Discovery of the Inhibitory Effect of a Phosphatidylinositol Derivative on P-Glycoprotein by Virtual Screening Followed by In Vitro Cellular Studies

PLoS ONE

Volumn 8, Issue 4, 2013, Pages

  Lucas, Xavier ^a   Simon, Silke ^a   Schubert, Rolf ^a   Günther, Stefan ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIMYRISTOYL SN GLYCERO 3 PHOSPHATE SODIUM SALT; INOSITOL DERIVATIVE; MULTIDRUG RESISTANCE PROTEIN; PHOSPHATIDIC ACID; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLETHANOLAMINE; PHOSPHATIDYLGLYCEROL; PHOSPHATIDYLINOSITOL (5) P1 1,2 DIHEXANOYL DISODIUM SALT; PHOSPHATIDYLINOSITOL 1,2 DIOCTANOYL SODIUM SALT; PHOSPHATIDYLSERINE; PHOSPHOLIPID; PROTEIN INHIBITOR; STEAROYL 2 OLEOYL SN GLYCERO 3 PHOSPHATE SODIUM SA;T; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL ASSAY; CELL STRAIN CACO 2; COMPUTER MODEL; CONTROLLED STUDY; CRYOELECTRON MICROSCOPY; HUMAN; HUMAN CELL; IN VITRO STUDY; LIGHT SCATTERING; MDCK CELL; MOLECULAR DOCKING; NONHUMAN; PROTEIN STRUCTURE; PROTEIN TRANSPORT; TRANSMISSION ELECTRON MICROSCOPY;

BIOLOGICAL TRANSPORT; CACO-2 CELLS; CELL LINE; CHEMISTRY, PHARMACEUTICAL; CRYOELECTRON MICROSCOPY; DIGOXIN; DRUG DISCOVERY; DRUG RESISTANCE, MULTIPLE; FLUORESCEINS; HUMANS; MOLECULAR DOCKING SIMULATION; P-GLYCOPROTEINS; PERMEABILITY; PHOSPHATIDYLINOSITOLS; PHOSPHOLIPIDS; PROTEIN BINDING; PROTEIN CONFORMATION;

EID: 84876066260     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0060679     Document Type: Article

References (43)

