Photoaffinity analogs for multidrug resistance-related transporters and their use in identifying chemosensitizers

Drug Resistance Updates

Volumn 2, Issue 6, 1999, Pages 371-381

  Safa, Ahmad R ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; AZIDOPAMIL; AZIDOPINE; AZIRIDINE; COLCHICINE; CYCLOSPORIN; DACTINOMYCIN; DAUNORUBICIN; DOXORUBICIN; FORSKOLIN DERIVATIVE; GLYCOPROTEIN P; IODINE 125; LEUKOTRIENE C4; MULTIDRUG RESISTANCE PROTEIN; PACLITAXEL; TAMOXIFEN; TRITIUM; VINBLASTINE DERIVATIVE; VINCRISTINE;

CANCER; CANCER CELL; CANCER RESISTANCE; DRUG BINDING SITE; DRUG PROTEIN BINDING; GENE OVEREXPRESSION; LABELING INDEX; MULTIDRUG RESISTANCE; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; PROTEIN TARGETING; REVIEW;

EID: 0033495305     PISSN: 13687646     EISSN: None     Source Type: Journal    
DOI: 10.1054/drup.1999.0105     Document Type: Article

References (79)

1. Gottesman M. M., Pastan I., Ambudkar S. V. P-glycoprotein and multidrug resistance. Curr Opin Genet Dev. 6:1996;610-617.
2. Cole S. P., Deely R. G. Multidrug resistance mediated by the ATP-binding cassette transporter protein MRP. Bioessays. 20:1998;931-940.
3. 4and structurally related conjugates. J Biol Chem. 269:1994;27807-27810.
4. Jedlitschky G., Leier I., Bucholz U., Barnouin K., Kurtz G., Keppler D. Transport of glutathione, glucuronate, and sulfate conjugates by the MRP gene-encoded conjugate export pump. Cancer Res. 56:1996;988-994.
5. Zaman G. J., Cnubben N. H., van Bladeren P. J., Evers R., Borst P. Transport of the glutathione conjugate of ethacrynic acid by the human multidrug resistance protein MRP. FEBS Lett. 391:1996;126-130.
6. Ishikawa T. The ATP-dependent glutathione S-conjugate export pump. Trends Biochem Sci. 17:1992;463-468.
7. Oude Elferink R. P., Meijer D. K., Kuipers F., Jansen P. L., Groen A. K., Groothuis G. M. Hepatobiliary secretion of organic compounds; molecular mechanisms of membrane transport. Biochim Biophys Acta. 1241:1995;215-268.
8. Keppler D., Leier I., Jedlitschky G., Konig J. ATP-dependent transport of glutathione S-conjugates by the multidrug resistance protein MRP1 and its apical isoform MRP2. Chem Biol Interact. 111-112:1998;153-161.
9. Hooijberg J. H., Broxterman H. J., Kool M. Antifolate resistance mediated by the multidrug resistance proteins MRP1 and MRP2. Cancer Res. 59:1999;2532-2535.
10. Kool M., van der Linden M., de Haas M., Baas F., Borst P. Expression of human MRP6, a homologue of the multidrug resistance protein gene MRP1, in tissues and cancer cells. Cancer Res. 59:1999;175-182.
11. Kool M., van der Linden M., de Haas M. MRP3, an organic anion transporter able to transport anti-cancer drugs. Proc Natl Acad Sci USA. 96:1999;6914-6919.
12. Germann U. A., Ford P. J., Shlyakhter D., Mason V. S., Harding M. W. Chemosensitization and drug accumulation effects of VS-710, verapamil, cyclosporin A, MS-209 and GF120918 in multidrug resistant HL60/ADR cells expressing the multidrug resistance-associated protein MRP. Anticancer Drugs. 8:1997;141-155.
13. Fedan J. S., Hogaboom G. K., O'Donnell J. P. Photoaffinity labels as pharmacological tools. Biochem Pharmacol. 33:1984;1167-1180.
14. Bayley H., Knowles J. R. Photoaffinity labeling. Methods Enzymol. 46:1977;69-114.
15. Cavalla D., Neff N. H. Chemical mechanisms for photoaffinity labeling of receptors. Biochem Pharmacol. 34:1985;2821-2826.
16. Safa A. R. Photoaffinity labeling of P-glycoprotein in multidrug-resistant cells [corrected and republished article originally printed in Cancer Invest 1992; 10: 295-305. Cancer Invest. 11:1993;46-56.
17. Safa A. R. Photoaffinity labels for characterizing drug interaction of P-glycoprotein. Methods Enzymol. 292:1998;289-307.
18. Safa A. R., Glover C. J., Meyers M. B., Biedler J. L., Felsted R. L. Vinblastine photoaffinity labeling of a high molecular weight surface membrane glycoprotein specific for multidrug-resistant cells. J Biol Chem. 261:1986;6137-6140.
