY; TETRAZOLES;

EID: 84856020408     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.041475     Document Type: Article

References (34)

1. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254.
2. Chrysant SG (2008) Amlodipine/ARB fixed-dose combinations for the treatment of hypertension: focus on amlodipine/olmesartan combination. Drugs Today (Barc) 44:443-453.
3. Connelly PW, Maguire GF, Picardo CM, Teiber JF, and Draganov D (2008) Development of an immunoblot assay with infrared fluorescence to quantify paraoxonase 1 in serum and plasma. J Lipid Res 49:245-250.
4. Costa LG, Cole TB, Jarvik GP, and Furlong CE (2003) Functional genomic of the paraoxonase (PON1) polymorphisms: effects on pesticide sensitivity, cardiovascular disease, and drug metabolism. Annu Rev Med 54:371-392. (Pubitemid 37386402)
5. Costa LG, McDonald BE, Murphy SD, Omenn GS, Richter RJ, Motulsky AG, and Furlong CE (1990) Serum paraoxonase and its influence on paraoxon and chlorpyrifos-oxon toxicity in rats. Toxicol Appl Pharmacol 103:66-76. (Pubitemid 20115985)
6. Ettmayer P, Amidon GL, Clement B, and Testa B (2004) Lessons learned from marketed and investigational prodrugs. J Med Chem 47:2393-2404. (Pubitemid 38580074)
7. Gaidukov L and Tawfik DS (2005) High affinity, stability, and lactonase activity of serum paraoxonase PON1 anchored on HDL with ApoA-I. Biochemistry 44:11843-11854. (Pubitemid 41262719)
8. Gan KN, Smolen A, Eckerson HW, and La Du BN (1991) Purification of human serum paraoxonase/arylesterase. Evidence for one esterase catalyzing both activities. Drug Metab Dispos 19:100-106.
9. Garin MC, James RW, Dussoix P, Blanché H, Passa P, Froguel P, and Ruiz J (1997) Paraoxonase polymorphism Met-Leu54 is associated with modified serum concentrations of the enzyme. A possible link between the paraoxonase gene and increased risk of cardiovascular disease in diabetes. J Clin Invest 99:62-66. (Pubitemid 27058295)
10. Ginsberg G, Neafsey P, Hattis D, Guyton KZ, Johns DO, and Sonawane B (2009) Genetic polymorphism in paraoxonase 1 (PON1): population distribution of PON1 activity. J Toxicol Environ Health B Crit Rev 12:473-507.
11. Harel M, Aharoni A, Gaidukov L, Brumshtein B, Khersonsky O, Meged R, Dvir H, Ravelli RB, McCarthy A, Toker L, et al. (2004) Structure and evolution of the serum paraoxonase family of detoxifying and anti-atherosclerotic enzymes. Nat Struct Mol Biol 11:412-419. (Pubitemid 38568944)
12. Havel RJ, Eder HA, and Bragdon JH (1955) The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum. J Clin Invest 34:1345-1353.
13. Hioki T, Fukami T, Nakajima M, and Yokoi T (2011) Human paraoxonase 1 is the enzyme responsible for pilocarpine hydrolysis. Drug Metab Dispos 39:1345-1352.
14. Ishizuka T, Fujimori I, Kato M, Noji-Sakikawa C, Saito M, Yoshigae Y, Kubota K, Kurihara A, Izumi T, Ikeda T, et al. (2010) Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine. J Biol Chem 285:11892-11902.
15. Kobayashi N, Fujimori I, Watanabe M, and Ikeda T (2000) Real-time monitoring of metabolic reactions by microdialysis in combination with tandem mass spectrometry: hydrolysis of CS-866 in vitro in human and rat plasma, livers, and small intestines. Anal Biochem 287: 272-278. (Pubitemid 32006236)
16. Kuo CL and La Du BN (1995) Comparison of purified human and rabbit serum paraoxonases. Drug Metab Dispos 23:935-944.
17. La Du BN, Adkins S, Kuo CL, and Lipsig D (1993) Studies on human serum paraoxonase/ arylesterase. Chem Biol Interact 87:25-34. (Pubitemid 23205359)
