The use of Tris-lipidation to modify drug cytotoxicity in multidrug resistant cells expressing P-glycoprotein or MRP1

British Journal of Pharmacology

Volumn 137, Issue 8, 2002, Pages 1280-1286

  Davey, Ross A ^a   Davey, Mary W ^b   Cullen, Karen V ^b   Wells, Xanthe E ^c   Francis, Craig L ^c   Williams, Hua Ming ^c   Yang, Qi ^c   Moghaddam, Minoo J ^c   Widmer, Fred ^c   Whittaker, Robert G ^c  

^a ROYAL NORTH SHORE HOSPITAL   (Australia)

^b UNIVERSITY OF TECHNOLOGY SYDNEY   (Australia)

^c CSIRO   (Australia)

Author keywords

AZT; Chlorambucil; Drug modification; Leukaemia cells; Methotrexate; MRP1; Multidrug resistance; P glycoprotein; Tris Lipidation

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTINEOPLASTIC AGENT; CHLORAMBUCIL; CHLORAMBUCIL GLYCINE DIPALMITATE; CHLORAMBUCIL GLYCINE TRIPALMITATE; CHLORAMBUCIL GLYCINE TRIS MONOPALMITATE; GLYCOPROTEIN P; METHOTREXATE DERIVATIVE; METHOTREXATE GLYCINE DIPALMITATE; METHOTREXATE GLYCINE TRIPALMITATE; METHOTREXATE GLYCINE TRIS MONOPALMIATE; MULTIDRUG RESISTANCE PROTEIN 1; PALMITIC ACID; UNCLASSIFIED DRUG; ZIDOVUDINE DERIVATIVE; ZIDOVUDINE GLYCINE DIPALMITATE; ZIDOVUDINE GLYCINE TRIPALMITATE; ZIDOVUDINE GLYCINE TRIS MONOPALMITATE;

ARTICLE; CELL LINE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DERIVATIZATION; DRUG CYTOTOXICITY; DRUG SENSITIVITY; HUMAN; HUMAN CELL; LIPOPHILICITY; MULTIDRUG RESISTANCE; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANTINEOPLASTIC AGENTS; BIOLOGICAL TRANSPORT; BUFFERS; CELL SURVIVAL; CHEMISTRY, PHARMACEUTICAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG RESISTANCE, MULTIPLE; HUMANS; LIPID METABOLISM; LIPIDS; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS; P-GLYCOPROTEIN; TROMETHAMINE; TUMOR CELLS, CULTURED;

EID: 0036945260     PISSN: 00071188     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.bjp.0704983     Document Type: Article

References (29)