19. Beck W. T., Cirtain M. C., Glover C. J., Felsted R. L., Safa A. R. Effects of indole alkaloids on multidrug resistance and labeling of P-glycoprotein by a photoaffinity analog of vinblastine. Biochem Biophys Res Commun. 153:1988;959-966.
20. Safa A. R., Stern R. K., Choi K. Molecular basis of preferential resistance to colchicine in multidrug-resistant human cells conferred by Gly-185 to Val-185 substitution in P-glycoprotein. Proc Natl Acad Sci USA. 87:1990;7225-7229.
21. Cornwell M. M., Safa A. R., Felsted R. L., Gottesman M. M., Pastan I. Membrane vesicles from multidrug-resistant human cancer cells contain a specific 150- to 170-kDa protein detected by photoaffinity labeling. Proc Natl Acad Sci USA. 83:1986;3847-3850.
22. Safa A., Schilsky R. L. Multidrug-resistance. Principles of Antineoplastic Drug Development and Pharmacology. 1996;Marcel Dekker Inc., New York. p. p.
23. Busche R., Tummler B., Riordan J. R., Cano-Gauci D. F. Preparation and utility of a radioiodinated analogue of daunomycin in the study of multidrug resistance. Mol Pharmacol. 35:1989;414-421.
24. Beck W. T., Qian X. D. Photoaffinity substrates for P-glycoprotein. Biochem Pharmacol. 43:1992;89-93.
25. Felsted R. L., Glover C. J., Clawson R. E., Averbuch S. D. Rat heart anthracycline-binding polypeptides identified by photoaffinity labeling. Mol Pharmacol. 30:1986;388-397.
26. 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. 162:1989;1402-1408.
27. Nare B., Lui Z., Prichard R. K., Georges E. Benzimidazoles, potent anti-mitotic dugs: substrates for the P-glycoprotein transporter in multidrug-resistant cells. Biochem Pharmacol. 48:1994;2215-2222.
28. Nare B., Prichard R. K., Georges E. Characterization of rhodamine 123 binding to P-glycoprotein in human multidrug-resistant cells. Mol Pharmacol. 45:1994;1145-1152.
29. Wu Q., Bounaud P. Y., Kuduk S. D. Identification of the domains of photoincorporation of the 3′- and 7-benzophenone analogues of taxol in the carboxyl-terminal half of murine mdr1b P-glycoprotein. Biochemistry. 37:1998;11272-11279.
30. Ojima I., Bounaud P. Y., Ahern D. G. New photoaffinity analogs of paclitaxel. Bioorg Med Chem Lett. 9:1999;1189-1194.
31. Safa A. R., Glover C. J., Sewell J. L., Meyers M. B., Biedler J. L., Felsted R. L. Identification of the multidrug resistance-related membrane glycoprotein as an acceptor for calcium channel blockers. J Biol Chem. 262:1987;7884-7888.
32. Safa A. R. Photoaffinity labeling of the multidrug-resistance-related P-glycoprotein with photoactive analogs of verapamil. Proc Natl Acad Sci USA. 85:1988;7187-7191.
33. Qian X. D., Beck W. T. Binding of an optically pure photoaffinity analogue of verapamil, LU-49888, to P-glycoprotein from multidrug-resistant human leukemic cell lines. Cancer Res. 50:1990;1132-1137.
34. Borchers C., Ulrich W. R., Klemm K. B9209-005, an azido derivative of the chemosensitizer dexniguldipine-HCl, photolabels P-glycoprotein. Mol Pharmacol. 48:1995;21-29.
35. 125I]arylazidoprazosin binds to a specific peptide of P-glycoprotein in multidrug-resistant cells. Biochem Biophys Res Commun. 166:1990;259-266.
36. 125I]iodophenethyl)-spiperone binds to specific regions of P-glycoprotein and another multidrug binding protein, spiperophilin, in human neuroblastoma cells. Biochemistry. 33:1994;256-265.
37. Akiyama S., Yoshimura A., Kikuchi H., Sumizawa T., Kuwano M., Tahara Y. Synthetic isoprenoid photoaffinity labeling of P-glycoprotein specific to multidrug-resistant cells. Mol Pharmacol. 36:1989;730-735.
38. Foxwell B. M., Mackie A., Ling V., Ryffel B. Identification of the multidrug resistance-related P-glycoprotein as a cyclosporine binding protein. Mol Pharmacol. 36:1989;543-546.
