Synthesis and Evaluation of Dihydropyrroloquinolines That Selectively Antagonize P-Glycoprotein

Journal of Medicinal Chemistry

Volumn 47, Issue 6, 2004, Pages 1413-1422

  Lee, Brian D ^a   Li, Zhanjiang ^a   French, Kevin J ^a   Zhuang, Yan ^a   Xia, Zuping ^a   Smith, Charles D ^a  

^a PENN STATE COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOSPORIN A; DOXORUBICIN; GLYCOPROTEIN P; MULTIDRUG RESISTANCE PROTEIN 1; PGP 4008; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AREA UNDER THE CURVE; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; CYTOTOXICITY; DRUG ABSORPTION; DRUG ACCUMULATION; DRUG BLOOD LEVEL; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; INHIBITION KINETICS; MELTING POINT; TUMOR MODEL;

ACETANILIDES; ANIMALS; ANTINEOPLASTIC AGENTS; AREA UNDER CURVE; CELL LINE, TUMOR; DRUG RESISTANCE, MULTIPLE; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HALF-LIFE; HUMANS; MICE; MICE, INBRED BALB C; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS; NEOPLASM TRANSPLANTATION; P-GLYCOPROTEIN; PYRROLES; QUINOLINES; TRANSPLANTATION, HETEROLOGOUS;

EID: 1542268189     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0303204     Document Type: Article

References (45)

