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Research Article

Neither lipophilicity nor membrane-perturbing potency of phenothiazine maleates correlate with the ability to inhibit P-glycoprotein transport activity

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Pages 53-60 | Published online: 09 Jul 2009

References

  • Bosch, I. and Croop, J., 1996, P-glycoprotein multidrug resis- tance and cancer. Biochimica et Biophysica Acta, 1288, F37 - F54.
  • Van Kalken, C. K., Pinedo, H. M. and Giaccone, G., 1991, Multidrug resistance from the clinical point of view. European Journal of Cancer, 27, 1481 -1486.
  • Chauncey, T. R., 2001, Multidrug resistance mechanisms in acute leukemia. Current Opinion in Oncology, 13, 21 -26.
  • Legrand, O., Simonin, G., Beauchamp-Nicoud, A., Zittoun, R. and Marie, J. P., 1999, Simultaneous activity of MRP1 and Pdp is correlated with in vitro resistance to daunorubicin and with in vivo resistance in adult acute myeloid leukemia. Blood, 94, 1046 -1056.
  • Raderer, M. and Scheithauer, W., 1993, Clinical trials of agents that reverse multidrug resistance. A literature review. Cancer, 72, 3553 -3563.
  • Akiyama, S., Cornwell, W. M., Kuwano, M., Pastan, I. and Gottesman, M. M., 1988, Most drugs that reverse multidrug resistance also inhibit photoaffinity labeling of P-glycoprotein by a vinblastine analog. Molecular Pharmacology, 33, 144 -147.
  • Foxwell, B. M. J., Mackie, A., Ling, V. and Ryffel, B., 1989, Identification of the multidrug resistance-related P-glycoprotein as a cyclosporin binding protein. Molecular Pharmacology, 36, 543 -546.
  • Callaghan, R. and Higgins, C. F., 1995, Interaction of tamoxifen with the multidrug resistance P-glycoprotein. British Journal of Cancer, 71, 294 -299.
  • Pearce, H. L., Gottesman, M. M., Ueda, K., Lovelace, E., Rutheford, A. V. and Willingham, M. C., 1989, Essential features of the P-glycoprotein pharmacophore as defined by a series of reserpine analogs that modulate multidrug resistance. Proceedings of the National Academy of Sciences, USA, 86, 5128 -5132.
  • Ford, J. M., Bruggemann, E. P., Pastan, I., Gottesman, M. M. and Hait, W. N., 1990, Cellular and biochemical characterization of thioxanthenes for reversal of multidrug resistance in human and murine cell lines. Cancer Research, 50, 1748 -1756.
  • Liu, R. and Sharom, F. J., 1996, Site-directed fluorescence labeling of P-glycoprotein on cysteine residues in the nucleotide binding domains. Biochemistry, 35, 11865–11873.
  • Liu, R., Siemiarczuk, A. and Sharom, F. J., 2000, Intrinsic fluorescence of the P-glycoprotein multidrug transporter: sensi- tivity of tryptophan residues to binding of drugs and nucleotides. Biochemistry, 39, 14927–14938.
  • Romsicki, Y. and Sharom, F. J., 1999, The membrane lipid environment modulates drug interactions with the P-glycopro- tein multidrug transporter. Biochemistry, 38, 6887 -6896.
  • Shapiro, A. B. and Ling, V., 1997, Extraction of Hoechst 33342 from the cytoplasmic leaflet of the plasma membrane by P- glycoprotein. European Journal of Biochemistry, 250, 122 -129.
  • Ferte, J., 2000, Analysis of the tangled relationships between P- glycoprotein-mediated multidrug resistance and the lipid phase of the cell membrane. European Journal of Biochemistry, 267, 277 -294.
  • Wadkins, R. M. and Houghton, P. J., 1993, The role of drug -lipid interactions in the biological activity of modulators of multi- drug resistance. Biochimica et Biophysica Acta, 1153, 225 - 236.