1. Bakos, E., Evers, R., Sinko, E., Varadi, A., Borst, P. & Sakadi, B. (2000). Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol. Pharmacol., 57, 760-768.
2. Bebawy, M., Morris, M.B. & Roufogalis, B.D. (1999). A continuous fluorescence assay for the study of p-glycoprotein-mediated drug efflux using inside-out membrane vesicles. Analyt. Biochem., 268, 270-277.
3. Beck, W., Mueller, T. & Tanzer, L. (1979). Altered surface membrane glycoproteins in vinca alkaloid-resistant human leukemic lymphoblasts. Cancer Res., 39, 2070-2076.
4. Bender, V.J., Cameron, F.H., Hendry, P., Lockett, T.J. & Whittaker, R.G. (1994). Delivery studies using peptide-fatty acid conjugates. In Peptides. Chemistry, Structure and Biology. ed. Hodges, R.S. and Smith, J.A. pp. 327-328, Leiden: ESCOM.
5. Borst, P., Evers, R., Kool, M. & Wijnholds, J. (2000). A family of drug transporters: The multidrug resistance-associated proteins. J. Natl. Cancer. Inst., 92, 1295-1302.
6. Cameron, F.H., Moghaddam, M.J., Bender, V.J., Whittaker, R.G. & Lockett, T.L. (1999). A transfection compound series based on a versatile tris linkage. Biochim. Biophy. Acta, 1417, 37-50.
7. Cole, S.P., Bhardwaj, G., Gerlach, J.H., Mackie, J.E., Grant, C.E., Almquist, K.C., Stewart, A.J., Kurz, E.U., Duncan, A.M. & Deeley, R.G. (1992). Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science, 258, 1650-1654.
8. Czernecki, S. & Valery, J.M. (1991). An efficient synthesis of 3′-azido-3′-deoxythymidine (AZT). Synthesis, March 1991, 239-240.
9. Davey, M.W., Hargrave, R.M. & Davey, R.A. (1996). Comparison of drug accumulation in P-glycoprotein-expressing and MRP-expressing human leukaemia cells. Leuk. Res., 20, 657-664.
10. Davey, R.A., Longhurst, T.J., Davey, M.W., Belov, L., Harvie, R.M., Hancox, D. & Wheeler, H. (1995). Drug resistance mechanisms and MRP expression in response to epirubicin treatment in a human leukaemia cell line. Leuk. Res., 19, 275-282.
11. Davey, R.A., Su, G.M., Hargrave, R.M., Harvie, R.M., Baguley, B.C. & Davey, M.W. (1997). The potential of n-[2-(dimethylamino)ethyl]acridine-4-carboxamide to circumvent three multidrug-resistance phenotypes in vitro. Cancer Chemother. Pharmacol., 39, 424-430.
12. De Graaf, D., Sharma, R.C., Mechetner, E.B., Schimke, R.T. & Roninson, I.B. (1996). P-glycoprotein confers methotrexate resistance in 3T6 ceils with deficient carrier-mediated methotrexate uptake. Proc. Natl. Acad. Sci., 93, 1238-1242.
13. Efferth, T., Davey, M., Olbrich, A., Rucker, G., Gerbhart, E. & Davey, R. (2002). Activity of drugs from Traditional Chinese Medicine towards sensitive and MDR1- or MRP1-overexpressing multidrug-resistant human CCRF-CEM leukemia cells. Blood Cells Mol. Dis., 28, 160-168.
14. Endicott, J.A & Ling, V. (1989). The biochemistry of P-glycoprotein-mediated multidrug resistance. Annu. Rev. Biochem., 58, 137-171.
15. Foley, G, Lazarus, H., Faber, S., Geren-Uzman, B., Boone, A.B. & McCarthy, R.E. (1965). Continuous culture of human lymphoblast from peripheral blood of a child with acute leukemia. Cancer, 18, 156-192.
16. Gifford, A.J., Kavallaris, M., Madafiglio, J., Matherly, L.H., Stewart, B.W., Haber, M. & Norris, M.D. (1998). P-glycoprotein-mediated methotrexate resistance in CCRF-CEM sublines deficient in methotrexate accumulation due to point mutation in the reduced folate carrier gene. Int. J. Cancer, 78, 176-181.
17. Goldstein, L.J., Pastan, I. & Gottesman, M.M. (1992). Multidrug resistance in human cancer. Crit. Rev. Oncol. Hematol., 12, 243-253.
18. Grech, K.V., Davey, R.A. & Davey, M.W. (1998). The relationship between modulation of MDR and glutathione in MRP-overexpressing human leukemia cells. Bioehem. Pharmacol., 55, 1283-1289.
19. Hooijberg, J.H., Broxterman, H.J., Kool, M., Assaraf, Y.G., Peters, G.J., Noordhuis, P., Scheper, R.J., Borst, P., Pinedo, H.M. & Jansen, G. (1999). Antifolate resistance mediated by the multidrug resistance proteins MRP1 and MRP2. Cancer Res., 59, 2532-2535.
20. Lampidis, T.J., Kolonias, D., Podona, T., Israel, M., Safa, A.R., Lothstein, L., Savaraj, N., Tapiero, H. & Priebe, W. (1997). Circumvention of P-gp MDR as a function of anthrocyline lipophilicity and charge. Biochem., 36, 2679-2685.
21. Marks, D.C., Belov, L., Davey, M.W., Davey, R.A. & Kidman, A.D. (1992). The MTT cell viability assay for cytotoxicity testing in multidrug-resistant human leukemic cells. Leuk. Res., 16, 1165-1173.
22. Reilly, W.G., Whittaker, R.G., Jennings, P.A. & Finney, K.G. (1991). Self adjuvanting peptide vaccine delivery system and production thereof. Patent PTC/AU92/O0377. Flied 26.7.91.
23. Rosowsky, A., Forsch, R., Uren, J. & Wick, M. (1981). Methotrexate analogues. 14. Synthesis of new gamma-substituted derivatives as dihydrofolate reductase inhibitiors and potential anticancer agents. J. Med. Chem., 24, 1450-1455.
24. Walker, C., Walton, C.E., Petkovich, J.M., Moghaddam, M.J., Wells, X.E. & Whittaker, R.G. (2000). Tris-Lipid technology creates a novel adjuvant. Proceedings of 30th Annual Conference of the Australasian Society for Immunology, Sydney, poster 10.20.
25. Wells, X.E., Bender, V.J., Francis, C.L., He-Williams, H.M., Manthey, M.K., Moghaddam, M.J., Reilly, W.G. & Whittaker, R.G. (1999). Tris and the ready production of drug-fatty acyl conjugates. Drug Dev. Res., 46, 302-308.
26. Whittaker, R.G. & Bender, V.B. (1992). A new procedure for coupling peptides with fats. In Innovations and Perspectives in Solid Phase Synthesis. Collected Papers. Second International Symposium. Epton, R. ed. pp. 495-498. Andover, UK: Intercept Limited.
27. Whittaker, R.G., Bender, V.J., Reilly, W.G. & Moghaddam, M.J. (1995). Improved therapeutic agents. Patent PTC/AU96/0015. Filed 16.1.95.
28. Whittaker, R.G., Hayes, P.J. & Bender, V.J. (1993). A gentle method for linking Tris to amino acids and peptides. Peptide Res., 6, 125-128.
29. Whittaker, R., Wells, X. & Reilly, W. (1999). Methotrexate Derivatives. Patent PCT/AU99/01073.