Design of new drug molecules to be used in reversing multidrug resistance in cancer cells

Current Cancer Drug Targets

Volumn 9, Issue 3, 2009, Pages 298-306

  Mayur, Y C ^a   Peters, G J ^b   Rajendra Prasad, V V S ^a   Lemos, C ^b,c   Sathish, N K ^a  

^a V L COLLEGE OF PHARMACY   (India)

^b VU UNIVERSITY MEDICAL CENTER   (Netherlands)

^c University of Porto   (Portugal)

Author keywords

Acridones; Calmodulin; Multidrug resistance (MDR); Multiple resistant protein (MRP); P glycoprotein (P gp)

Indexed keywords

1,3 BIS(9 OXOACRIDIN 10 YL)PROPANE; ACRIDONE DERIVATIVE; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; BIRICODAR; CALCIUM CHANNEL BLOCKING AGENT; CALMODULIN INHIBITOR; CAMPTOTHECIN; CISPLATIN; CYCLOSPORIN A; CYTARABINE; DAUNORUBICIN; DOCETAXEL; ELACRIDAR; ETOPOSIDE; FLUOROURACIL; FOLIC ACID ANTAGONIST; IMIDAZOACRIDONE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; LANIQUIDAR; MERCAPTOPURINE; PROTEIN KINASE C INHIBITOR; QUININE; SURFACTANT; TARIQUIDAR; TIOGUANINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALSPODAR; VINBLASTINE; VINCRISTINE; ZOSUQUIDAR;

ACUTE GRANULOCYTIC LEUKEMIA; ARTICLE; BINDING SITE; CANCER RESISTANCE; CLINICAL TRIAL; DRUG BINDING; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG TARGETING; HUMAN; LUNG NON SMALL CELL CANCER; MULTIDRUG RESISTANCE; STRUCTURE ACTIVITY RELATION; TREATMENT FAILURE; UNSPECIFIED SIDE EFFECT;

ACRIDONES; ANTINEOPLASTIC AGENTS; ATP-BINDING CASSETTE TRANSPORTERS; DRUG DESIGN; DRUG RESISTANCE, MULTIPLE; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; NEOPLASMS; P-GLYCOPROTEIN;

EID: 65649121136     PISSN: 15680096     EISSN: None     Source Type: Journal    
DOI: 10.2174/156800909788166619     Document Type: Article

References (74)