  • Castaing, M., Brouant, P., Loiseau, A., Santelli-Rouvier, C., Santelli, M., Alibert-Franco, S., Mahamoud, A. and Barbe, J., 2000, Membrane permeation by multidrug-resistance-modulators and non-modulators: effects of hydrophobicity and electric charge. Journal of Pharmacy and Pharmacology, 52, 289 -296. [18] Eytan, G. D., Regev, R., Oren, G. and Assaraf, Y. G., 1996, The role of passive transbilayer drug movement in multidrug resistance and its modulation. Journal of Biological Chemistry, 271, 12897–12902.
  • Tsuruo, T., Iida, H., Tsukagoshi, S. and Sakurai, Y., 1982, Increased accumulation of vincristine and adriamycin in drug- resistant P388 tumor cells following incubation with calcium antagonists and calmodulin inhibitors. Cancer Research, 42, 4730 -4733.
  • Molna´r, J., Hever, A., Fakla, I., Ocsovski, I. and Aszalos, A., 1997, Inhibition of the transport function of membrane proteins by some substituted phenothiazines in E. coli and multidrug resistant tumor cells. Anticancer Research, 17, 481 -486.
  • Molna´r, J., Szabo, D., Ma´ ndi, Y., Mucsi, I., Fischer, J., Varga, A., Ko¨ nig, S. and Motohashi, N., 1998, Multidrug resistance reversal in mouse lymphoma cells by heterocyclic compounds. Anticancer Research, 18, 3033 -3038.
  • Motohashi, N., Kurihara, T., Kawase, M., Hever, A., Tanaka., M., Szabo, D., Nacsa, J., Yamanaka, W., Kerim, A. and Molna´ r, J., 1997, Drug resistance reversal, anti-mutagenicity and antiretroviral effect of phtalimido- and chloroethyl-phenothia- zines. Anticancer Research, 17, 3537 -3544.
  • Zamora, J. M., Pearce, H. L. and Beck, W. T., 1988, Physical -chemical properties shared by compounds that modulate multi- drug resistance in human leukemic cells. Molecular Pharmacol- ogy, 33, 454 -462.
  • Frenzel, J., Arnold, K. and Nuhn, P., 1978, Calorimetric, 13C NMR, and 31P NMR studies on the interaction of some phenothiazine derivatives with dipalmitoyl phosphatidylcholine model membranes. Biochimica et Biophysica Acta, 507, 185 -197.
  • Hanpft, R. and Mohr, K., 1985, Influence of cationic amphiphilic drugs on the phase-transition temperature of phospholipids with different polar headgroups. Biochimica et Biophysica Acta, 814, 156 -162.
  • Nerdal, W., Gundersen, S. A., Thorsen, V., Hoiland, H. and Holmsen, H., 2000, Chlorpromazine interaction with glycero- phospholipid liposomes studied by magic angle spinning solid state 13C-NMR and differential scanning calorimetry. Biochi-mica et Biophysica Acta, 1464, 165 -175.
  • Hendrich, A. B., Wesolowska, O. and Michalak, K., 2001a, Trifluoperazine induces domain formation in zwitterionic phos- phatidylcholine but not in charged phosphatidylglycerol bilayers. Biochimica et Biophysica Acta, 1510, 414 -425.
  • Hendrich, A. B., Wesolowska, O. and Michalak, K., 2001b, Differences and similarities in the influence of trifluoperazine on the phase transitions of phosphatidylcholine and phosphatidy- lethanolamine. Current Topics in Biophysics, 25, 67 -69.
  • Wesolowska, O., Hendrich, A. B., Motohashi, N. and Michalak, K., 2001, Phenothiazine derivative causes phase separation in phosphatidylethanolamine model membranes. Current Topics in Biophysics, 25, 71 -73.
  • Varnier-Agasoester, A., Tungodden, L. M., Cejka, D., Bakstad, E., Sydnes, L. K. and Holmsen, H., 2001, Chorpromazine- induced increase in dipalmitoylphosphatidylserine surface area in monolayers at room temperature. Biochemical Pharmacol- ogy, 61, 817 -825.
  • Isomaa, B., Ha¨ gerstrand, H. and Paatero, G., 1987, Shape transformations induced by amphiphiles in erythrocytes. Biochi- mica et Biophysica Acta, 899, 93 -103.
  • Rosso, J., Zachowski, A. and Devaux, P. F., 1988, Influence of chorpromazine on the transverse mobility of phospholipids in human erythrocyte membrane: relation to shape changes. Biochimica et Biophysica Acta, 942, 271 -279.
  • Malheiros, S. V., de Paula, E. and Meirelles, N. C., 1998, Contribution of trifluoperazine/lipid ratio and drug ionization to hemolysis. Biochimica et Biophysica Acta, 1373, 332 -340.
