Requirements for P-glycoprotein recognition based on structure-activity relationships in the podophyllotoxin series

Anti-Cancer Drug Design

Volumn 13, Issue 4, 1998, Pages 317-336

  Etievant, Chantal ^a   Schambel, Philippe ^a   Guminski, Yves ^a   Barret, Jean Marc ^a   Imbert, Thierry ^a   Hill, Bridget T ^a  

^a INSTITUT DE RECHERCHE PIERRE FABRE   (France)

Author keywords

Molecular modeling; Multidrug resistance; P glycoprotein recognition; Podophyllotoxin derivatives; Structure activity relationships

Indexed keywords

ANTINEOPLASTIC AGENT; EPIPODOPHYLLOTOXIN; GLYCOPROTEIN P; PODOPHYLLOTOXIN DERIVATIVE; TUBULIN; UNINDEXED DRUG;

ANIMAL CELL; ARTICLE; BINDING SITE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; LEUKEMIA P 388; MICROTUBULE ASSEMBLY; MOUSE; MULTIDRUG RESISTANCE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; MICE; MICROTUBULE PROTEINS; MODELS, MOLECULAR; P-GLYCOPROTEIN; PODOPHYLLOTOXIN; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUMOR CELLS, CULTURED;

ANIMALIA; MURINAE;