1. Kane, S. E. Multidrug resistance of cancer cells: In advances in drug research; Academic Press: New York, 1996, pp. 181-252.
2. Mitscher, L. A.; Pillai, S. P.; Gentry, E. J.; Shankel, D. M. Multidrug resistance. Med. Res. Rev. 1999, 19, 477-496.
3. Bosch, I.; Croop, J. P-glycoprotein multidrug resistance and cancer. Biochim. Biophys. Acta 1996, 1288, F37-F54. (Pubitemid 26335491)
4. Volm, M.; Mattern, J. Resistance mechanisms and their regulation in lung cancer. J. Crit. Rev. Oncogenesis 1996, 7, 224-227.
5. Van Veen, H. W.; Konings, W. N. The ABC family of multidrug transporters in microorganisms. Biochim. Biophys. Acta 1998, 1365, 31-36. (Pubitemid 29359235)
6. Hrycyna, C. A.; Gottesman, M. M. Multidrug ABC transporter from bacteria to man: An emerging hypothesis for the universality of molecular mechanisms and functions. Drug Resist. Updat. 1998, 1, 81-83.
7. Hooijberg, J. H.; De Vries, N. A.; Kaspers, G. J. L.; Pieters, R.; Jansen, G.; Peters, G. J. Multidrug resistance proteins and folate supplementation: therapeutic implications for antifolates and other classes of drugs in cancer treatment. Cancer Chem. Pharm. 2006, 58, 1-12.
8. Avendana, C.; Menendez, J. C. Recent advances in multidrug resistance modulators. Med. Chem. Rev. Online 2004, 1, 419-444.
9. Teodri, E.; Dei, S.; Scapecchi.; Gualtieri, F. The medicinal chemistry of multidrug resistance agents. IL Farmaco. 2002, 57, 385-415.
10. Avendano, C.; Menendez, J. C. Inhibitors of multidrug resistance to antitumor agents. Curr. Med. Chem. 2002, 9, 159-193. (Pubitemid 34436440)
11. Robert, J.; Jarry, C. Multidrug drug reversal agents. J. Med. Chem. 2003, 46, 4805-4817.
12. Endicott, J. A.; Ling, V. The biochemistry of P-glycoprotein-mediated multidrug resistance. Annu. Rev. Biochem. 1989, 58, 137-171. (Pubitemid 19172967)
13. Higgins, C. E. ABC transporters: From microorganisms to man. Ann. Rev. Cell. Biol. 1992, 8, 67-113. (Pubitemid 23000992)
14. Gottesman, M. M.; Pastan, I. Biochemistry of multidrug resistance mediated by multidrug transporter. Annu. Rev. Biochem. 1993, 62, 385-427. (Pubitemid 23237876)
15. Gottesman, M. M.; Fojo, T.; Bates S. E. Multidrug resistance in cancer: role of ATP-dependent transporters. Nat. Rev. Cancer 2002, 2, 48-58. (Pubitemid 37328807)
16. List, A. F.; Spier, C.; Greer, J.; Wolff, S.; Hutter, J.; Dorr, R.; Salmon, S.; Futscher, B.; Baier, M.; Dalton, W. Phase I/II trial of cyclosporine as a chemotherapy-resistance modifier in acute leukemia. Blood 2001, 98, 3212-3220.
17. Thomas, H.; Coley, H. M. Overcoming Multidrug Resistance in Cancer. An Update on the Clinical Strategy of Inhibiting P-Glycoprotein. Cancer Control 2003, 10, 159-165. (Pubitemid 36437822)
18. Chan., H. S.; Haddad, G.; Thorner, G. P-Glycoprotein Expression as a Predictor of the Outcome of Therapy for Neuroblastoma. N. Eng. J. Med. 1991, 325, 1608-1614.
19. List, A. F.; Kopecky, K. J.; Willman, C. L.; Head, D. R.; Persons, D. L.; Slovak, M. L.; Dorr, R.; Karanes, C.; Hynes, H. E.; Doroshow, J. H.; Muhammad, S.; Appelbaum, F. R. Benefit of cyclosporine modulation of drug resistance in patients with poor-risk acute myeloid leukemia: a Southwest Oncology Group study. Blood 2001, 98, 3212-3220.
20. Wattel, E.; Solary, E.; Hecquet, B.; Caillot, D.; Ifrah, N.; Brion, A.; Milpied, N.; Janvier, M.; Guerci, A.; Rochant, H.; Cordonnier, C.; Dreyfus, F.; Veil, A.; Hoang-Ngoc, L.; Stoppa, A. M.; Gratecos, N.; Sadoun, A.; Tilly, H.; Brice, P.; Lioure, B.; Desablens, B.; Pignon, B.; Abgrall, J. P.; Leporrier, M.; Fenaux, P. Quinine improves results of intensive chemotherapy (IC) in myelodysplastic syndromes (MDS) expressing P-glycoprotein (PGP). Updated results of a randomized study. Groupe Français des Myélodysplasies (GFM) and Groupe GOELAMS. Adv. Exp. Med. Biol. 1999, 457, 35-46.
