Arylmethyloxyphenyl derivatives: Small molecules displaying P-glycoprotein inhibition

Journal of Medicinal Chemistry

Volumn 49, Issue 22, 2006, Pages 6607-6613

  Colabufo, Nicola Antonio ^a   Berardi, Francesco ^a   Perrone, Roberto ^a   Rapposelli, Simona ^b   Digiacomo, Maria ^b   Balsamo, Aldo ^b  

^a UNIVERSITY OF BARI   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 [(3 METHOXYBENZYL)OXY] 2 [2 (3 METHOXYPHENYL)ETHYL]BENZENE; 2 [[2 [2 (3 METHOXYPHENYL)ETHYL]PHENOXY]METHYL]PYRIDINE; BENZENE DERIVATIVE; DOXORUBICIN; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; METHYLOXYPHENYL DERIVATIVE; UNCLASSIFIED DRUG; VERAPAMIL; VINBLASTINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACCUMULATION; DRUG PROTEIN BINDING; DRUG RECEPTOR BINDING; ENZYME ACTIVATION; ENZYME SUBSTRATE; FLOW CYTOMETRY; HUMAN; HUMAN CELL; INHIBITION KINETICS; MULTIDRUG RESISTANCE; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ADENOSINE TRIPHOSPHATASES; ADENOSINE TRIPHOSPHATE; ANTIBIOTICS, ANTINEOPLASTIC; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BIOLOGICAL TRANSPORT, ACTIVE; CACO-2 CELLS; CELL LINE; DOSE-RESPONSE RELATIONSHIP, DRUG; DOXORUBICIN; FLOW CYTOMETRY; HUMANS; P-GLYCOPROTEIN; PIPERAZINES; RECEPTOR, SEROTONIN, 5-HT1A; RECEPTORS, DOPAMINE D2; VINBLASTINE;

EID: 33750449337     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060639z     Document Type: Article

References (34)

