Characterization of the binding of drugs to human intestinal fatty acid binding protein (IFABP): Potential role of IFABP as an alternative to albumin for in vitro-in vivo extrapolation of drug kinetic parameters

Drug Metabolism and Disposition

Volumn 37, Issue 7, 2009, Pages 1395-1403

  Rowland, Andrew ^a   Knights, Kathleen M ^a   Mackenzie, Peter I ^a   Miners, John O ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

8 ANILINO 1 NAPHTHALENESULFONIC ACID; ARACHIDONIC ACID; BOVINE SERUM ALBUMIN; CAFFEINE; DIAZEPAM; ESTRADIOL; FATTY ACID BINDING PROTEIN 2; FUROSEMIDE; LIDOCAINE; NAPROXEN; NORTRIPTYLINE; PHENYTOIN; PROPOFOL; PROPRANOLOL; SULFINPYRAZONE; TORASEMIDE; ZIDOVUDINE;

ADULT; AGED; ARTICLE; BINDING AFFINITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CLEARANCE; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG STRUCTURE; FEMALE; GLUCURONIDATION; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; IN VIVO STUDY; LIVER MICROSOME; MALE; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; WESTERN BLOTTING;

ALBUMINS; ANIMALS; ARACHIDONIC ACID; BINDING, COMPETITIVE; CATTLE; CELL LINE; CIRCULAR DICHROISM; FATTY ACID-BINDING PROTEINS; GLUCURONIDES; HUMANS; MUTAGENESIS, SITE-DIRECTED; PHENYTOIN; RECEPTORS, STEROID; SERUM ALBUMIN, BOVINE; SULFONAMIDES; THERMODYNAMICS; ZIDOVUDINE;

BOVINAE; RATTUS;

EID: 67649411647     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.109.027656     Document Type: Article

References (36)