1. Juliano, R. L.; Ling, V. A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim. Biophys. Acta 1976, 455, 152-162.
2. Sikic, B.; Fisher, G.; Lum, B.; Halsey, J.; Beketic-Oreskovic, L.; et al. Modulation and prevention of multidrug resistance by inhibitors of P-glycoprotein. Cancer Chemother. Pharmacol. 1997, 40, S13-S19.
3. Ling, V. Multidrug resistance: molecular mechanisms and clinical relevance. Cancer Chemother. Pharmacol. 1997, 40, S3-8.
4. Tan, B. Multidrug resistance transporters and modulation. Appl. Biochem. Biotechnol. 2000, 87, 233-245.
5. Grant, C. E.; Valdimarsson, G.; Hipfner, D. R.; Almquist, K. C.; Cole, S. P.; et al. Overexpression of multidrug resistance-associated protein (MRP) increases resistance to natural product drugs. Cancer Res. 1994, 54, 357-361.
6. Kruh, G. D.; Chan, A.; Myers, K.; Gaughan, K.; Miki, T.; et al. Expression complementary DNA library transfer establishes mrp as a multidrug resistance gene. Cancer Res. 1994, 54, 1649-1652.
7. Cole, S. P.; Bhardwaj, G.; Gerlach, J. H.; Mackie, J. E.; Grant, C. E.; et al. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science 1992, 258, 1650-1654.
8. Horio, M.; Gottesman, M.; Pastan, I. ATP-dependent transport of vinblastine in vesicles from human multidrug-resistant cells. Proc. Natl. Acad. Sci. 1988, 85, 3580-3584.
9. Kartner, N.; Riordan, J. R.; Ling, V. Cell surface P-glycoprotein associated with multidrug resistance in mammalian cell lines. Science 1983, 221, 1285-1288.
10. Goldstein, L. J.; Galski, H.; Fojo, A.; Willingham, M.; Lai, S. L.; et al. Expression of a multidrug resistance gene in human cancers. J. Natl. Cancer Inst. 1989, 81, 116-124.
11. Fojo, A. T.; Ueda, K.; Slamon, D. J.; Poplack, D. G.; Gottesman, M. M.; et al. Expression of a multidrug-resistance gene in human tumors and tissues. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 265-269.
12. Bell, D. R.; Gerlach, J. H.; Kartner, N.; Buick, R. N.; Ling, V. Detection of P-glycoprotein in ovarian cancer: a molecular marker associated with multidrug resistance. J. Clin. Oncol. 1985, 3, 311-315.
13. Ma, D. D.; Scurr, R. D.; Davey, R. A.; Mackertich, S. M.; Harman, D. H.; et al. Detection of a multidrug resistant phenotype in acute non-lymphoblastic leukaemia. Lancet 1987, 1, 135-137.
14. van de Vrie, W.; Marquet, R. L.; Stoter, G.; De Bruijn, E. A.; Eggermont, A. M. In vivo model systems in P-glycoprotein-mediated multidrug resistance. Crit. Rev. Clin. Lab Sci. 1998, 35, 1-57.
15. Trock, B. J.; Leonessa, F.; Clarke, R. Multidrug resistance in breast cancer: a meta-analysis of MDR1/gp170 expression and its possible functional significance. J. Natl. Cancer Inst. 1997, 89, 917-931.
16. Nooter, K.; Westerman, A. M.; Flens, M. J.; Zaman, G. J.; Scheper, R. J. ; et al. Expression of the multidrug resistance-associated protein (MRP) gene in human cancers. Clin. Cancer Res. 1995, 1, 1301-1310.
17. Abbaszadegan, M. R.; Futscher, B. W.; Klimecki, W. T.; List, A.; Dalton, W. S. Analysis of multidrug resistance-associated protein (MRP) messenger RNA in normal and malignant hematopoietic cells. Cancer Res. 1994, 54, 4676-4679.
18. Schneider, E.; Cowan, K. H.; Bader, H.; Toomey, S.; Schwartz, G. N.; et al. Increased expression of the multidrug resistance-associated protein gene in relapsed acute leukemia. Blood 1995, 85, 186-193.
19. Thomas, G. A.; Barrand, M. A.; Stewart, S.; Rabbitts, P. H.; Williams, E. D.; et al. Expression of the multidrug resistance-associated protein (MRP) gene in human lung tumours and normal tissue as determined by in situ hybridisation. Eur. J. Cancer 1994, 30A, 1705-1709.
20. Schadendorf, D.; Makki, A.; Stahr, C.; van Dyck, A.; Wanner, R.; et al. Membrane transport proteins associated with drug resistance expressed in human melanoma. Am. J. Pathol. 1995, 147, 1545-1552.
21. Hart, S. M.; Ganeshaguru, K.; Hoffbrand, A. V.; Prentice, H. G.; Mehta, A. B. Expression of the multidrug resistance-associated protein (MRP) in acute leukaemia. Leukemia 1994, 8, 2163-2168.
22. Leveille-Webster, C. R.; Arias, I. M. The biology of the P-glycoproteins. J. Membr. Biol. 1995, 143, 89-102.
23. Robert, J.; Jarry, C. Multidrug resistance reversal agents. J. Med. Chem. 2003, 46, 4805-4817.
