Examination of the Role of Intestinal Fatty Acid-Binding Protein in Drug Absorption Using a Parallel Artificial Membrane Permeability Assay

Chemistry and Biology

Volumn 14, Issue 4, 2007, Pages 453-465

  Velkov, Tony ^a   Horne, James ^a   Laguerre, Aisha ^a   Jones, Eric ^a   Scanlon, Martin J ^a   Porter, Christopher J H ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

CHEMBIOL

Indexed keywords

DRUG; FATTY ACID BINDING PROTEIN; LIGAND;

ANIMAL; ARTICLE; ARTIFICIAL MEMBRANE; CHEMISTRY; INTESTINE ABSORPTION; INTESTINE CELL; METABOLISM; PERMEABILITY; PHARMACOKINETICS; RAT;

ANIMALS; ENTEROCYTES; FATTY ACID-BINDING PROTEINS; INTESTINAL ABSORPTION; LIGANDS; MEMBRANES, ARTIFICIAL; PERMEABILITY; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS; RATS;

EID: 34247232179     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2007.03.009     Document Type: Article

References (42)

1. Glatz J.F.C., Van der Vusse G.J., and Veerkamp J.H. Fatty acid binding proteins and their physiological significance. News Physiol. Sci. 35 (1988) 41-43
2. Hertzel A.V., and Bernlohr D.A. The mammalian fatty acid-binding protein multigene family: molecular and genetic insights into function. Trends Endocrinol. Metab. 5 (2000) 175-179
3. Paulussen R.J., Van Moerkerk H.T., and Veerkamp J.H. Immunochemical quantitation of fatty acid-binding proteins. Tissue distribution of liver and heart FABP types in human and porcine tissues. Int. J. Biochem. 22 (1990) 393-398
4. Bass N.M., and Manning J.A. Tissue expression of three structurally different fatty acid binding proteins from rat heart muscle, liver, and intestine. Biochem. Biophys. Res. Commun. 137 (1986) 929-935
5. Hodsdon M.E., and Cistola D.P. Discrete backbone disorder in the nuclear magnetic resonance structure of apo intestinal fatty acid-binding protein: implications for the mechanism of ligand entry. Biochemistry 36 (1997) 1450-1460
6. Zhang F., Lucke C., Baier L.J., Sacchettini J.C., and Hamilton J.A. Solution structure of human intestinal fatty acid binding protein: implications for ligand entry and exit. J. Biomol. NMR 9 (1997) 213-228
7. Zhang F., Lucke C., Baier L.J., Sacchettini J.C., and Hamilton J.A. Solution structure of human intestinal fatty acid binding protein with a naturally-occurring single amino acid substitution (A54T) that is associated with altered lipid metabolism. Biochemistry 42 (2003) 7339-7347
8. Thompson J., Winter N., Terwey D., Bratt J., and Banaszak L. The crystal structure of the liver fatty acid-binding protein. A complex with two bound oleates. J. Biol. Chem. 272 (1997) 7140-7150
9. Coe N.R., and Bernlohr D.A. Physiological properties and functions of intracellular fatty acid-binding proteins. Biochim. Biophys. Acta 1391 (1998) 287-306
10. Storch J., Veerkamp J.H., and Hsu K.T. Similar mechanisms of fatty acid transfer from human and rodent fatty acid-binding proteins to membranes: liver, intestine, heart muscle, and adipose tissue FABPs. Mol. Cell. Biochem. 239 (2002) 25-33
11. Velkov T., Chuang S., Wielens J., Sakellaris H., Charman W.N., Porter C.J., and Scanlon M.J. The interaction of lipophilic drugs with intestinal fatty acid-binding protein. J. Biol. Chem. 280 (2005) 17769-17776
12. Wolfrum C., Borrmann C.M., Borchers T., and Spener F. Fatty acids and hypolipidemic drugs regulate peroxisome proliferator-activated receptors α- and γ-mediated gene expression via liver fatty acid binding protein: a signaling path to the nucleus. Proc. Natl. Acad. Sci. USA 98 (2001) 2323-2328
13. Artursson P., Palm K., and Luthman K. Caco-2 monolayers in experimental and theoretical predictions of drug transport. Adv. Drug Deliv. Rev. 46 (2001) 27-43
14. Avdeef A. Drug Bioavailability: Estimation of Solubility, Permeability, Absorption and Bioavailability (2003), Wiley-VCH, Weinheim, Germany
15. Ito K., Suzuki H., Horie T., and Sugiyama Y. Apical/basolateral surface expression of drug transporters and its role in vectorial drug transport. Pharm. Res. 22 (2005) 1559-1577
16. Ory J.J., and Banaszak L.J. Studies of the ligand binding reaction of adipocyte lipid binding protein using the fluorescent probe 1, 8-anilinonaphthalene-8-sulfonate. Biophys. J. 77 (1999) 1107-1116
17. Hodsdon M.E., Ponder J.W., and Cistola D.P. The NMR solution structure of intestinal fatty acid-binding protein complexed with palmitate: application of a novel distance geometry algorithm. J. Mol. Biol. 264 (1996) 585-602
18. Grzesiek S., Bax A., Clore G.M., Gronenborn A.M., Hu J.S., Kaufman J., Palmer I., Stahl S.J., and Wingfield P.T. The solution structure of HIV-1 Nef reveals an unexpected fold and permits delineation of the binding surface for the SH3 domain of Hck tyrosine protein kinase. Nat. Struct. Biol. 3 (1996) 340-345