EID: 0031778539     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. CONTER, F. & BECK, W.T (1984). Acquisition of multiple drug resistance by CCRF-CEM cells selected for different degrees of resistance to vincristine. Cancer Trestment Report, 68, 831.
2. CORTESE, F., BHATTACHARYYA, B. & WOLFF, J (1977). Podophyllotoxin as a probe for the colchicine binding site of tubulin. The Journal of Biological Chemistry, 252, 1134.
3. EYMIN, B., SOLARY, E., CHEVILLARD, S., DUBREZ, L., GOLDWASSER, F., DUCHANP, O., GENNE, P., LETEUTRE, F & POMMIER, Y. (1995). Cellular pharmacology of azatoxins (topoisomerase-II and tubulin inhibitors) in P-glycoprotein-positive and -negative cell lines. International Journal of Cancer, 63, 268.
4. FORD, JM. (1996). Experimental reversal of P-glycoprotein-mediated multidrug resistance by pharmacological chemosensitisers. European Journal of Cancer, 32A, 991.
5. FORD, J M. &. HAIT, W.N. (1993). Pharmacologic circumvention of multidrug resistance. Cytotechnology, 12, 171.
6. GASKIN, F., CANTOR, C.R. & SHELANSKI, M (1974). Turbidimetric studies of the in vitro assembly and disassembly of porcine neurotubules. Journal of Molecular Biology, 89, 737.
7. GERMANN, U.A. (1996). P-glycoprotein - a mediator of multidrug resistance in tumour cells European Journal of Cancer, 32A, 927.
8. GERMANN, U.A. & HARDING, M.W. (1995). Chemosensitizers to overcome and prevent multidrug resistance? Journal of the National Cancer Institute, 87, 1573.
9. GOTTESMAN, M.M. & PASTAN, I (1993). Biochemistry of multidrug resistance mediated by the multidrug transporter. Annual Review of Biochemistry, 62, 385.
10. HAAR, E. TER, ROSENKRANZ, H.S., HAMEL, E. & DAY, W.D. (1996). Computationnal and molecular modeling evaluation of the structural basis for tubulin polymerization inhibition by colchicine site agents. Bioorganic & Medicinal Chemistry, 4, 1659.
11. HAMEL, E. (1990). Interactions of tubulin with small ligands. In Microtubule Proteins. Avila, J. (ed.), p. 89. CRC Press: Boca Raton, FL.
12. HANSEN, H.F., JENSEN, R.B., WILLUMSEN, A.M., NØRSKOV-LAURITSEN, N., EBBESEN, P., NIELSEN, P.E. & BUCHARDT, O. (1993). New podophyllotoxin and congeners: synthesis, structure elucidation and biological testing. Acta Chemica Scandinavica, 47, 1190.
13. HILL, B T (1993). Differing patterns of cross-resistance resulting from exposure to specific antitumour drugs or to radiation in vitro. Cytotechnology, 12, 265.
14. HILL, B.T. & HOSKING, L K. (1994). Differential effectiveness of a range of novel drug-resistance modulators, relative to verapamil, in influencing vinblastine or teniposide cytotoxicity in human lymphoblastoid CCRF-CEM sublines expressing classic or atypical multidrug resistance. Cancer Chemotherapy and Pharmacology, 33, 317.
15. JOHNSON, R.K., CHITNIS, M.P., EMBREY, W.M. & GREGORY, E.B. (1978). In vivo characteristics of resistance and cross-resistance of an adriamycin-resistant subline of P388 leukemia. Cancer Treatment Report, 62, 1535.
16. KAMATH, N., GRABOWSKI, D., FORD, J, KERRIGAN, D., POMMIER, Y. & GANAPATHI, R. (1992). Overexpression of P-glycoprotein and alterations in topoisomerase II in P388 mouse leukemia cells selected in vivo for resistance to mitoxantrone. Biochemical Pharmacology, 44, 937.
17. KUHN, M., KELLER-JULSEN, C. & VON WARTBURG, A (1969). Mitosis-inhibiting natural substances. XXII. Partial synthesis of 4′-demethylepipodophyllotoxin. Helvetica Chimica Acta, 52, 944.
18. LOIKE, J.D., BREWER, C.F., STERNLICHT, H., GENSLER, W.J. & HORWITZ, S. (1978). Structure activity study of the inhibition of microtubule assembly in vitro by podophyllotoxin and its congeners. Cancer Research, 38, 2688.
19. MARQUARDT, D. & CENTER. M.S. (1992). Drug transport mechanisms in HL60 cells isolated for resistance to Adriamycin: evidence for nuclear drug accumulation and redistribution in resistant cells. Cancer Research, 52, 3157.
20. MCGOWN, A.T. & FOX, B.W. (1990). Differential cytotoxicity of Combretastatins A1 and A4 in two daunorubicin-resistant P388 cell lines. Cancer Chemotherapy and Pharmacology, 26, 79.
21. MOSMANN, T. (1983). Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65, 55.
22. PASTAN, I & GOTTESMAN, M.M. (1991). Multidrug resistance. Annual Review of Medicine, 42, 277.
23. PINEDO, H.M. (1996). Drug resistance, illustration of the complexity of translational research. Steiner Award Lecture. International Journal of Cancer, 65, 561.
24. 1H-NMR assignment of podophyllotoxin. Journal of Natural Products, 52, 1290.
25. SACKETT, D.L. (1993). Podophyllotoxin, steganacin and combretastatin: natural products that bind at the colchicine site of tubulin. Pharmacological Therapeutics, 59, 163.
26. SAFA, A.R., STERN, R.K., CHOI, K., AGRESTI, M., TAMAI, I., MEHTA, N.D & RONINSON, I.B. (1990). Molecular basis of preferential resistance to colchicine in multidrug-resistant human cells conferred by Gly-185 → Val-185 substitution in P-glycoprotein. Proceedings of the National Academy of Science, USA, 87, 7225.
27. SUZUKI, T, FUKAZAWA, N &. SAN-NOHE, K. (1997). Structure-activity relashionship of newly synthesized quinoline derivatives for reversal of multidrug resistance in cancer. Journal of Medicinal Chemistry, 40, 2047.
28. TANG-WAI, D F., BROSSI, A., ARNOLD, L.D & GROS, P. (1993). The nitrogen of the acetamido group of colchicine modulates P-glycoprotein-mediated multidrug resistance. Biochemistry, 32, 6470.
29. TANG-WAI, D.F., BROSSI, A., ARNOLD, L.D. & GROS, P. (1994). Structure activity relationships in the colchicine molecule with respect to interaction with the mammalian multidrug transporter, P-glycoprotein. Heterocycles, 39, 385.
30. TSURUO, T., IIDA, H., TSUKAGOSHI, S. & SAKURAI, Y. (1981). Overcoming of vincristine resistance in P388 leukemia in vivo and in vitro through enhanced cytotoxicity of vincristine and vinblastine by verapamil. Cancer Research, 41, 1967.