21. Daenen, S.; van der Holt, B.; Verhoef, G. E. G.; Löwenberg, B.; Wijermans, P. W.; Huijgens, P. C.; Rien van Marwijk, K.; Schouten, H. C.; Kramer, M. H. H.; Ferrant, A.; van den Berg, E.; Steijaert, M. M.; Verdonck, L. F.; Sonneveld, P. Addition of cyclosporin A to the combination of mitoxantrone and etoposide to overcome resistance to chemotherapy in refractory or relapsing acute myeloid leukaemia; a randomized phase II trial from HOVON, the Dutch-Belgian Haemato-Oncology Working Group for adults. Leuk. Res. 2004, 28, 1057-1067. (Pubitemid 39037339)
22. Hollt, V.; Kouba, M.; Dietel, M.; Vogt, G. Stereoisomers of calcium antagonists which differ markedly in their potencies as calcium blockers are equally effective in modulating drug transport by Pglycoprotein. Biochem. Pharmacol. 1992, 43, 2601-2608.
23. Goldman, B. Multidrug resistance: can new drugs help chemotherapy score against cancer? J. Natl. CancerInst. 2003, 95, 255-257. (Pubitemid 36336473)
24. Product Development Pipeline - November 2004 [online]. 〈http://www.glaxosmithkline.de/content/forschung/pipeline-dec2004. pdf〉 (2004)
25. Guns, E. S.; Denyssevych, T.; Dixon, R.; Bally, M. B.; Mayer, L. Drug interaction studies between paclitaxel (Taxol) and OC144-093 - a new modulator of MDR in cancer chemotherapy. Eur. J. Drug Metab. Pharmacokinet. 2002, 27, 119-126. (Pubitemid 34594896)
26. Minderman, H.; O'Loughlin, K. L.; Pendyala, L.; Baer, M. R. VX-710 (biricodar) increases drug retention and enhances chemosensitivity in resistant cells overexpressing P-glycoprotein, multidrug resistance protein, and breast cancer resistance protein. Clin. Cancer Res. 2004, 10, 1826-1834. (Pubitemid 38435574)
27. Xenova Group Limited Tariquidar [online], 〈http://www.xenova.co.uk/ dc-xr9576.html〉, 2006.
28. van Zuylen, L.; Nooter, K.; Sparreboom, A.; Verweij, J. Development of multidrug- resistance convertors: sense or nonsense? Invest. New Drugs 2000, 18, 205-220. (Pubitemid 30599141)
29. Dantzig, A. H.; de Alwis, D. P.; Burgess, M. Considerations in the design and development of transport inhibitors as adjuncts to drug therapy. Adv. Drug Deliv. Rev. 2003, 55, 133-150. (Pubitemid 36078455)
30. Loo, T. W.; Clarke, D. M. Blockage of drug resistance in vitro by disulfiram, a drug used to treat alcoholism. J. Natl. Cancer Inst. 2000, 92, 898-902. (Pubitemid 30429189)
31. Seelig, A.; Gatlik-Landwojtowicz, E. Inhibitors of multidrug efflux transporters: their membrane and protein interactions. Mini Rev. Med. Chem. 2005, 5, 135-151. (Pubitemid 40305726)
32. Pleban, K.; Ecker, G. F. Inhibitors of p-glycoprotein lead identification and optimisation. Mini Rev. Med. Chem. 2005, 5, 153-163. (Pubitemid 40305727)
33. Michael, J. P. Representative pyrimidine derivatives synthesized using the described quinazoline and acridone alkaloids. Nat. Prod. Rep. 2005, 22, 627-646.
34. Wallstab, A.; Koester, M.; Bohme, M.; Keppler, D. Selective inhibition of MDR1 P-glycoprotein-mediated transport by the acridone carboxamide derivative GG918. Br. J. Cancer 1999, 79, 1053.
35. Traunecker, H. C. L.; Stevens, M. C. G.; Kerr, D. J.; Ferry, D. R. The acridone carboxamide GF120918 potently reverses P-glycoprotein- mediated resistance in human sarcoma MES-Dx5 cells. Br. J. Cancer 1999, 81, 942-951. (Pubitemid 29516136)
36. Evers, R.; Kool, M.; Smith, A. J.; van Deemter, L.; de Haas, M.; Borst, P. Inhibitory effect of the reversal agents V-104, GF120928 and pluronic L61 on Pgp-, MRP1- and MRP2 mediated transport. Br. J. Cancer 2000, 83, 366-374. (Pubitemid 30453578)
37. Krishnegowda, G.; Thimmaiah, P.; Hegde, R.; Dass, C.; Houghton, P. J.; Thimmaiah, K. N. Synthesis and chemical characterization of 2-methoxy-N(10)- substituted acridones needed to reverse vinblastine resistance in multidrug resistant (MDR) cancer cells. Bioorg. Med. Chem. 2002, 10, 2367-2380. (Pubitemid 34450926)