19. Sacchettini J.C., Gordon J.I., and Banaszak L.J. 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 (1989) 327-339
20. Peters Jr. T. All about Albumin: Biochemistry, Genetics, and Medical Applications (1996), Academic Press, San Diego
21. Ruell J.A., and Avdeef A. Absorption screening using the PAMPA approach. In: Yan Z., and Caldwell G.W. (Eds). Methods in Pharmacology and Toxicology Optimization in Drug Discovery: In Vitro Methods (2004), Humana Press, Totowa, NJ 36-87
22. Sawada G.A., Barsuhn C.L., Lutzke B.S., Houghton M.E., Padbury G.E., Ho N.F., and Raub T.J. Increased lipophilicity and subsequent cell partitioning decrease passive transcellular diffusion of novel, highly lipophilic antioxidants. J. Pharmacol. Exp. Ther. 288 (1999) 1317-1326
23. Lucke C., Gutiérrez-González L.H., and Hamilton J. Intracellular lipid binding proteins: evolution, structure and ligand binding. In: Duttaroy A.K., and Spener F. (Eds). Cellular Proteins and their Fatty Acids in Health and Disease (2003), Wiley-VCH, Weinheim, Germany 95-118
24. Sacchettini J.C., and Gordon J.I. Rat intestinal fatty acid binding protein. A model system for analyzing the forces that can bind fatty acids to proteins. J. Biol. Chem. 268 (1993) 18399-18402
25. Kirk W.R., Kurian E., and Prendergast F.G. Characterization of the sources of protein-ligand affinity: 1-sulfonato-8-(1′)anilinonaphthalene binding to intestinal fatty acid binding protein. Biophys. J. 70 (1996) 69-83
26. Fischer H., Gottschlich R., and Seelig A. Blood-brain barrier permeation: molecular parameters governing passive diffusion. J. Membr. Biol. 165 (1998) 201-211
27. Kampf J.P., Cupp D., and Kleinfeld A.M. Different mechanisms of free fatty acid flip-flop and dissociation revealed by temperature and molecular species dependence of transport across lipid vesicles. J. Biol. Chem. 281 (2006) 21566-21574
28. Guo W., Huang N., Cai J., Xie W., and Hamilton J.A. Fatty acid transport and metabolism in HepG2 cells. Am. J. Physiol. Gastrointest. Liver Physiol. 290 (2006) G528-G534
29. Weisiger R.A., and Zucker S.D. Transfer of fatty acids between intracellular membranes: roles of soluble binding proteins, distance, and time. Am. J. Physiol. Gastrointest. Liver Physiol. 282 (2002) G105-G115
30. Trotter P.J., and Storch J. Fatty acid uptake and metabolism in a human intestinal cell line (Caco-2): comparison of apical and basolateral incubation. J. Lipid Res. 32 (1991) 293-304
31. Luxon B.A., Milliano M.T., and Weisiger R.A. Induction of hepatic cytosolic fatty acid binding protein with clofibrate accelerates both membrane and cytoplasmic transport of palmitate. Biochim. Biophys. Acta 1487 (2000) 309-318
32. Adida A., and Spener F. Adipocyte-type fatty acid-binding protein as inter-compartmental shuttle for peroxisome proliferator activated receptor γ agonists in cultured cell. Biochim. Biophys. Acta 1761 (2006) 172-181
33. Synold T.W., Dussault I., and Forman B.M. The orphan nuclear receptor SXR coordinately regulates drug metabolism and transport. Nat. Med. 7 (2001) 584-590
34. Bagatolli L.A., Kivatinitz S.C., and Fidelio G.D. Interaction of small ligands with human serum albumin IIIA subdomain. How to determine the affinity constant using an easy steady state fluorescent method. J. Pharm. Sci. 85 (1996) 1131-1132
35. Grzesiek S., and Bax A. Improved 3D triple-resonance NMR techniques applied to a 31-kDa protein. J. Magn. Reson. 96 (1992) 432-440
36. Delaglio F., Grzesiek S., Vuister G.W., Zhu G., Pfeifer J., and Bax A. NMRPipe: a multidimensional spectral processing system based on UNIX pipes. J. Biolmol. NMR 6 (1995) 277-293
37. Goddard, T.D., and Kneller, D.G. (2006). SPARKY 3 (http://www.cgl.ucsf.edu/home/sparky).
38. Tugarinov V., and Kay L.E. Quantitative NMR studies of high molecular weight proteins: application to domain orientation and ligand binding in the 723 residue enzyme malate synthase G. J. Mol. Biol. 327 (2003) 1121-1133
39. Deprez C., Lloubes R., Gavioli M., Marion D., Guerlesquin F., and Blanchard L. Solution structure of the E. coli TolA C-terminal domain reveals conformational changes upon binding to the phage g3p N-terminal domain. J. Mol. Biol. 346 (2005) 1047-1057
40. DeLano W.L. PyMol (2002). http://www.pymol.org )
41. Rath N.P., Haq W., and Balendiran G.K. Fenofibric acid. Acta Crystallogr. C 61 (2005) o81-o84
42. Avdeef A. Absorption and Drug Development Solubility, Permeability, and Charge State (2003), Wiley-Interscience, Hoboken, NJ