24. Tsuruo, T.; Iida, H.; Tsukagoshi, S.; Y., S. Overcoming of vincristine resistance in P388 leukaemia in vivo and in vitro through enhanced cytotoxicity of vincristine and vinblastine by verapamil. Cancer Res. 1981, 41, 1967-1972.
25. Kaye, S. B. Multidrug resistance: clinical relevance in solid tumours and strategies for circumvention. Curr. Opin. Oncol. 1998, 10 Suppl 1, S15-19.
26. Sikic, B. I. Modulation of multidrug resistance: a paradigm for translational clinical research. Oncology (Huntingt) 1999, 13, 183-187.
27. Endicott, J. A.; Ling, V. The biochemistry of P-glycoprotein-mediated multidrug resistance. Annu. Rev. Biochem. 1989, 58, 137-171.
28. Zaman, G. J.; Versantvoort, C. H.; Smit, J. J.; Eijdems, E. W.; de Haas, M.; et al. Analysis of the expression of MRP, the gene for a new putative transmembrane drug transporter, in human multidrug resistant lung cancer cell lines. Cancer Res. 1993, 53, 1747-1750.
29. Burger, H.; Nooter, K.; Sonneveld, P.; Van Wingerden, K. E.; Zaman, G. J.; et al. High expression of the multidrug resistance-associated protein (MRP) in chronic and prolymphocytic leukaemia. Br. J. Haematol. 1994, 88, 348-356.
30. Lawrence, D. S.; Copper, J. E.; Smith, C. D. Structure-activity studies of substituted quinoxalinones as multiple-drug-resistance antagonists. J. Med. Chem. 2001, 44, 594-601.
31. Smith, C. D. Azabicyclooctane compositions and methods for enhancing chemotherapy. US Patent 6,248,752, 2001.
32. Smith, C. D.; Myers, C. B.; Zilfou, J. T.; Smith, S. N.; Lawrence, D. S. Indoloquinoxaline compounds that selectively antagonize P-glycoprotein. Oncol. Res. 2001, 12, 219-229.
33. Martin, C.; Berridge, G.; Mistry, P.; Higgins, C.; Charlton, P.; et al. The molecular interaction of the high affinity reversal agent XR9576 with P-glycoprotein. Br. J. Pharmacol. 1999, 128, 403-411.
34. Stewart, A.; Steiner, J.; Mellows, G.; Laguda, B.; Norris, D.; et al. Phase I trial of XR9576 in healthy volunteers demonstrates modulation of P-glycoprotein in CD56+ lymphocytes after oral and intravenous administration. Clin. Cancer Res. 2000, 6, 4186-4191.
35. Dantzig, A. H.; Shepard, R. L.; Cao, J.; Law, K. L.; Ehlhardt, W. J.; et al. Reversal of P-glycoprotein-mediated multidrug resistance by a potent cyclopropyldibenzosuberane modulator, LY335979. Cancer Res. 1996, 56, 4171-4179.
36. Roe, M.; Folkes, A.; Ashworth, P.; Brumwell, J.; Chima, L.; et al. Reversal of P-glycoprotein mediated multidrug resistance by novel anthranilamide derivatives. Bioorg. Med. Chem. Lett. 1999, 9, 595-600.
37. Newman, M. J.; Rodarte, J. C.; Benbatoul, K. D.; Romano, S. J.; Zhang, C.; et al. Discovery and characterization of OC144-093, a novel inhibitor of P-glycoprotein-mediated multidrug resistance. Cancer Res. 2000, 60, 2964-2972.
38. Smith, C. D.; Zilfou, J. T.; Stratmann, K.; Patterson, G. M.; Moore, R. E. Welwitindolinone analogues that reverse P-glycoprotein-mediated multiple drug resistance. Mol. Pharmacol. 1995, 47, 241-247.
39. Fairchild, C. R.; Ivy, S. P.; Kao-Shan, C. S.; Whang-Peng, J.; Rosen, N. ; et al. Isolation of amplified and overexpressed DNA sequences from adriamycin-resistant human breast cancer cells. Cancer Res. 1987, 47, 5141-5148.
40. Schneider, E.; Horton, J. K.; Yang, C. H.; Nakagawa, M.; Cowan, K. H. Multidrug resistance-associated protein gene overexpression and reduced drug sensitivity of topoisomerase II in a human breast carcinoma MCF7 cell line selected for etoposide resistance. Cancer Res. 1994, 54, 152-158.
41. Lee, B. D.; French, K. J.; Zhuang, Y.; Smith, C. D. Development of a syngeneic in vivo tumor model and its use in evaluating a novel P-glycoprotein modulator, PGP-4008. Oncol. Res. 2003, 14, 49-60.
42. Watanabe, T.; Tsuge, H.; Oh-Hara, T.; Naito, M.; Tsuruo, T. Comparative study on reversal efficacy of SDZ PSC 833, cyclosporin A and verapamil on multidrug resistance in vitro and in vivo. Acta Oncol. 1995, 34, 235-241.
43. Saito, T.; Zhang, Z. J.; Tokuriki, M.; Ohtsubo, T.; Shibamori, Y.; et al. Cyclosporin A inhibits the extrusion pump function of p-glycoprotein in the inner ear of mice treated with vinblastine and doxorubicin. Brain Res. 2001, 901, 265-270.
44. Still, W. C. K., M.; Mitra, A. Rapid chromatographic techniques for preparative separation with moderate resolution. J. Org. Chem. 1978, 43, 2923-2924.
45. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 1990, 82, 1107-1112.