N-methylation of anthracyclines modulates their cytotoxicity and pharmacokinetic in wild type and multidrug resistant cells

Biomedicine and Pharmacotherapy

Volumn 57, Issue 7, 2003, Pages 301-308

  Gate, L ^a,b   Couvreur, P ^a   Nguyen Ba, G ^a   Tapiero, H ^a  

^a UNIV PARIS SUD   (France)

^b FOX CHASE CANCER CENTER   (United States)

Author keywords

Circumvention; Multidrug resistance; New anthracyclines

Indexed keywords

ANTHRACYCLINE DERIVATIVE; DOXORUBICIN; GLYCOPROTEIN P; OXAUNOMYCIN; VERAPAMIL;

ARTICLE; CANCER CHEMOTHERAPY; CYTOTOXICITY; DRUG ACCUMULATION; DRUG TRANSPORT; LEUKEMIA CELL; METHYLATION; MULTIDRUG RESISTANCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION; WILD TYPE;

EID: 0141448860     PISSN: 07533322     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0753-3322(03)00037-4     Document Type: Article

References (33)

1. Gewirtz D.A. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem Pharmacol. 57:1999;727-741.
2. Batist G., Tulpule A., Sinha B.K., Katki A.G., Myers C.E., Cowan K.H. Overexpression of a novel anionic glutathione transferase in multidrug-resistant human breast cancer cells. J Biol Chem. 261:1986; 15544-15549.
3. Ikegawa T., Ohtani H., Koyabu N., Juichi M., Iwase Y., Ito C., et al. Inhibition of P-glycoprotein by flavonoid derivatives in adriamycin-resistant human myelogenous leukemia (K562/ADM) cells. Cancer Lett. 177:2002;89-93.
4. Tapiero H., Munck J.N., Fourcade A., Lampidis T.J. Cross-resistance to rhodamine 123 in Adriamycin- and daunorubicin-resistant Friend leukemia cell variants. Cancer Res. 44:1984;5544-5549.
5. Gianni L. Anthracycline resistance: the problem and its current definition. Semin Oncol. 24:1997;S10-S17.
6. Tewey K.M., Rowe T.C., Yang L., Halligan B.D., Liu L.F. Adriamycin-induced DNA damage mediated by mammalian DNA topoisomerase II. Science. 226:1984;466-468.
7. Willmore E., Errington F., Tilby M.J., Austin C.A. Formation and longevity of idarubicin-induced DNA topoisomerase II cleavable complexes in K562 human leukaemia cells. Biochem Pharmacol. 63:2002;1807-1815.
8. Spoelstra E.C., Westerhoff H.V., Pinedo H.M., Dekker H., Lankelma J. The multidrug-resistance-reverser verapamil interferes with cellular P-glycoprotein-mediated pumping of daunorubicin as a non-competing substrate. Eur J Biochem. 221:1994;363-373.
9. Nielsen D., Maare C., Skovsgaard T. Cellular resistance to anthracyclines. Gen Pharmacol. 27:1996;251-255.
10. Lampidis T.J., Kolonias D., Podona T., Israel M., Safa A.R., Lothstein L., et al. Circumvention of P-GP MDR as a function of anthracycline lipophilicity and charge. Biochemistry. 36:1997;2679-2685.
11. Mariani M., Capolongo L., Suarato A., Bargiotti A., Mongelli N., Grandi M., et al. Growth-inhibitory properties of novel anthracyclines in human leukemic cell lines expressing either Pgp-MDR or at-MDR. Invest New Drugs. 12:1994;93-97.
12. Lampidis T.J., Shi Y.F., Calderon C.L., Kolonias D., Tapiero H., Savaraj N. Accumulation of simple organic cations correlates with differential cytotoxicity in multidrug-resistant and -sensitive human and rodent cells. Leukemia. 11:1997;1156-1159.
13. Schaefer A., Westendorf J., Lingelbach K., Schmidt C.A., Mihalache D.L., Reymann A., et al. Decreased resistance to N,N-dimethylated anthracyclines in multidrug-resistant Friend erythroleukemia cells. Cancer Chemother Pharmacol. 31:1993;301-307.
14. Consoli U., Priebe W., Ling Y.H., Mahadevia R., Griffin M., Zhao S., et al. The novel anthracycline annamycin is not affected by P-glycoprotein-related multidrug resistance: comparison with idarubicin and doxorubicin in HL-60 leukemia cell lines. Blood. 88:1996;633-644.
15. Tapiero H., Boule D., Trincal G., Fourcade A., Lampidis T.J. Potentiation of adriamycin accumulation and effectiveness in adriamycin-resistant cells by aclacinomycin A. Leuk Res. 12:1988;411-418.