39. Morris D. I., Speicher L. A., Ruoho A. E., Tew K. D., Seamon K. B. Interaction of forskolin with the P-glycoprotein multidrug transporter. Biochemistry. 30:1991;8371-8379.
40. Speicher L. A., Barone L. R., Chapman A. E. P-glycoprotein binding and modulation of the multidrug-resistant phenotype by estramustine. J Natl Cancer Inst. 86:1994;688-694.
41. Qian X. D., Beck W. T. Progesterone photoaffinity labels P-glycoprotein in multidrug-resistant human leukemic lymphoblasts. J Biol Chem. 265:1990;18753-18756.
42. Wolf D. C., Horwitz S. B. P-glycoprotein transports corticosterone and is photoaffinity-labeled by the steroid. Int J Cancer. 52:1992;141-146.
43. Safa A., Roberts S., Agresti M., Fine R. Tamoxifen aziridine, a novel photoaffinity probe for P-glycoprotein in multidrug resistant cells. Biochem Biophys Res Commun. 202:1994;606-612.
44. Bruggemann E. P., Currier S. J., Gottesman M. M., Pastan I. Characterization of the azidopine and vinblastine binding site of P-glycoprotein. J Biol Chem. 267:1992;21020-21026.
45. Greenberger L. M. Major photoaffinity drug labeling sites for iodoaryl azidoprazosin in P-glycoprotein are within, or immediately C-terminal to, transmembrane domains 6 and 12. J Biol Chem. 268:1993;11417-11425.
46. Morris D. I., Greenberger L. M., Bruggemann E. P. Localization of the forskolin labeling sites to both halves of P-glycoprotein: similarity of the sites labeled by forskolin and prazosin. Mol Pharmacol. 46:1994;329-337.
47. Demmer A., Thole H., Kubesch P. Localization of the iodomycin binding site in hamster P-glycoprotein. J Biol Chem. 272:1997;20913-20919.
48. Tamai I., Safa A. R. Azidopine noncompetitively interacts with vinblastine and cyclosporin A binding to P-glycoprotein in multidrug resistant cells. J Biol Chem. 266:1991;16796-167800.
49. Tamai I., Safa A. R. Competitive interaction of cyclosporins with the Vinca alkaloid binding site of P-glycoprotein in multidrug-resistant cells. J Biol Chem. 265:1990;16509-16513.
50. Chen G., Duran G. E., Steger K. A. Multidrug-resistant human sarcoma cells with a mutant P-glycoprotein, altered phenotype, and resistance to cyclosporins. J Biol Chem. 272:1997;5974-5982.
51. Sonveaux N., Vigano C., Shapiro A. B., Ling V., Ruysschaert J. M. Ligand-mediated tertiary structure changes of reconstituted P-glycoprotein. A tryptophan fluorescence quenching analysis. J Biol Chem. 274:1999;17649-17654.
52. Devine S. E., Ling V., Melera P. W. Amino acid substitutions in the sixth transmembrane domain of P-glycoprotein alter multidrug resistance. Proc Natl Acad Sci U S A. 89:1992;4564-4568.
53. Kajiji S., Talbot F., Grizzuti K. Functional analysis of P-glycoprotein mutants identifies predicted transmembrane domain 11 as a putative drug binding site. Biochemistry. 32:1993;4185-4194.
54. Loo T. W., Clarke D. M. Merck Frosst Award Lecture 1998. Molecular dissection of the human multidrug resistance P-glycoprotein. Biochem Cell Biol. 77:1999;11-23.
55. Hafkemeyer P., Dey S., Ambudkar S. V., Hrycyna C. A., Pastan I., Gottesman M. M. Contribution to substrate specificity and transport of nonconserved residues in transmembrane domain 12 of human P-glycoprotein. Biochemistry. 37:1998;16400-16409.
56. Ferry D. R., Russell M. A., Cullen M. H. P-glycoprotein possesses a 1,4-dihydropyridine-selective drug acceptor site which is allosterically coupled to aVinca -alkaloid-selective binding site. Biochem Biophys Res Commun. 188:1992;440-445.
57. Ayesh S., Shao Y. M., Stein W. D. Co-operative competitive and non-competitive interactions between modulators of P-glycoprotein. Biochim Biophys Acta. 1316:1996;8-18.
58. Shao Y. M., Ayesh S., Stein W. D. Mutually co-operative interactions between modulators of P-glycoprotein. Biochim Biophys Acta. 1360:1997;30-38.
59. Boer R., Dichtl M., Borchers C. Reversible labeling of a chemosensitizer binding domain of P-glycoprotein with a novel 1,4-dihydropyridine drug transport inhibitor. Biochemistry. 35:1996;1387-1396.