1. van Meer G, Voelker DR, Fei GW, (2008) Membrane lipids: where they are and how they behave. Nat Rev Mol Cell Bio 9: 112-124.
2. Schinkel AH, Jonker JW, (2003) Mammalian drug efflux transporters of the ATP binding cassette (ABC) family: an overview. Adv Drug Deliv Rev 55: 3-29.
3. L LU, Olesen H, L, Nyvold GC, Eriksen J, Jakobsen P, et al. (2007) Human intestinal P-glycoprotein activity estimated by the model substrate digoxin. Scand J Clin Lab Invest 67: 123-134.
4. Chen KG, Sikic BI, (2012) Molecular pathways: regulation and therapeutic implications of multidrug resistance. Clin Cancer Res 18: 1863-1869.
5. Lee CA, Cook JA, Reyner EL, Smith DA, (2010) P-glycoprotein related drug interactions: clinical importance and a consideration of disease states. Expert Opin Drug Metab Toxicol 6: 603-619.
6. Vogelgesang S, Jedlitschky G, Brenn A, Walker LC, (2011) The Role of the ATP-Binding Cassette Transporter P-Glycoprotein in the Transport of β-Amyloid Across the Blood-Brain Barrier. Curr Pharm Des 17: 2778-2786.
7. Zhang D, Fan D, (2010) New insights into the mechanisms of gastric cancer multidrug resistance and future perspectives. Future Oncol 6: 527-537.
8. Yuferov V, Levran O, Proudnikov D, Nielsen DA, (2010) Search for genetic markers and functional variants involved in the development of opiate and cocaine addiction and treatment. Ann NY Acad Sci 1187: 184-207.
9. Palmeira A, Sousa E, Vasconcelos MH, Pinto MM, (2012) Three decades of P-gp inhibitors: skimming through several generations and scaffolds. Curr Med Chem 19: 1946-2025.
10. Amiri-Kordestani L, Basseville A, Kurdziel K, Fojo AT, Bates SE, (2012) Targeting MDR in breast and lung cancer: Discriminating its potential importance from the failure of drug resistance reversal studies. Drug Resist Updat 15: 50-61.
11. Chiu YY, Higaki K, Neudeck BL, Barnett JL, Welage LS, et al. (2003) Human jejunal permeability of cyclosporin A: influence of surfactants on P-glycoprotein efflux in Caco-2 cells. Pharm Res 20: 749-756.
12. Regea BD, Kao JPY, Polli JE, (2002) Effects of nonionic surfactants on membrane transporters in Caco-2 cell monolayers. Eur J Pharm Sci 16: 237-246.
13. Batrakova EV, Li S, Li Y, Alakhov VY, Kabanov AV, (2004) Effect of Pluronic P85 on ATPase Activity of Drug Efflux Transporters. Pharm Res 21: 2226-2233.
14. Li-Blatter X, Beck A, Seelig A, (2012) P-Glycoprotein-ATPase Modulation: The Molecular Mechanisms. Biophys J 102: 1383-1393.
15. Maki N, Moitra K, Ghosh P, Dey S, (2006) Allosteric modulation bypasses the requirement for ATP hydrolysis in regenerating low affinity transition state conformation of human P-glycoprotein. J Biol Chem 281: 10769-10777.
16. Sharom FJ, (2006) Shedding light on drug transport: structure and function of the P-glycoprotein multidrug transporter (ABCB1). Biochem Cell Biol 84: 979-992.
17. Romsicki Y, Sharom FJ, (1999) The membrane lipid environment modulates drug interactions with the P-glycoprotein multidrug transporter. Biochemistry 38: 6887-6896.
18. Simon S, Schubert R, (2012) Inhibitory effect of phospholipids on P-glycoprotein: Cellular studies in Caco-2, MDCKII mdr1 and MDCKII wildtype cells and P-gp ATPase activity measurements. Biochim Biophys Acta 1821: 1211-1223.
19. Lee JY, Kim YR, Park J, Kim S, (2012) Inositol polyphosphate multikinase signaling in the regulation of metabolism. Ann N Y Acad Sci 1271: 68-74.
20. McLaughlin S, Murray D, (2005) Plasma membrane phosphoinositide organization by protein electrostatics. Nature 438: 605-611.
21. Moss SM, (2012) How Actin Gets the PIP. Sci Signal 5: pe7.
22. Brill JA, Wong R, Wilde A, (2011) Phosphoinositide function in cytokinesis. Curr Biol 21: R930-934.
23. Ernst R, Kueppers P, Stindt J, Kuchler K, Schmitt L, (2010) Multidrug efflux pumps: substrate selection in ATP-binding cassette multidrug efflux pumps-first come, first served? FEBS J 277: 540-549.
24. Lugo MR, Sharom FJ, (2005) Interaction of LDS-751 and rhodamine 123 with P-glycoprotein: evidence for simultaneous binding of both drugs. Biochemistry 44: 14020-14029.
25. Orlowski S, Mir LM, Belehradek J Jr, Garrigos M, (1996) Effects of steroids and verapamil on P-glycoprotein ATPase activity: progesterone, desoxycorticosterone, corticosterone and verapamil are mutually non-exclusive modulators. Biochem J 317 (Pt 2): 515-522.
26. Higgins CF, (2007) Multiple molecular mechanisms for multidrug resistance transporters. Nature 446: 749-757.
27. Aller SG, Yu J, Ward A, Weng Y, Chittaboina S, et al. (2009) Structure of P-glycoprotein reveals a molecular basis for poly-specific drug binding. Science 323: 1718-1722.
28. Klepsch F, Chiba P, Ecker GF, (2011) Exhaustive sampling of docking poses reveals binding hypotheses for propafenone type inhibitors of P-glycoprotein. PLoS Comput Biol 7: e1002036.
29. Arnold K, Bordoli L, Kopp J, Schwede T, (2006) The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling. Bioinformatics 22: 195-201.
30. Giardine B, Riemer C, Hardison RC, Burhans R, Elnitski L, et al. (2005) Galaxy: a platform for interactive large-scale genome analysis. Genome Res 15: 1451-1455.
31. The Dictionary of Natural Products.
32. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, et al. (2012) ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res 40: D1100-1107.
33. Irwin JJ, Shoichet BK, (2005) ZINC-a free database of commercially available compounds for virtual screening. J Chem Inf Model 45: 177-182.
34. Collnot EM, Baldes C, Schaefer UF, Edgar KJ, Wempe MF, et al. (2010) Vitamin E TPGS P-glycoprotein inhibition mechanism: influence on conformational flexibility, intracellular ATP levels, and role of time and site of access. Mol Pharm 7: 642-651.
35. Hidalgo IJ, Raub TJ, Borchardt RT, (1989) Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability. Gastroenterology 96: 736-749.
36. Meunier V, Bourrie M, Berger Y, Fabre G, (1995) The human intestinal epithelial cell line Caco-2; pharmacological and pharmacokinetic applications. Cell Biol Toxicol 11: 187-194.
37. Cevc G (1993) Phospholipid Handbook. New York.
38. Feng B, Mills JB, Davidson RE, Mireles RJ, Janiszewski JS, et al. (2008) In vitro P-glycoprotein assays to predict the in vivo interactions of P-glycoprotein with drugs in the central nervous system. Drug Metab Dispos 36: 268-275.
39. Matsunaga N, Shimazawa M, Otsubo K, Hara H, (2008) Phosphatidylinositol inhibits vascular endothelial growth factor-A-induced migration of human umbilical vein endothelial cells. J Pharmacol Sci 106: 128-135.
40. Wallace MA, (1994) Effects of Alzheimer's disease-related beta amyloid protein fragments on enzymes metabolizing phosphoinositides in brain. Biochim Biophys Acta 1227: 183-187.
41. Zhang NY, Kitagawa K, Hattori N, Nakayama Y, Xiong ZM, et al. (2007) Soybean-derived phosphatidylinositol inhibits in vivo low concentrations of amyloid beta protein-induced degeneration of hippocampal neurons in V337M human tau-expressing mice. Life Sci 80: 1971-1976.
42. Burgess JW, Neville TA, Rouillard P, Harder Z, Beanlands DS, et al. (2005) Phosphatidylinositol increases HDL-C levels in humans. J Lipid Res 46: 350-355.
43. Shimizu K, Ida T, Tsutsui H, Asai T, Otsubo K, et al. (2010) Anti-obesity Effect of Phosphatidylinositol on Diet-Induced Obesity in Mice. J Agric Food Chem.