The ability of molecular docking to unravel the controversy and challenges related to P-glycoprotein - A well-known, yet poorly understood drug transporter

Investigational New Drugs

Volumn 32, Issue 4, 2014, Pages 618-625

  Zeino, Maen ^a   Saeed, Mohamed E M ^a   Kadioglu, Onat ^a   Efferth, Thomas ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

ABC transporter; Cancer; Chemotherapy; Multidrug resistance

Indexed keywords

APIGENIN; HOE 33342; MULTIDRUG RESISTANCE PROTEIN; VERAPAMIL; CARRIER PROTEIN; DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; CRYSTAL STRUCTURE; DRUG PROTEIN BINDING; HUMAN; LIGAND BINDING; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN DOMAIN; STATISTICAL ANALYSIS; X RAY CRYSTALLOGRAPHY; METABOLISM; PHYSIOLOGY; PROCEDURES; TRANSPORT AT THE CELLULAR LEVEL;

BINDING SITES; BIOLOGICAL TRANSPORT; HUMANS; MEMBRANE TRANSPORT PROTEINS; MOLECULAR DOCKING SIMULATION; P-GLYCOPROTEIN; PHARMACEUTICAL PREPARATIONS;

EID: 84904564955     PISSN: 01676997     EISSN: 15730646     Source Type: Journal    
DOI: 10.1007/s10637-014-0098-1     Document Type: Article

References (40)