38. Wieslaw, M. C.; Sante, M.; Jolanta, P.L.; Konopa, J. 5-[(Aminoalkyl) amino] imidazo[4,5,1-de]acridin-6-ones as a novel class of antineoplastic agents J. Med. Chem. 1990, 33, 49-52.
39. Horton, J. K.; Thimmaiah, K. N.; Altenberg, H. A.; Castro, A. F.; Germain, G. S.; Gowda, G. K.; Houghton, P. J. Characterisation of a novel bisacridone and comparison with PSC 833 as a potent and poorly reversible modulator of glycoprotein. Mol. Pharmacol. 1997, 52, 948-957. (Pubitemid 28013712)
40. Hegde, R.; Thimmaiah, P.; Mayur, Y. C.; Krishnegowda, G.; Thimmaiah, K. N.; Houghton, P. J. Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells. Eur. J. Med. Chem. 2004, 39, 161-177. (Pubitemid 38249529)
41. Mayur, Y. C.; Padma, T.; Parimala, B. H.; Chandramouli, K. H.; Jagadeesh, S.; Gowda, N. M.; Thimmaiah, K. N. Sensitization of multidrug resistant (MDR) cancer cells to vinblastine by novel acridones: correlation between anti-calmodulin activity and anti-MDR activity. Med. Chem. 2006, 2, 63-77. (Pubitemid 44083167)
42. 10-Substituted Acridones as Reversers of Multidrug Resistance in Cancer Cells. Lett. Drug Des. Discov. 2007, 4, 327-335.
43. Boumendjel, A.; Macalou, A.; Ahmed-Belkacem, A.; Blanc, M.; Pietro, A. D. Acridone derivatives: Design, synthesis, and inhibition of breast cancer resistance protein ABCG2. Bioorg. Med. Chem. 2007, 15, 2892-2897. (Pubitemid 46402973)
44. Mayur Y. C.; Jagadeesh S.; Thimmaiah, K. N. Targeting calmodulin in reversing multidrug resistance in cancer Mini Rev. Med. Chem. 2006, 6, 1383-1389.
45. Hegewisch-Becker S. MDR1 reversal: criteria for clinical trials designed to overcome the multidrug resistance phenotype. Leukemia 1996, 10, S32-S38.
46. Zamora, J. M.; Pearse, H. L.; Beck, W. T. Physical-chemical properties shared by compounds that modulate multidrug resistance in human leukemic cells. Mol. Pharmacol. 1988, 33, 454-462.
47. Stouch, T. R.; Gudmundsson, A. Progress in understanding the structure-activity relationships of P-glycoprotein. Adv. Drug Deliv. Rev. 2002, 54, 315-328. (Pubitemid 34260956)
48. Wiese, M.; Pajeva, I. K. Structure-activity relationships of multidrug resistance reversers. Curr. Med. Chem. 2001, 8, 685-713. (Pubitemid 32409800)
49. Seelig, A. A general pattern for substrate recognition by P-glycoprotein. Eur. J. Biochem. 1998, 251, 252-261. (Pubitemid 28081437)
50. Loo, T. W.; Clarke, D. M. Inhibition of oxidative cross-linking between engineered cysteine residues at positions 332 in predicted transmembrane segment (TM) 6 and 975 in predicted TM12 of human P-glycoprotein by drug substrates. J. Biol. Chem. 1996, 271, 27482-27487. (Pubitemid 26367309)
51. Loo, T. W.; Clarke, D. M. Identification of residues within the drug-binding domain of the human multidrug resistance p-glycoprotein by cysteine-scanning mutagenesis and reaction with dibromobimane. J. Biol. Chem. 2000, 275, 39272-39278. (Pubitemid 32058947)
52. Loo, T. W.; Clarke, D. M. Defining the drug-binding site in the human multidrug resistance P-glycoprotein using a methanesulfonate analog of verapamil, MTS-verapamil. J. Biol. Chem. 2001, 276, 14972-14979. (Pubitemid 37373379)
53. Loo, T. W.; Clarke, D. M. Location of the rhodamine-binding site in the human multidrug resistance P-glycoprotein. J. Biol. Chem. 2002, 277, 44332-44338. (Pubitemid 36157868)
54. Scala, S.; Akhmed, N.; Rao, U. S.; Paull, K.; Lan, L. B.; Dickstein, B.; Lee J. S.; et al. P-glycoprotein substrates and antagonists cluster into two distinct groups. Mol. Pharmacol. 1997, 51, 1024-1033. (Pubitemid 27249136)
55. Seelig, A.; Landwojtowicz, E. Structure-activity relationship of P-glycoprotein substrates and modifiers. Eur. J. Pharm. Sci. 2000, 12, 31-40. (Pubitemid 30061573)
56. Klopman, G.; Shi, L. M.; Ramu, A. Quantitative structureactivity relationship of multidrug resistance reversal agents. Mol. Pharmacol. 1997, 52, 323-334. (Pubitemid 27349625)