1. Agellon LB, Toth MJ, and Thomson ABR (2002) Intracellular lipid binding proteins of the small intestine. Mol Cell Biochem 239:79-82. (Pubitemid 35385798)
2. Boase S and Miners JO (2002) In vitro-in vivo correlations for drugs eliminated by glucuronidation: investigation with the model substrate zidovudine. Br J Clin Pharmacol 54:493-503. (Pubitemid 35356875)
3. Bowalgaha K, Elliot DJ, Mackenzie PI, Knights KM, Swedmark S, and Miners JO (2005) Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br J Clin Pharmacol 60:423-433. (Pubitemid 41428474)
4. Brown HS, Griffin M, and Houston JB (2007) Evaluation of cryopreserved human hepatocytes as an alternative in vitro system to microsomes for the prediction of metabolic clearance. Drug Metab Dispos 35:293-301. (Pubitemid 46148743)
5. Chmurzyńska A (2006) The multi-gene family of fatty acid binding proteins (FABPs): function, structure and polymorphism. J Appl Genet 47:39-48. (Pubitemid 43232158)
6. Chuang S, Velkov T, Horne J, Porter CJ, and Scanlon MJ (2008) Characterization of the drug binding specificity of rat liver fatty acid binding protein. J Med Chem 51:3755-3764. (Pubitemid 351956507)
7. Engtrakul JJ, Foti RS, Strelevitz TJ, and Fisher MB (2005) Altered AZT (3′-azido-3′- deoxythymidine) glucuronidation kinetics in liver microsomes as an explanation for underprediction of in vivo clearance: comparison to hepatocytes and effect of incubation environment. Drug Metab Dispos 33:1621-1627. (Pubitemid 41539959)
8. Furuhashi M and Hotamisligil GS (2008) Fatty acid-binding proteins: role in metabolic diseases and potential as drug targets. Nat Rev Drug Discov 7:489-503. (Pubitemid 351767117)
9. Hamilton JA (2004) Fatty acid interactions with proteins: what X-ray crystal and NMR solution structures tell us. Prog Lipid Res 43:177-199. (Pubitemid 38299192)
10. Hodsdon ME and Cistola DP (1997) Ligand binding alters the backbone mobility of intestinal fatty acid-binding protein as monitored by 15N NMR relaxation and 1H exchange. Biochemistry 36:2278-2290. (Pubitemid 27104722)
11. Houston JB (1994) Utility of in vitro drug metabolism data in predicting in vivo metabolic clearance. Biochem Pharmacol 47:1469-1479. (Pubitemid 24167255)
12. Ito K and Houston JB (2005) Prediction of human drug clearance from in vitro and preclinical data using physiologically based and empirical approaches. Pharm Res 22:103-112. (Pubitemid 40558152)
13. Iwatsubo T, Hirota N, Ooie T, Suzuki H, Shimada N, Chiba K, Ishizaki T, Green CE, Tyson CA, and Sugiyama Y (1997) Prediction of in vivo drug metabolism in the human liver from in vitro metabolism data. Pharmacol Ther 73:147-171. (Pubitemid 27191615)
14. Johnson DL, Lewis BC, Elliot DJ, Miners JO, and Martin LL (2005) Electrochemical characterisation of the human cytochrome P450 CYP2C9. Biochem Pharmacol 69:1533-1541. (Pubitemid 40602454)
15. Kanda T, Ono T, Matsubara Y, and Muto T (1990) Possible role of fatty-acid binding protein in the intestine as carriers of phenol and phthalate derivatives. Biochem Biophys Res Commun 168:1053-1058. (Pubitemid 20175987)
16. Kerdpin O, Knights KM, Elliot DJ, and Miners JO (2008) In vitro characterisation of human renal and hepatic frusemide glucuronidation and identification of the UDP-glucuronosyltransferase enzymes involved in this pathway. Biochem Pharmacol 76:249-257.
17. Kirk WR, Kurian E, and Prendergast FG (1996) Characterization of the sources of protein-ligand affinity: 1-sulfonato-8-(1′) anilinonaphthalene binding to intestinal fatty acid binding protein. Biophys J 70:69-83. (Pubitemid 26021450)
18. Miners JO, Knights KM, Houston JB, and Mackenzie PI (2006) In vitro-in vivo correlation for drugs and other compounds eliminated by glucuronidation in humans: pitfalls and promises. Biochem Pharmacol 71:1531-1539.
19. Miners JO, Smith PA, Sorich MJ, McKinnon RA, and Mackenzie PI (2004) Predicting human drug glucuronidation parameters: applications of in vitro and in silico modelling approaches. Annu Rev Pharmacol Toxicol 44:1-25. (Pubitemid 38268090)
20. Moller M and Denicola A (2002) Study of protein-ligand binding by fluorescence. Biochem Mol Biol Edu 30:309-312. (Pubitemid 44132716)
21. Norris AW and Spector AA (2002) Very long chain n-3 and n-6 polyunsaturated fatty acids binding strongly to liver fatty acid-binding protein. J Lipid Res 43:646-653. (Pubitemid 34252340)
22. Obach RS, Baxter JG, Liston TE, Silber BM, Jones BC, MacIntyre F, Rance DJ, and Wastall P (1997) The prediction of human pharmacokinetic parameters from preclinical and in vitro metabolism data. J Pharmacol Exp Ther 283:46-58. (Pubitemid 27438945)
23. Richieri GV, Ogata RT, and Kleinfeld AM (1994) Equilibrium constants for the binding of fatty acids with fatty acid binding proteins from adipocyte, intestine, heart, and liver measured with a fluorescent probe ADIFAB. J Biol Chem 269:23918-23930. (Pubitemid 24300918)
24. Rowland A, Elliot DJ, Knights KM, Mackenzie PI, and Miners JO (2008a) The "albumin effect" and in vitro-in vivo extrapolation: sequestration of long-chain unsaturated fatty acids enhances phenytoin hydroxylation by human liver microsomal and recombinant cytochrome P450 2C9. Drug Metab Dispos 36:870-877. (Pubitemid 351574884)
25. Rowland A, Elliot DJ, Williams JA, Mackenzie PI, Dickinson RG, and Miners JO (2006) In vitro characterization of lamotrigine N2-glucuronidation and the lamotrigine-valproic acid interaction. Drug Metab Dispos 34:1055-1062. (Pubitemid 43763765)
26. Rowland A, Gaganis P, Elliot DJ, Mackenzie PI, Knights KM, and Miners JO (2007) Binding of inhibitory fatty acids is responsible for the enhancement of UDP glucuronosyltransferase 2B7 activity by albumin: implications for in vitro-in vivo extrapolation. J Pharmacol Exp Ther 321:137-147. (Pubitemid 46456976)
27. Rowland A, Knights KM, Mackenzie PI, and Miners JO (2008b) The "albumin effect" and drug glucuronidation: bovine serum albumin and fatty acid-free human serum albumin enhance the glucuronidation of UDP-glucuronosyltransferase (UGT) 1A9 substrates but not UGT1A1 and UGT1A6 activities. Drug Metab Dispos 36:1056-1062. (Pubitemid 351717462)
28. Sacchettini JC, Gordon JI, and Banaszak LJ (1989) Crystal structure of rat intestinal fatty acid binding protein. Refinement and analysis of the Escherichia coli derived protein with bound palmitate. J Mol Biol 208:327-339. (Pubitemid 19199909)
29. Tsoutsikos P, Miners JO, Stapleton A, Thomas A, Sallustio BC, and Knights KM (2004) Evidence that unsaturated fatty acids are potent inhibitors of renal UDP-glucuronosyltransferases (UGT): kinetic studies using human kidney cortical microsomes and recombinant UGT1A9 and UGT2B7. Biochem Pharmacol 67:191-199. (Pubitemid 37518547)
30. Uchaipichat V, Winner LK, Mackenzie PI, Elliot DJ, Williams JA, and Miners JO (2006) Quantitative prediction of in vivo inhibitory interactions involving glucuronidated drugs from in vitro data: the effect of fluconazole on zidovudine glucuronidation. Br J Clin Pharmacol 61:427-439.
31. Vassileva G, Huwyler L, Poirier K, Agellon LB, and Toth MJ (2000) The intestinal fatty acid binding protein is not essential for dietary fat absorption in mice. FASEB J 14:2040-2046. (Pubitemid 30747259)
32. Veerkamp JH and Maatman RG (1995) Cytoplasmic fatty acid binding proteins: their structure and genes. Prog Lipid Res 34:17-52.
33. Velkov T, Chuang S, Wielens J, Sakellaris H, Charman WN, Porter CJ, and Scanlon MJ (2005) The interaction of lipophilic drugs with intestinal fatty acid-binding protein. J Biol Chem 280:17769-17776. (Pubitemid 41389015)
34. Velkov T, Horne J, Laguerre A, Jones E, Scanlon MJ, and Porter CJ (2007) Examination of the role of intestinal fatty acid binding protein in drug absorption using a parallel artificial membrane permeability assay. Chem Biol 14:453-465. (Pubitemid 46617321)
35. Zhang F, Lücke C, Baier LJ, Sacchettini JC, and Hamilton JA (1997) Solution structure of human intestinal fatty acid binding protein: implications for ligand entry and exit. J Biomol NMR 9:213-228. (Pubitemid 127505384)
36. Zimmerman AW and Veerkamp JH (2002) New insights into the structure and function of fatty acid-binding proteins. Cell Mol Life Sci 59:1096-1116. (Pubitemid 34895405)