18. Laeis P, Puchler K, and Kirch W (2001) The pharmacokinetic and metabolic profile of olmesartan medoxomil limits the risk of clinically relevant drug interaction. J Hypertens Suppl 19:S21-S32. (Pubitemid 32587656)
19. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680-685.
20. Li B, Sedlacek M, Manoharan I, Boopathy R, Duysen EG, Masson P, and Lockridge O (2005) Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem Pharmacol 70:1673-1684. (Pubitemid 41540360)
21. Ma SF, Anraku M, Iwao Y, Yamasaki K, Kragh-Hansen U, Yamaotsu N, Hirono S, Ikeda T, and Otagiri M (2005) Hydrolysis of angiotensin II receptor blocker prodrug olmesartan medoxomil by human serum albumin and identification of its catalytic active sites. Drug Metab Dispos 33:1911-1919. (Pubitemid 41699755)
22. Mackness B, Durrington PN, and Mackness MI (1998a) Human serum paraoxonase. Gen Pharmacol 31:329-336. (Pubitemid 28398854)
23. Mackness MI, Mackness B, Durrington PN, Fogelman AM, Berliner J, Lusis AJ, Navab M, Shih D, and Fonarow GC (1998b) Paraoxonase and coronary heart disease. Curr Opin Lipidol 9:319-324. (Pubitemid 28403351)
24. Ram CV (2011) Olmesartan medoxomil, amlodipine besylate and hydrochlorothiazide triple combination for hypertension. Expert Rev Cardiovasc Ther 9:9-19.
25. Renault F, Carus T, Cléry-Barraud C, Elias M, Chabrière E, Masson P, and Rochu D (2010) Integrative analytical approach by capillary electrophoresis and kinetics under high pressure optimized for deciphering intrinsic and extrinsic cofactors that modulate activity and stability of human paraoxonase (PON1). J Chromatogr B Analyt Technol Biomed Life Sci 878:1346-1355.
26. Rochu D, Renault F, Cléry-Barraud C, Chabrière E, and Masson P (2007) Stability of highly purified human paraoxonase (PON1): association with human phosphate binding protein (HPBP) is essential for preserving its active conformation(s). Biochim Biophys Acta 1774: 874-883. (Pubitemid 46977840)
27. Rump LC and Sellin L (2010) Combination therapy for hypertension: focus on high-dose olmesartan medoxomil (40 mg) plus hydrochlorothiazide. Expert Opin Pharmacother 11:2231-2242.
28. Satoh T and Hosokawa M (2006) Structure, function and regulation of carboxylesterases. Chem Biol Interact 162:195-211. (Pubitemid 44402409)
29. Scott LJ and McCormack PL (2008) Olmesartan medoxomil: a review of its use in the management of hypertension. Drugs 68:1239-1272. (Pubitemid 351822113)
30. Sorenson RC, Bisgaier CL, Aviram M, Hsu C, Billecke S, and La Du BN (1999) Human serum paraoxonase/arylesterase's retained hydrophobic N-terminal leader sequence associates with HDLs by binding phospholipids: apolipoprotein A-I stabilizes activity. Arterioscler Thromb Vasc Biol 19:2214-2225. (Pubitemid 29422255)
31. Testa B (2004) Prodrug research: futile or fertile? Biochem Pharmacol 68:2097-2106.
32. Testa B and Mayer JM (2003) Hydrolysis in Drug and Prodrug Metabolism: Chemistry, Biochemistry, and Enzymology, 1st ed, Wiley-VCH, Zürich.
33. Tougou K, Nakamura A, Watanabe S, Okuyama Y, and Morino A (1998) Paraoxonase has a major role in the hydrolysis of prulifloxacin (NM441), a prodrug of a new antibacterial agent. Drug Metab Dispos 26:355-359. (Pubitemid 28201246)
34. Yang J, Jamei M, Yeo KR, Tucker GT, and Rostami-Hodjegan A (2007) Prediction of intestinal first-pass drug metabolism. Curr Drug Metab 8:676-684. (Pubitemid 47578116)