A novel non-natural nucleoside that influences P-glycoprotein activity and mediates drug resistance

Biochemistry

Volumn 49, Issue 8, 2010, Pages 1640-1648

  Eng, Kevin T ^a   Berdis, Anthony J ^a  

^a CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

, INHIBITOR; ATP BINDING CASSETTE TRANSPORTERS; ATP-ASE ACTIVITY; CANCER CHEMOTHERAPY; CATALYTIC EFFICIENCIES; CHEMOTHERAPEUTIC AGENTS; CONTEMPORARY MODELS; CORE STRUCTURE; DRUG RESISTANCE; IN-VITRO; MULTIDRUG RESISTANCE; OVER-EXPRESSION; P-GLYCOPROTEIN; POTENTIAL DRUG; THERAPEUTIC AGENTS;

CHEMOTHERAPY; GLYCOPROTEINS; MONOLAYERS;

DRUG INTERACTIONS;

5 CYCLOHEXYLINDOLYL 2' DEOXYRIBOSE; ADENOSINE; ADENOSINE TRIPHOSPHATASE; ADENOSINE TRIPHOSPHATE; DEOXYRIBOSE; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; NUCLEOSIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CATALYSIS; CONTROLLED STUDY; CYTOTOXICITY; ENZYME ACTIVITY; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN STRUCTURE;

ADENOSINE TRIPHOSPHATASES; ANIMALS; CELL LINE; CELL LINE, TUMOR; CELL SURVIVAL; DEOXYRIBOSE; DOGS; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; ENZYME ACTIVATION; HUMANS; KINETICS; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; NUCLEOSIDES; P-GLYCOPROTEIN;

EID: 77749304795     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi9020428     Document Type: Article

References (33)