57. Bakken, G. A.; Jurs, P. C. Classification of multidrug-resistance reversal agents using structure-based descriptors and linear discriminant analysis. J. Med. Chem. 2000, 43, 4534-4541. (Pubitemid 32046878)
58. Ekins, S.; Kim, R. B.; Leake, B. F.; Dantzig, A. H.; Schuetz, E. G.; Lan, L. B.; Yasuda, K.; Shepard, R. L.; Winter, M. A.; Schuetz, J. D.; Wikel, J. H.; Wrighton, S. A. Three-dimensional quantitative structure activity relationships of inhibitors of P-glycoprotein. Mol. Pharmacol. 2002, 61, 964-973. (Pubitemid 34441760)
59. Pajeva, I. K.; Wiese, M. Pharmacophore model of drugs involved in P- glycoprotein multidrug resistance: explanation of structural variety (hypothesis). J. Med. Chem. 2002, 45, 5671-5686. (Pubitemid 35453760)
60. Safa, A. R. Photoaffinity labeling of the multidrug-resistance related P- glycoprotein with photoactive analogs of verapamil. Proc. Natl. Acad. Sci. USA 1988, 85, 7187-7191. (Pubitemid 18241850)
61. Safa, A. R.; Mehta, N. D.; Agresti, M. Photoaffinity labeling of P-glycoprotein in multidrug resistant cells with photoactive analogs of colchicine. Biochem. Biophys. Res. Commun. 1989, 162, 1402-1408. (Pubitemid 19214739)
62. Bruggemann, E. P.; Germann, U. A.; Gottesmann, M. M.; Pastan, I. Two different regions of P-glycoprotein are photoaffinitylabeled by azidopine. J. Biol. Chem. 1989, 264, 15483-15488. (Pubitemid 19242924)
63. Demmer, A.; Thole, H.; Kubesch, P.; Brandt, T.; Raida, M.; Fislage, R.; Tummler, B.Localization of the iodomycin binding site in hamster P- glycoprotein. J. Biol. Chem. 1997, 272, 20913-20919. (Pubitemid 27355663)
64. Dreenberger, L. M. Major photoaffinity drug labeling sites for iodoaryl azidoprazosin in P-glycoprotein are within, or immediately C-terminal to, transmembrane domain-6 and domain- 12. J. Biol. Chem. 1993, 268, 11417-11425. (Pubitemid 23162341)
65. Morris, D. I.; Greenberger, L. M.; Bruggemann, E. P.; Cardarelli, C.; Gottesman, M. M.; Pastan, I.; Seamon, K. B. Localization of the forskolin labeling sites to both halves of P-glycoprotein: similarity of the sites labeled by forskolin and prazosin. Mol. Pharmacol. 1994, 46, 329-337. (Pubitemid 24271429)
66. 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. (Pubitemid 29222564)
67. Loo, T. W.; Clarke, D. M. Molecular dissection of the human Multidrug resistance P-glycoprotein. Biochem. Cell. Biol. 1999, 77, 11-23. (Pubitemid 29342829)
68. Shapiro, A. B.; Ling, V. Positively cooperative sites for drug transport by P- glycoprotein with distinct drug specificities. Eur. J. Biochem. 1997, 250, 130-137. (Pubitemid 27504592)
69. Pascaud, C.; Garrigos, M.; Orlowski, S. Multidrug resistance transporter P- glycoprotein has distinct but interacting binding sites for cytotoxic drugs and reversing agents. Biochem. J. 1998, 333, 351-358. (Pubitemid 28379536)
70. Garrigues, A.; Loiseau, N.; Delaforge, M.; Ferte, J.; Garrigos, M.; Andre, F.; Orlowski, S. Characterization of two pharmacophores on the Multidrug transporter P-glycoprotein. Mol. Pharmacol. 2002, 62, 1288-1298. (Pubitemid 35403824)
71. Loo, T. W.; Clarke, D. M. The packing of the transmembrane segments of human multidrug resistance P-glycoprotein is revealed by disulfide cross linking analysis. J. Biol. Chem. 2000, 275, 5253-5256. (Pubitemid 30115151)
72. Loo, T. W.; Clarke, D. M. Drug-stimulated ATPase activity of human P- glycoprotein is blocked by disulfide cross-linking between the nucleotide- binding sites. J. Biol. Chem. 2000, 275, 19435-19438. (Pubitemid 30441531)
73. Loo, T. W.; Clarke, D. M. Determining the dimensions of the drug-binding domain of human P-glycoprotein using thiol crosslinking compounds as molecular rulers. J. Biol. Chem. 2001, 276, 36877-36880. (Pubitemid 37384096)
74. Senior, A. E. Catalytic mechanism of P-glycoprotein. Acta Physiol. Scand. 1998, 163, 213-218. (Pubitemid 28439420)