1. Bates, E. S.; Robey, R.; Knutsen, T.; Honjo, Y.; Litman, T.; Dean, M. New ABC transporters in multi-drug resistance. Emerging Ther. Targets 2000, 4, 561-580.
2. Gottesman, M. M.; Fojo, T.; Bates, S. E. Multidrug resistance in cancer: role of ATP-dependent transporters. Nat. Rev. Cancer 2002, 2, 48-58.
3. Ambudkar, S. V.; Dey, S.; Hrycyna, C. A.; Ramachandra, M.; Pastan, I.; Gottesman, M. M. Biochemical, cellular, and pharmacological aspects of the multidrug transporter. Annu. Rev. Pharmacol. Toxicol. 1999, 39, 361-398.
4. Thomas, H.; Coley, H. M. Overcoming multidrug resistance in cancer: an update on the clinical strategy of inhibiting P-glycoprotein. Cancer Control 2003, 10, 159-164.
5. Leslie, E. M.; Deeley, R. G.; Cole, S. P. C. Multidrug resistance proteins: role of P-glycoprotein MRP1, MRP2, and BCRP (ABCG2) in tissue defense. Toxicol. Appl. Pharmacol. 2005, 204, 216-237.
6. Schneider, E.; Paul, D.; Ivy, P.; Cowan, K. H. Multidrug resistance. Cancer Chemother. Biol. Response Modif. 1999, 18, 152-177.
7. Fardel, O.; Lecureur, V.; Guillouzo, A. The P-glycoprotein multidrug transporter. Gen. Pharmacol. 1996, 39, 361-398.
8. Ferry, D. R.; Traunecker, H.; Kerry, D. J. Clinical trials of P-glycoprotein reversal in solid tumours. Eur. J. Cancer. 1996, 32A, 1070-1081.
9. Krishna, R.; Mayer, L. D. Multidrug resistance (MDR) in cancer. Mechanisms, reversal using modulators of MDR and the role of MDR modulators in influencing the pharmacokinetics of anticancer drugs. Eur. J. Pharmacol. Sci. 2000, 11, 265-283.
10. te Boekhorst, P. A.; van Kapel, J.; Schoester, M.; Sonneveld, P. Reversal of typical multidrug resistance by cyclosporin and its non-immunosuppressive analogue SDZ PSC 833 in Chinese hamster ovary cells expressing the mdr1 phenotype. Cancer Chemother. Pharmacol. 1992, 30, 238-242.
11. Twentyman, P. R.; Bleehen, N. M. Resistance modifaction by PSC-833, a novel non-immunosuppressive cyclosporin. Eur. J. Cancer. 1991, 27, 1639-1642.
12. Advani, R.; Saba, H. I.; Tallman, M. S.; Rowe, J. M.; Wiernik, P. H.; Ramek, J.; Dugan, K.; Lum, B.; Villena, J.; Davis, E.; Paietta, E.; Litchman, M.; Sikic, B. I.; Greenberg, P. L. Treatment of refractory and relapsed acute myelogenous leukaemia with combination chemotherapy plus the multidrug resistance modulator PSC 833 (Valspodar). Blood 1999, 93, 787-795.
13. Chico, I, Kang, M. H.; Bergan, R.; Abraham, J.; Bakke, S.; Meadows, B.; Rutt, A.; Robey, R.; Choyke, P.; Merino, M.; Goldspiel, B.; Smith, T.; Steinberg, S.; Figg, W. D.; Fpjo, T.; Bates, S. Phase I study of infusional paclitaxel in combination with the P-glycoprotein antagonist PSC 833. J. Clin. Oncol. 2001, 19, 832-842.
14. Yanagisawa, T.; Newman, A.; Coley, H.; Renshaw, J.; Pinkerton, C. R.; Pritchard-Jones. K. BIRICODAR (VX-710; Incel): an effective chemosensitizer in neuroblastoma. Br. J. Cancer 1999, 80, 1190-1196.
15. Rowinsky, E. K.; Smith, L.; Wang, Y. M.; Chatuverdi, P.; Villalona, M.; Campbell, E.; Aylesworth, C.; Eckhardt, S. G.; Hammond, L.; Kraynak, M.; Drengler, R.; Stephenson, J., Jr.; Harding, M. W.; Von Hoff, D. D. Phase I and pharmacokinetic study of paclitaxel in combination with biricodar, a novel agent that reverse multidrug resistance conferred by overexpression of both MDR1 and MRP. J. Clin. Oncol. 1998, 16, 2964-2976.
16. Wandel, C.; Kim, R. B.; Kajiji, S.; Guengerich, P.; Wilkinson, G. R.; Wood, A. J. P-glycoprotein and cytochrome P-450 3A inhibition: dissociation of inhibitory potencies. Cancer Res. 1999, 59, 3944-3948.
17. Dantzig, A. H.; Shepard, R. L.; Law, K. L.; Tabas, L.; Pratt, S.; Gillespie, J. S.; Binkley, S. N.; Kuhfeld, M. T.; Starling, J. J.; Wrighton, S. A. Selectivity of the multidrug resistance modulator, LY335979, for P-glycoprotein and effect on cytochrome P-450 activities. J. Pharmacol. Exp. Ther. 1999, 290, 854-862.
18. Mistry, P.; Stewart, A. J.; Dangerfield, W.; Okiji, S.; Liddle, C.; Bootle, D.; Plumb, J. A.; Templeton, D.; Charlton, P. In vitro and in vivo reversal of P-glycoprotein-mediated multidrug resistance by a novel potent modulator, XR9576. Cancer Res. 2001, 61, 749-758.
19. Kruijtzer, C. M. F.; Beijnen, J. H.; Rosing, H.; ten Bokkel Huinink, W. W.; Schot, M.; Jewell, R. C.; Paul, E. M.; Schellens, J. H. M. Increased oral bioavailability of topotecan in combination with the breast cancer resistance protein and P-glycoprotein inhibitor GF120918. J. Clin. Oncol. 2002, 20, 2943-2950.
20. Breedveld, P.; Beijnen, J. H.; Shellens, J. H. M. Use of P-glycoprotein and BCRP inhibitors to improve oral bioavailability and CNS penetration of anticancer drugs. Trends Pharmacol. Sci. 2006, 27, 17-24.
21. Fromm, M. F. P-glycoprotein: a defense mechanism limiting oral bioavailability and CNS accumulation of drugs. Int. J. Clin. Pharmacol. Ther. 2000, 38, 69-74.
22. Loscher, W.; Potschka, H. Role of drug efflux transporters in the brain for drug disposition and treatment of brain diseases. Prog. Neurobiol. 2005, 76, 22-76.
23. 1A/D-2 activity of a new model of arylpiperazines: 1-aryl-4-[3-(1,2-dihydronaphthalen-4-yl)-n- propyl]piperazines. 1. Synthesis and structure-activity relationships. J. Med. Chem. 1994, 37, 99-104.
24. 1A receptor of 1-aryl-4-[(1-tetralin)alkyl]- piperazines. 2. J. Med. Chem. 1995, 38, 942-949.
25. 1A receptor affinity of 1-phenyl-4-[ω- (α-or β-tetralinyl)alkyl]piperazines. 4. J. Med. Chem. 1996, 38, 4928-4934.
26. Unpublished results.
27. Artursson, P.; Karlsson, J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem. Biophys. Res. Commun. 1991, 175, 880-885.
28. Taub, M. E.; Podila, L.; Almeida, I. Functional assessment of multiple P-glycoprotein (P-gp) probe substrate: influence of cell line and modulator concentration on P-gp activity. Drug Metab. Dispos. 2005, 33, 1679-1687.
29. Azzariti, A.; Colabufo, N. A.; Berardi, F.; Porcelli, L.; Niso, M.; Simone, M. G.; Perrone, R.; Paradiso, A. Cyclohexylpiperazine derivative PB28, a sigma-2 agonist and sigma-1 antagonist receptor activity, inhibits cell growth, modulates P-glycoprotein and synergizes with anthracyclines in brest cancer. Mol. Cancer Ther. 2006, 5, 1807-1816.
30. Kikumoto, R.; Hara, H.; Ninomiya, K.; Osakabe, M.; Sugano M.; Fukami, H.; Tamao, Y. Syntheses and platelet aggregation inhibitory and antithrombotic properties of [2-[(ω-aminoalkoxy)phenyl] ethyl]-benzenes. J. Med. Chem. 1990, 33, 1818-1823.
31. Kikumoto, R.; Tobe, A.; Fukami, H.; Egawa, M. Substituted (ω-aminoalkoxy)stilbene derivatives as a new class of anticonvulsants. J. Med. Chem. 1984, 27, 645-649.
32. Kangas, L.; Grönroos, M.; Nieminem, A. L. Bioluminescence of cellular ATP: a new method for evaluating agents in vitro. Med. Biol. 1984, 62, 338-343.
33. Polli, J. W.; Wring, S. A.; Humphreys, J. E.; Huang, L.; Morgan, J. B.; Webster, L. O.; Serabjit-Singh, C. S. Rational use of in vitro P-glycoprotein assays in drug discovery. J. Pharmacol. Exp. Ther. 2001, 299, 620-628.
34. Colabufo, N. A.; Berardi, F.; Contino, M.; Fazio, F.; Matarrese, M.; Moresco, R. M.; Niso, M.; Perrone, R.; Tortorella, V. Distribution of sigma receptor in EMT-6 cells: preliminary biological evaluation of PB167 and potential for in-vivo PET. J. Pharm. Pharmacol. 2005, 57, 1453-1459.