Detergents as intrinsic P-glycoprotein substrates and inhibitors

Biochimica et Biophysica Acta - Biomembranes

Volumn 1788, Issue 10, 2009, Pages 2335-2344

  Li Blatter, Xiaochun ^a   Nervi, Pierluigi ^a   Seelig, Anna ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

C12EO8 (C12E8); Competitive inhibition, P glycoprotein binding site; Triton X 100; Tween 80; Un competitive

Indexed keywords

ADENOSINE TRIPHOSPHATASE; DETERGENT; DODECYLOCTAGLYOL; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; MULTIDRUG RESISTANCE PROTEIN 1; POLYSORBATE 80; TRITON X 100; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL BINDING; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; EMBRYO; FIBROBLAST; GENETIC TRANSFECTION; HYDROGEN BOND; LIPID MEMBRANE; MEMBRANE BINDING; MICELLE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING;

ADENOSINE TRIPHOSPHATASES; ANIMALS; BINDING, COMPETITIVE; BIOLOGICAL TRANSPORT; CELL MEMBRANE; CYCLOSPORINE; DETERGENTS; EMBRYO, MAMMALIAN; ENZYME INHIBITORS; FIBROBLASTS; KINETICS; MEMBRANE LIPIDS; MICE; MICELLES; P-GLYCOPROTEIN; VERAPAMIL;

EID: 70349509283     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2009.07.010     Document Type: Article

References (45)