1. Gottesman, M. M., and Ling, V. (2006) The molecular basis of multidrug resistance in cancer: The early years of P-glycoprotein research. FEBS Lett. 580, 998-1009.
2. Juliano, R. L., and Ling, V. (1976) A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim. Bionhvs. Acta 455, 152-162.
3. Ling, V., Kartner, N., Sudo, T., Siminovitch, L., and Riordan, J. R. (1983) Multidrug-resistance phenotype in Chinese hamster ovary cells. Cancer Treat. Rep. 67, 869-874. (Pubitemid 14231377)
4. Eckford, P. D., and Sharom, F. J. (2009) ABC efflux pump-based resistance to chemotherapy drugs. Chem. Rev. 109, 2989-3011.
5. Penson, R. T., Oliva, E., Skates, S. J., Glyptis, T., Fuller, A. F., Jr., Goodman, A., and Seiden, M. V. (2004) Expression of multidrug resistance-1 protein inversely correlates with paclitaxel response and survival in ovarian cancer patients: A study in serial samples. Gvnecol. Qncol. 93, 98-106. (Pubitemid 38429555)
6. Szakacs, G., Paterson, J. K., Ludwig, J. A., Booth-Genthe, C., and Gottesman, M. M. (2006) Targeting multidrug resistance in cancer. Nat. Rev. Drug Discovery 5, 219-234.
7. Higgins, C. F., Hiles, I. D., Salmond, G. P., Gill, D. R., Downie, J. A., Evans, I. J., Holland, I. B., Gray, L., Buckel, S. D., and Bell, A. W. et al. (1986) A family of related ATP-binding subunits coupled to many distinct biological processes in bacteria. Nature 323, 448-450.
8. Higgins, C. F., and Linton, K. J. (2004) The ATP switch model for ABC transporters, Nat. Struct. Mol. Biol. 11, 918-926.
9. Sauna, Z. E., and Ambudkar, S. V. (2007) About a switch: How P-glycoprotein (ABCBl) harnesses the energy of ATP binding and hydrolysis to do mechanical work. Mol Cancer Ther. 6, 13-23.
10. Higgins, C. F., and Gottesman, M. M. (1992) Is the multidrug transporter a flippase? Trends Biochem. Sci. 17,18-21.
11. Aller, S. G., Yu, J., Ward, A., Weng, Y., Chittaboina, S., Zhuo, R., Harrell, P. M., Trinh, Y. T., Zhang, Q., Urbatsch, I. L., and Chang, G. (2009) Structure of P-glycoprotein reveals a molecular basis for polyspecific drug binding. Science 323,1718-1722.
12. Germann, U. A., Shlyakhter, D., Mason, V. S., Zelle, R. E., Duffy, J. P., Galullo, V., Armistead, D. M., Saunders, J. O., Boger, J., and Harding, M. W. (1997) Cellular and biochemical characterization of VX-71.0 as a chemosensitizer: Reversal of P-glycoprotein-mediated multidrug resistance in vitro. Anticancer Drugs 8, 125-140.
13. Dhainaut, A., Regnier, G., Atassi, G., Pierre, A., Leonce, S., KrausBerthier, L., and Prost, J. F. (1992) New triazine derivatives as potent modulators of multidrug resistance. J. Med. Chem. 35, 2481-2496.
14. McDevitt, C. A., and Callaghan, R. (2007) How can we best use structural information on P-glycoprotein to design inhibitors? pharmacol. Ther.113, 429-441.
15. Schindler, T., Bornmann, W., Pellícena, P., Miller, W. T., Clarkson, B., and Kuriyan, J. (2000) Structural mechanism for STI-571 inhibition of abelson tyrosine kinase. Science 289,1938-1942.
16. Martin, C., Berridge, G., Mistry, P., Higgins, C., Charlton, P., and Callaghan, R. (1999) The molecular interaction of the high affinity reversal agent XR9576 with P-glycoprotein. Br. J. Pharmacol. 128, 403-411. (Pubitemid 29458600)
17. Fox, E., and Bates, S. E. (2007) Tariquidar (XR9576): A P-glycoprotein drug efflux pump inhibitor. Expert Rev. Anticancer Ther. 7,447459. (Pubitemid 46681800)
18. Eng, K., Scouten-Ponticelli, S. K., Sutton, M., and Berdis, A. (2010) Selective Inhibition of DNA Replicase Assembly by a Non-natural Nucleotide: Exploiting the Structural Diversity of ATP-Binding Sites. ACS Chem Biol. 5, DOI: 10.1021/cb900218c.
19. Zhang, X., Lee, L., and Berdis, A. J. (2004) Evaluating the contributions of desolvation and base-stacking during translesion DNA synthesis. Org. Biomol. Chem. 2, 1703-1711.
20. Zhang, X., Lee, I., and Berdis, A. J. (2005) A potential chemotherapeutic strategy for the selective inhibition of promutagenic DNA synthesis by nonnatural, nucleotides. Biochemistry 44, 13111-13121. (Pubitemid 41377291)
21. Zhang, X., Lee, L., and Berdis, A. J. (2005) The use of nonnatural nucleotides to probe the contributions of shape complementarity and π-electron surface area during DNA polymerization. Biochemistry 44, 13101-13110. (Pubitemid 41377290)
22. Zhang, X., Lee, I., Zhou, X., and Berdis, A. J. (2006) Hydrophobicity, shape, and π-electron contributions during translesion DNA synthesis, J. Am. Chem. Soc. 128, 143-149. (Pubitemid 43100865)
23. Reineks, E. Z., and Berdis, A. J. (2004) Evaluating the contribution of base stacking during translesion DNA replication. Biochemistrv 43, 393-1104
24. Polli, J. W., Wring, S. A., Humphreys, J. E., Huang, L., Morgan, J. B., Webster, L. O., and Serabjit-Singh, C. S. (2001) Rational use of in vitro P-glycoprotein assays in drug discovery. J. Pharmacol. Exp. Ther. 299, 620-628. (Pubitemid 32979675)
25. King, K. M., Damaraju, V. L., Vickers, M. F., Yao, S. Y., Lang, T., Tackaberry, T. E., Mowles D. A., Ng, A. M., Young, J. D., and Cass, C. E. (2006) A comparison of the transportability, and its role in cytotoxicity, of clofarabine, cladribine, and fludarabine by recombinant human nucleoside transporters produced in three model expression systems. Mol. Pharmacol. 69, 346-353. (Pubitemid 43048921)
26. Garrigues, A., Loiseau, N., Delaforge, M., Ferte, J., Garrigos, M., Andre, F., and Orlowski, S. (2002) Characterization of two pharmacophores on the multidrug transporter P-glycoprotein. Mol Pharmacol 62, 1288-1298. (Pubitemid 35403824)
27. Copeland, R. A. (2005) Evaluation of enzyme inhibitors in drug discovery: A guide for medicinal chemists and pharmacologists, Wiley-Interscience, Hoboken, NJ.
28. Shapiro, A. B., and Ling, V. (1997) Positively cooperative sites for drug transport by P-glycoprotein with distinct drug specificities. Eur. J. Biochem. 250, 130-137.
29. Sterz, K., Mollmann, L., Jacobs, A., Baumert, D., and Wiese, M. (2009) Activators of P-glycoprotein: Structure-Activity Relationships and Investigation of their Mode of Action. ChemMedChem 4, 1897-1911.
30. Kondratov, R. V., Komarov, P. G., Becker, Y., Ewenson, A., and Gudkov, A. V. (2001) Small molecules that dramatically alter multidrug resistance phenotype by modulating the substrate specificity of P-glycoprotein.Proc. Natl. Acad. Sci. U.S.A. 98, 14078-14083. (Pubitemid 33116027)
31. Lagas, J. S., van Waterschoot, R. A., van Tilburg, V. A., Hillebrand, M. J., Lankheet, N., Rosing, H., Beijnen, J. H., and Schinkel, A. H. (2009) Brain accumulation of dasatinib is restricted by P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2) and can. be enhanced by elacridar treatment. Clin. Cancer Res. 15, 2344-2351.
32. Hugnet, C., Lespine, A., and Alvinerie, M. (2007) Multiple oral dosing of ketoconazole increases dog exposure to ivermectin. J.Pharm. Pharm. Sci. 10, 311-318. (Pubitemid 350055593)
33. Bartley, D. J., McAllister, H., Bartley, Y., Dupuy, J., Menez, C., Alvinerie, M., Jackson, F., and Lespine, A. (2009) P-Glycoprotein interfering agents potentiate ivermectin susceptibility in ivermectin sensitive and resistant isolates of Teladorsagia eircumcincta and Haemonchus contortus. 136, 1081-1088.