16. Tapiero H., Fourcade A., Munck J.N., Zwingelstein G., Lampidis T.J. Cellular pharmacology of anthracycline resistance and its circumvention. Drugs Exp Clin Res. 12:1986;265-273.
17. Lampidis T.J., Munck J.N., Krishan A., Tapiero H. Reversal of resistance to rhodamine 123 in adriamycin-resistant Friend leukemia cells. Cancer Res. 45:1985;2626-2631.
18. Germann U.A., Gottesman M.M., Pastan I. Expression of a multidrug resistance-adenosine deaminase fusion gene. J Biol Chem. 264:1989;7418-7424.
19. Pastan I., Gottesman M.M., Ueda K., Lovelace E., Rutherford A.V., Willingham M.C. A retrovirus carrying an MDR1 cDNA confers multidrug resistance and polarized expression of P-glycoprotein in MDCK cells. Proc Natl Acad Sci USA. 85:1988;4486-4490.
20. Broxterman H.J., Kuiper C.M., Schuurhuis G.J., Tsuruo T., Pinedo H.M., Lankelma J. Increase of daunorubicin and vincristine accumulation in multidrug resistant human ovarian carcinoma cells by a monoclonal antibody reacting with P-glycoprotein. Biochem Pharmacol. 37:1988;2389-2393.
21. Egorin M.J., Clawson R.E., Ross L.A., Bachur N.R. Cellular pharmacology of N,N-dimethyl daunorubicin and N,N-dimethyl adriamycin. Cancer Res. 40:1980;1928-1933.
22. Tapiero H., Nguyen-Ba G., Lampidis T.J. Cross resistance relevance of the chemical structure of different anthracyclines in multidrug resistant cells. Pathol Biol (Paris). 42:1994;328-337.
23. Burke T.G., Tritton T.R. Location and dynamics of anthracyclines bound to unilamellar phosphatidylcholine vesicles. Biochemistry. 24:1985;5972-5980.
24. Burke T.G., Israel M., Seshadri R., Doroshow J.H. A fluorescence study examining how 14-valerate side chain substitution modulates anthracycline binding to small unilamellar phospholipid vesicles. Biochim Biophys Acta. 982:1989;123-130.
25. Dupou-Cezanne L., Sautereau A.M., Tocanne J.F. Localization of adriamycin in model and natural membranes. Influence of lipid molecular packing. Eur J Biochem. 181:1989;695-702.
26. Gallois L., Fiallo M., Laigle A., Priebe W., Garnier-Suillerot A. The overall partitioning of anthracyclines into phosphatidyl-containing model membranes depends neither on the drug charge nor the presence of anionic phospholipids. Eur J Biochem. 241:1996;879-887.
27. Burke T.G., Morin M.J., Sartorelli A.C., Lane P.E., Tritton T.R. Function of the anthracycline amino group in cellular transport and cytotoxicity. Mol Pharmacol. 31:1987;552-556.
28. Kolonias D., Podona T., Savaraj N., Gate L., Cossum P., Lampidis T.J. Comparison of annamycin to adriamycin in cardiac and MDR tumor cell systems. Anticancer Res. 19:1999;1277-1283.
29. Bain L.J., LeBlanc G.A. Interaction of structurally diverse pesticides with the human MDR1 gene product P-glycoprotein. Toxicol Appl Pharmacol. 141:1996;288-298.
30. Friche E., Danks M.K., Beck W.T. Characterization of tumor cell resistance to 4′-deoxy-4′-iododoxorubicin developed in Ehrlich ascites cells in vivo. Cancer Res. 52:1992;5701-5706.
31. Davies S.M., Robson C.N., Davies S.L., Hickson I.D. Nuclear topoisomerase II levels correlate with the sensitivity of mammalian cells to intercalating agents and epipodophyllotoxins. J Biol Chem. 263:1988;17724-17729.
32. Patel S., Sprung A.U., Keller B.A., Heaton V.J., Fisher L.M. Identification of yeast DNA topoisomerase II mutants resistant to the antitumor drug doxorubicin: implications for the mechanisms of doxorubicin action and cytotoxicity. Mol Pharmacol. 52:1997;658-666.
33. Schisselbauer J.C., Crescimanno M., D'Alessandro N., Clapper M., Toulmond S., Tapiero H., et al. Glutathione, glutathione S-transferases, and related redox enzymes in Adriamycin-resistant cell lines with a multidrug resistant phenotype. Cancer Commun. 1:1989;133-139.