  • Ford, J. M., Prozialeck, W. C. and Hait, W. N., 1989, Structural features determining activity of phenothiazines and related drugs for inhibition of cell growth and reversal of multidrug resistance. Molecular Pharmacology, 35, 105 -115.
  • Takegami, S., Kitamura, K., Kitade, T., Hasegawa, K. and Nishihira, A., 1999, Effects of particle size and cholesterol content on the partition coefficients of chlorpromazine and triflupromazine between phosphatidylcholine -cholesterol bi- layers of unilamellar vesicles and water studied by second- derivative spectrophotometry. Journal of Colloid and Interface Science, 220, 81 -87.
  • Kitamura, K., Imayoshi, N., Goto, T., Shiro, H., Mano, T. and Nakai, Y., 1995, Second derivative spectrophotometric deter- mination of partition coefficients of chlorpromazine and proma- zine between lecithin bilayer vesicles and water. Analytica Chimica Acta, 304, 101 -106.
  • Matayoshi, E. D. and Kleinfeld, A. M., 1981, Emission-wave- length-dependent decay of the fluorescent probe N-phenyl-1- naphthylamine. Biochimica et Biophysica Acta, 644, 233 -243. [38] Kaiser, R. D. and London, E., 1998, Location of diphenylhex-atriene (DPH) and its derivatives within membranes: compar- ison of different fluorescence quenching analyses of membrane depth. Biochemistry, 37, 8180–8190.
  • Hendrich, A. B., Wesolowska, O., Komorowska, M., Motohashi, N. and Michalak, K., 2002, The alterations of lipid bilayer fluidity induced by newly synthesized phenothiazine derivative. Bio- physical Chemistry, 98, 275 -285.
  • Radda, G. K., 1975, Fluorescent probes in membrane studies. In E. D. Korn, ed. Methods in Membrane Biology (Plenum, New York), pp. 97 -188.
  • Pajeva, I. K., Wiese, M., Cordes, H. P. and Seydel, J. K., 1996, Membrane interactions of some catamphilic drugs and relation to their multidug-resistance-reversing ability. Journal of Cancer Research and Clinical Oncology, 122, 27 -40.
  • Ramu, A. and Ramu, N., 1992, Reversal of multidrug resistance by phenothiazines and structurally related compounds. Cancer Chemotherapy and Pharmacology, 30, 165 -173.
  • Motohashi, N., Kawase, M., Saito, S., Kurihara, T., Satoh, K., Nakashima, H., Premanathan, M., Arakaki, R., Sakagami, H. and Molnar, J., 2000, Synthesis and biological activity of N- acylphenothiazines. International Journal of Antimicrobial Agents, 14, 203 -207.
  • Rodrigues, C., Gameiro, P., Reis, S., Lima, J. L. F. C. and de Castro, B., 2001, Derivative spectrophotometry as a tool for the determination of drug partition coefficients in water/dimyristoyl- L-(-phosphatidylglycerol (DMPG) liposomes. Biophysical Chemistry, 94, 97 -106.
  • Minderman, H., Vanhoefer, U., Toth, K., Yin, M. B., Minderman,M. D., Wrzosek, C., Slovak, M. L. and Rustum, Y. M., 1996, DiOC2(3) is not a substrate for multidrug resistance protein (MRP)-mediated drug efflux. Cytometry, 25, 14 -20.
  • Bosch, I., Crankshaw, C. L., Piwnica-Worms, D. and Croop, J. M., 1997, Characterization of functional assays of multidrug resistance P-glycoprotein transport activity. Leukemia, 11, 1131 -1137.
  • Pastan, I., Gottesman, M. M., Ueda, K., Lovelace, E., Ruthe- ford, A. V. and Willingham, M. C., 1988, A retrovirus carrying an MDR-1 cDNA confers multidrug resistance and polarized expression of P-glycoprotein in MDCK cells. Proceedings of the National Academy of Sciences, USA, 85, 4486 -4490.
  • Weaver, J. L., Szabo, G., Pine, P. S., Gottesman, M. M., Goldenberg, S. and Aszalos, A., 1993, The effect of ion channel blockers, immunosupressive agents, and other drugs on the activity of the multi-drug transporter. International Journal of Cancer, 54, 456 -461.

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