1. Seelig A., and Gerebtzoff G. Enhancement of drug absorption by noncharged detergents through membrane and P-glycoprotein binding. Expert. Opin. Drug Metab. Toxicol. 2 (2006) 733-752
2. Aanismaa P., Gatlik-Landwojtowicz E., and Seelig A. P-glycoprotein senses its substrates and the lateral membrane packing density: consequences for the catalytic cycle. Biochemistry 47 (2008) 10197-10207
3. Zordan-Nudo T., Ling V., Liu Z., and Georges E. Effects of nonionic detergents on P-glycoprotein drug binding and reversal of multidrug resistance. Cancer Res. 53 (1993) 5994-6000
4. Orlowski S., Selosse M.A., Boudon C., Micoud C., Mir L.M., Belehradek Jr. J., and Garrigos M. Effects of detergents on P-glycoprotein atpase activity: differences in perturbations of basal and verapamil-dependent activities. Cancer Biochem. Biophys. 16 (1998) 85-110
5. Rege B.D., Kao J.P., and Polli J.E. Effects of nonionic surfactants on membrane transporters in Caco-2 cell monolayers. Eur. J. Pharm. Sci. 16 (2002) 237-246
6. Raviv Y., Pollard H.B., Bruggemann E.P., Pastan I., and Gottesman M.M. Photosensitized labeling of a functional multidrug transporter in living drug-resistant tumor cells. J. Biol. Chem. 265 (1990) 3975-3980
7. Urbatsch I.L., and Senior A.E. Effects of lipids on ATPase activity of purified Chinese hamster P-glycoprotein. Arch. Biochem. Biophys. 316 (1995) 135-140
8. Shapiro A.B., and Ling V. Extraction of Hoechst 33342 from the cytoplasmic leaflet of the plasma membrane by P-glycoprotein. Eur. J. Biochem. 250 (1997) 122-129
9. Higgins C.F., and Gottesman M.M. Is the multidrug transporter a flippase?. Trends. Biochem. Sci. 17 (1992) 18-21
10. Szakacs G., Paterson J.K., Ludwig J.A., Booth-Genthe C., and Gottesman M.M. Targeting multidrug resistance in cancer. Nature reviews 5 (2006) 219-234
11. Litman T., Zeuthen T., Skovsgaard T., and Stein W.D. Structure-activity relationships of P-glycoprotein interacting drugs: kinetic characterization of their effects on ATPase activity. Biochim. Biophys. Acta 1361 (1997) 159-168
12. Al-Shawi M.K., Polar M.K., Omote H., and Figler R.A. Transition state analysis of the coupling of drug transport to ATP hydrolysis by P-glycoprotein. J. Biol. Chem. 278 (2003) 52629-52640
13. Gatlik-Landwojtowicz E., Aanismaa P., and Seelig A. Quantification and characterization of P-glycoprotein-substrate interactions. Biochemistry 45 (2006) 3020-3032
14. Dey S., Ramachandra M., Pastan I., Gottesman M.M., and Ambudkar S.V. Evidence for two nonidentical drug-interaction sites in the human P-glycoprotein. Proc. Natl. Acad. Sci. U. S. A. 94 (1997) 10594-10599
15. Shapiro A.B., and Ling V. Transport of LDS-751 from the cytoplasmic leaflet of the plasma membrane by the rhodamine-123-selective site of P-glycoprotein. Eur. J. Biochem. 254 (1998) 181-188
16. Lugo M.R., and Sharom F.J. Interaction of LDS-751 with P-glycoprotein and mapping of the location of the R drug binding site. Biochemistry 44 (2005) 643-655
17. Aller S.G., Yu J., Ward A., Weng Y., Chittaboina S., Zhuo R., Harrell P.M., Trinh Y.T., Zhang Q., Urbatsch I.L., and Chang G. Structure of P-glycoprotein reveals a molecular basis for poly-specific drug binding. Science 323 (2009) 1718-1722
18. Scala S., Akhmed N., Rao U.S., Paull K., Lan L.B., Dickstein B., Lee J.S., Elgemeie G.H., Stein W.D., and Bates S.E. P-glycoprotein substrates and antagonists cluster into two distinct groups. Mol. Pharmacol. 51 (1997) 1024-1033
19. Rosenberg M.F., Velarde G., Ford R.C., Martin C., Berridge G., Kerr I.D., Callaghan R., Schmidlin A., Wooding C., Linton K.J., and Higgins C.F. Repacking of the transmembrane domains of P-glycoprotein during the transport ATPase cycle. EMBO J. 20 (2001) 5615-5625
20. Senior A.E., al-Shawi M.K., and Urbatsch I.L. The catalytic cycle of P-glycoprotein. FEBS Lett. 377 (1995) 285-289
21. Chen M., Abele R., and Tampe R. Peptides induce ATP hydrolysis at both subunits of the transporter associated with antigen processing. J. Biol. Chem. 278 (2003) 29686-29692
22. Ambudkar S.V., Cardarelli C.O., Pashinsky I., and Stein W.D. Relation between the turnover number for vinblastine transport and for vinblastine-stimulated ATP hydrolysis by human P-glycoprotein. J. Biol. Chem. 272 (1997) 21160-21166
23. Omote H., and Al-Shawi M.K. A novel electron paramagnetic resonance approach to determine the mechanism of drug transport by P-glycoprotein. J. Biol. Chem. 277 (2002) 45688-45694
24. Seelig A., and Gatlik-Landwojtowicz E. Inhibitors of multidrug efflux transporters: their membrane and protein interactions. Mini. Rev. Med. Chem. 5 (2005) 135-151
25. Seelig A. The role of size and charge for blood-brain barrier permeation of drugs and fatty acids. J. Mol. Neurosci. 33 (2007) 32-41
26. Gerebtzoff G., and Seelig A. In silico prediction of blood-brain barrier permeation using the calculated molecular cross-sectional area as main parameter. J. Chem. Inf. Model 46 (2006) 2638-2650
27. Omote H., and Al-Shawi M.K. Interaction of transported drugs with the lipid bilayer and P-Glycoprotein through a solvation exchange mechanism. Biophys. J. 90 (2006) 4046-4059
28. Martin C., Berridge G., Higgins C.F., Mistry P., Charlton P., and Callaghan R. Communication between multiple drug binding sites on P-glycoprotein. Mol. Pharmacol. 58 (2000) 624-632
29. Romsicki Y., and Sharom F.J. The membrane lipid environment modulates drug interactions with the P-glycoprotein multidrug transporter. Biochemistry 38 (1999) 6887-6896
30. Aanismaa P., and Seelig A. P-Glycoprotein kinetics measured in plasma membrane vesicles and living cells. Biochemistry 46 (2007) 3394-3404
31. Meier M., Blatter X.L., Seelig A., and Seelig J. Interaction of verapamil with lipid membranes and P-glycoprotein: connecting thermodynamics and membrane structure with functional activity. Biophys. J. 91 (2006) 2943-2955
32. Seelig A. A general pattern for substrate recognition by P-glycoprotein. Eur. J. Biochem. 251 (1998) 252-261
33. Seelig A., Blatter X.L., and Wohnsland F. Substrate recognition by P-glycoprotein and the multidrug resistance-associated protein MRP1: a comparison. Int. J. Clin. Pharmacol. Ther. 38 (2000) 111-121
34. Hegner D. Age-dependence of molecular and functional changes in biological membrane properties. Mech. Ageing. Dev. 14 (1980) 101-118
35. Seelig A. Local anesthetics and pressure: a comparison of dibucaine binding to lipid monolayers and bilayers. Biochim. Biophys. Acta 899 (1987) 196-204
36. Heerklotz H., and Seelig J. Correlation of membrane/water partition coefficients of detergents with the critical micelle concentration. Biophys. J. 78 (2000) 2435-2440
37. Litman T., Zeuthen T., Skovsgaard T., and Stein W.D. Competitive, non-competitive and cooperative interactions between substrates of P-glycoprotein as measured by its ATPase activity. Biochim. Biophys. Acta 1361 (1997) 169-176
38. P. Nervi, X. Li-Blatter, P. Äänismaa, A. Seelig, P-Glycoprotein ATPase activity and transport, Biochim. Biophys. Acta (Biomembranes) (submitted).
39. Seelig A., Alt T., Lotz S., and Holzemann G. Binding of substance P agonists to lipid membranes and to the neurokinin-1 receptor. Biochemistry 35 (1996) 4365-4374
40. Arnulphi C., Sot J., Garcia-Pacios M., Arrondo J.L., Alonso A., and Goni F.M. Triton X-100 partitioning into sphingomyelin bilayers at subsolubilizing detergent concentrations: effect of lipid phase and a comparison with dipalmitoylphosphatidylcholine. Biophys. J. 93 (2007) 3504-3514
41. Seelig A., and Landwojtowicz E. Structure-activity relationship of P-glycoprotein substrates and modifiers. Eur. J. Pharm. Sci. 12 (2000) 31-40
42. Sharom F.J., Yu X., and Doige C.A. Functional reconstitution of drug transport and ATPase activity in proteoliposomes containing partially purified P-glycoprotein. J. Biol. Chem. 268 (1993) 24197-24202
43. Sauna Z.E., Andrus M.B., Turner T.M., and Ambudkar S.V. Biochemical basis of polyvalency as a strategy for enhancing the efficacy of P-glycoprotein (ABCB1) modulators: stipiamide homodimers separated with defined-length spacers reverse drug efflux with greater efficacy. Biochemistry 43 (2004) 2262-2271
44. Alqawi O., and Georges E. The multidrug resistance protein ABCC1 drug-binding domains show selective sensitivity to mild detergents. Biochem. Biophys. Res. Commun. 303 (2003) 1135-1141
45. Tanigawara Y. Role of P-glycoprotein in drug disposition. Ther. Drug Monit. 22 (2000) 137-140