1. Ferlay J, Shin HR, Bray F, Forman D, Mathers C, Parkin DM (2010) Estimates of worldwide burden of cancer in 2008: GLOBOCAN 2008. Int J Cancer 127:2893-917
2. Katzung BG (2007) Basic and Clinical Pharmacology. 10th edition, p 879.
3. Andreoli TE, Bennet JC, Carpenter CCJ, Plum F (1997) Cecil Essentials of Medicine. 4th edition, p 425.
4. Tsuruo T, Iida H, Tsukagoshi S, Sakurai Y (1981) Overcoming of vincristine resistance in P388 leukemia in vivo and in vitro through enhanced cytotoxicity of vincristine and vinblastine by verapamil. Cancer Res 41:1967-72 (Pubitemid 11114605)
5. 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
6. Fudin J, Fontenelle DV, Fudin HR, Carlyn C, Hinden DA, Ashley CC (2013) Potential P-glycoprotein pharmacokinetic interaction of telaprevir with morphine or methadone. J Pain Palliat Care Pharmacother 27:261-7
7. Robey RW, Shukla S, Finley EM, Oldham RK, Barnett D, Ambudkar SV, Fojo T, Bates SE (2008) Inhibition of P-glycoprotein (ABCB1)-and multidrug resistance-associated protein 1 (ABCC1)- mediated transport by the orally administered inhibitor, CBT-1((R)). Biochem Pharmacol 75:1302-12
8. Leitner I, Nemeth J, Feurstein T, Abrahim A, Matzneller P, Lagler H, Erker T, Langer O, Zeitlinger M (2011) The third-generation P-glycoprotein inhibitor tariquidar may overcome bacterial multidrug resistance by increasing intracellular drug concentration. J Antimicrob Chemother 66:834-9
9. Coley HM (2010) Overcoming multidrug resistance in cancer: clinical studies of p-glycoprotein inhibitors. In Multi-Drug Resistance in Cancer, Humana Press, pp. 341-358.
10. Holland IB, Cole SPC, Kuchler K, Higgens CF (2003) ABC proteins: from bacteria to man. Elsevier Science, London, 251
11. Brüggemann EP, Germann UA, Gottesman MM, Pastan I (1989) Two different regions of P-glycoprotein [corrected] are photoaffinity-labeled by azidopine. J Biol Chem 264:15483-8 (Pubitemid 19242924)
12. Safa AR (2004) Identification and characterization of the binding sites of P-glycoprotein for multidrug resistance-related drugs and modulators. Curr Med Chem Anticancer Agents 4:1-17
13. Loo TW, Bartlett MC, Clarke DM (2003) Substrate-induced conformational changes in the transmembrane segments of human Pglycoprotein. Direct evidence for the substrate induced fit mechanism for drug binding. J Biol Chem 278:13603-6 (Pubitemid 36799891)
14. Globisch C, Pajeva IK, Wiese M (2008) Identification of putative binding sites of P-glycoprotein based on its homology model. ChemMedChem 3:280-95
15. Maki N, Hafkemeyer P, Dey S (2003) Allosteric modulation of human P-glycoprotein. Inhibition of transport by preventing substrate translocation and dissociation. J Biol Chem 278:18132-9 (Pubitemid 36799427)
16. Badhan R, Penny J (2006) In silico modelling of the interaction of flavonoids with human P-glycoprotein nucleotide-binding domain. Eur J Med Chem 41:285-95
17. Ambudkar SV, Kim IW, Xia D, Sauna ZE (2006) The A-loop, a novel conserved aromatic acid subdomain upstream of the Walker A motif in ABC transporters, is critical for ATP binding. FEBS Lett 580:1049-55 (Pubitemid 43185285)
18. Mechetner EB, Roninson IB (1992) Efficient inhibition of P-glycoprotein-mediated multidrug resistance with a monoclonal antibody. Proc Natl Acad Sci U S A 89:5824-8
19. Georges E, Tsuruo T, Ling V (1993) Topology of P-glycoprotein as determined by epitope mapping of MRK-16 monoclonal antibody. J Biol Chem 268:1792-8 (Pubitemid 23033575)
20. Nagy H, Goda K, Arceci R, Cianfriglia M, Mechetner E, Szabó G Jr (2001) P-Glycoprotein conformational changes detected by antibody competition. Eur J Biochem 268:2416-20 (Pubitemid 32417771)
21. Regev R, Assaraf YG, Eytan GD (1999) Membrane fluidization by ether, other anesthetics, and certain agents abolishes P-glycoprotein ATPase activity and modulates efflux from multidrug resistant cells. Eur J Biochem 259:18-24 (Pubitemid 29030813)
22. Cai C, Zhu H, Chen J (2004) Overexpression of caveolin-1 increases plasma membrane fluidity and reduces P-glycoprotein function in Hs578T/Dox. Biochem Biophys Res Commun 320:868-74 (Pubitemid 38887223)
23. Wang YH, Li Y, Yang SL, Yang L (2005) Classification of substrates and inhibitors of P-glycoprotein using unsupervised machine learning approach. J Chem Inf Model 45:750-7 (Pubitemid 40795178)
24. Kim RB (2002) Drugs as P-glycoprotein substrates, inhibitors, and inducers. Drug Metab Rev 34:47-54
25. Choi CH (2005) ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal. Cancer Cell Int 5:30
26. Bolton E, Wang Y, Thiessen PA, Bryant SH (2008) PubChem: integrated platform of small molecules and biological activities. Chapter 12 IN annual reports in computational chemistry, volume 4. American Chemical Society, Washington
27. Sadowski J, Gasteiger J, Klebe G (1994) Comparison of automatic three-dimensional model builders using 639 X-Ray structures. J Chem Inf Comput Sci 34:1000-8
28. Tajima Y, Nakagawa H, Tamura A, Kadioglu O, Satake K, Mitani Y, Murase H, Regasini LO, da Silva Bolzani V, Ishikawa T, Fricker G, Efferth T (2013) Nitensidine A, a guanidine alkaloid from Pterogyne nitens, is a novel substrate for human ABC transporter ABCB1. Phytomedicine [Epub ahead of print]
29. Zeino M, Zhao Q, Eichhorn T, Hermann J, Müller R, Efferth T (2013) Molecular docking studies of myxobacterial disorazoles and tubulysins to tubulin. J Biosci Med 3:31-43
30. Hartmann J (2000) Choosing the correct statistical test. University of Alabama, USA, http://bama.ua.edu/~jleeper/627/choosestat.html, last retrieved: 12.12.2013.
31. Wise JG (2012) Catalytic transitions in the human MDR1 P-glycoprotein drug binding sites. Biochemistry 51:5125-41
32. 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
33. Tang F, Ouyang H, Yang JZ, Borchardt RT (2004) Bidirectional transport of rhodamine 123 and Hoechst 33342, fluorescence probes of the binding sites on P-glycoprotein, across MDCKMDR1 cell monolayers. J Pharm Sci 93:1185-94 (Pubitemid 38529692)
34. Loo TW, Clarke DM (2002) Location of the rhodamine-binding site in the human multidrug resistance P-glycoprotein. J Biol Chem 277:44332-8 (Pubitemid 36157868)
35. Ferreira RJ, Ferreira MJ, dos Santos DJ (2013) Molecular docking characterizes substrate binding sites and efflux modulation mechanisms within P-glycoprotein. J Chem Inf Model 53:1747-60
36. Shapiro AB, Ling V (1997) Positively cooperative sites for drug transport by P-glycoprotein with distinct drug specificities. Eur J Biochem 250:130-7 (Pubitemid 27504592)
37. Loo TW, Clarke DM (2001) Defining the drug-binding site in the human multidrug resistance P-glycoprotein using a methanethiosulfonate analog of verapamil, MTS-verapamil. J Biol Chem 276:14972-9
38. Kothandan G, Gadhe CG, Madhavan T, Choi CH, Cho SJ (2011) Docking and 3D-QSAR (quantitative structure activity relationship) studies of flavones, the potent inhibitors of p-glycoprotein targeting the nucleotide binding domain. Eur J Med Chem 46:4078-88
39. Bansal T, Jaggi M, Khar RK, Talegaonkar S (2009) Emerging significance of flavonoids as P-glycoprotein inhibitors in cancer chemotherapy. J Pharm Pharm Sci 12:46-78
40. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ (2009) AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 30:2785-91