60. Garrigos M., Mir L. M., Orlowski S. Competitive and non-competitive inhibition of the multidrug-resistance-associated P-glycoprotein ATPase-further experimental evidence for a multisite model. Eur J Biochem. 244:1997;664-673.
61. Fleming G. F., Amato J. M., Agresti M., Safa A. R. Megestrol acetate reverses multidrug resistance and interacts with P-glycoprotein. Cancer Chemother Pharmacol. 29:1992;445-449.
62. Shapiro A. B., Fox K., Lam P., Ling V. Stimulation of P-glycoprotein-mediated drug transport by prazosin and progesterone. Evidence for a third drug-binding site. Eur J Biochem. 259:1999;841-850.
63. Borgnia M. J., Eytan G. D., Assaraf Y. G. Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 271:1996;3163-3171.
64. DiDiodato G., Sharom F. J. Interaction of combinations of drugs, chemosensitizers and peptides with the P-glycoprotein multidrug transporter. Biochem Pharmacol. 53:1997;1789-1797.
65. Stein W. D. Kinetics of the P-glycoprotein, the multidrug transporter. Exp Physiol. 83:1998;221-232.
66. Sikic B. I. Pharmacologic approaches to reversing multidrug resistance. Semin Hematol. 34:1997;40-47.
67. 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. 39:1999;36.
68. Lampidis T. D., Kolonias D., Podona M. Circumvention of P-gp MDR as a function of anthracycline lipophilicity and charge. Biochemistry. 36:1997;2679-2685.
69. Marbeuf-Gueye C., Broxterman H. J., Dubru F., Priebe W., Garnier-Suillerot A. Kinetics of anthracycline efflux from multidrug resistance protein-expressing cancer cells compared with P-glycoprotein-expressing cancer cells. Mol. Pharmacol. 53:1998;141-147.
70. Polizzi D., Pratesi G., Tortoreto M. A novel taxane with improved tolerability and therapeutic activity in a panel of human tumor xenografts. Cancer Res. 59:1999;1036-1040.
71. McGrath T., Latoud C., Arnold S. T., Safa A. R., Felsted R. L., Center M. S. Mechanisms of multidrug resistance in HL60 cells. Analysis of resistance associated membrane proteins and levels of mdr gene expression. Biochem Pharmacol. 38:1989;3611-3619.
72. Gekeler V., Ise W., Sanders H., Ulrich W. R., Beck J. The leukotriene LTD4 receptor antagonist MK571 specifically modulates MRP associated multidrug resistance. Biochem Biophys Res Commun. 208:1995;345-352.
73. Ciaccio P. J., Shen H., Kruh G. D., Tew K. D. Effects of chronic ethacrynic acid exposure on glutathione conjugation and MRP expression in human colon tumor cells. Biochem Biophys Res Commun. 222:1996;111-115.
74. Vezmar M., Deady L. W., Tilley L., Georges E. The quinoline-based drug, N-[4-[1-hydroxy-2-(dibutylamino) ethyl]quionlin-8-yl]-4-azidosalicylamide, photoaffinity labels the multidrug resistance protein (MRP) at a biologically relevant site. Biochem Biophys Res Commun. 241:1997;104-111.
75. Vezmar M., Georges E. Direct binding of chloroquine to the multidrug resistance protein (MRP): possible role for MRP in chloroquine drug transport and resistance in tumor cells. Biochem Pharmacol. 56:1998;733-742.
76. Germann U. A., Shlyakhter D., Mason V. S. Cellular and biochemical characterization of VX-710 as a chemosensitizer: reversal of P-glycoprotein mediated multidrug resistance in vitro. Anticancer Drugs. 8:1997;125-140.
77. Yanagisawa T., Newman A., Coley H., Renshaw J., Pinkerton C. R., Pritchard-Jones K. BIRIDOCAR (VX-710; Incel): an effective chemosensitizer in neuroblastoma. Br J Cancer. 80:1999;1190-1196.
78. Romsicki Y., Sharom F. J. The membrane lipid environment modulates drug interactions with the P-glycoprotein multidrug transporter. Biochemistry. 38:1999;6887-6896.
79. Safa A. Identification and characterization of the drug-binding sites of P-glycoprotein. Gupta S., Tsuruo T T. Multidrug Resistance in Cancer Cells. 1996;John Wiley & Sons, New York.