Inhibition of nucleoside transport and synergistic potentiation of methotrexate cytotoxicity by cimicifugoside, a triterpenoid from Cimicifuga simplex

European Journal of Pharmaceutical Sciences

Volumn 38, Issue 4, 2009, Pages 355-361

  Yawata, Ayako ^a   Matsuhashi, Yuko ^a   Kato, Hanako ^a   Uemura, Keiko ^a   Kusano, Genjiro ^b   Ito, Junko ^a   Chikuma, Toshiyuki ^a   Hojo, Hiroshi ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

Cimicifugoside; Cytotoxicity; Inhibitor; Methotrexate; Nucleoside transport

Indexed keywords

ADENOSINE; BUGBANOSIDE A; BUGBANOSIDE B; CIMICIFUGENIN; CIMICIFUGENIN A; CIMICIFUGOSIDE; DIPYRIDAMOLE; METHOTREXATE; NITROBENZYLTHIOINOSINE; O METHYLCIMICIFUGENIN; TERPENOID; THYMIDINE; TRITERPENOID; UNCLASSIFIED DRUG; URIDINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CANCER CELL CULTURE; CIMICIFUGA; CONTROLLED STUDY; CYTOTOXICITY; DRUG MECHANISM; DRUG POTENTIATION; HUMAN; HUMAN CELL; IC 50; NUCLEOSIDE TRANSPORT; PRIORITY JOURNAL;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CELLS, CULTURED; CIMICIFUGA; DRUG SYNERGISM; HUMANS; K562 CELLS; LANOSTEROL; METHOTREXATE; NUCLEOSIDES; PROTEIN TRANSPORT; TRITERPENES; U937 CELLS;

EID: 70349840426     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2009.08.011     Document Type: Article

References (41)

1. Aronow B., Toll D., Patrick J., McCartan K., and Ullman B. Dipyridamole-insensitive nucleoside transport in mutant murine T lymphoma cells. J. Biol. Chem. 261 (1986) 14467-14473
2. Baldwin S.A., Mackey J.R., Cass C.E., and Young J.D. Nucleoside transporters: molecular biology and implications for therapeutic development. Mol. Med. Today 5 (1999) 216-224
3. Belt J.A., and Noel L.D. Nucleoside transport in Walker 256 rat carcinosarcoma and S49 mouse lymphoma cells. Biochem. J. 232 (1985) 681-688
4. Boleti H., Coe I.R., Baldwin S.A., Young J.D., and Cass C.E. Molecular identification of the equilibrative NBMPR-sensitive (es) nucleoside transporter and demonstration of an equilibrative NBMPR-insensitive (ei) transport activity in human erythroleukemia (K562) cells. Neuropharmacology 36 (1997) 1167-1179
5. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the protein-dye binding. Anal. Biochem. 72 (1976) 248-254
6. Cabrita M.A., Baldwin S.A., Young J.D., and Cass C.E. Molecular biology and regulation of nucleoside and nucleobase transporter proteins in eukaryotes and prokaryotes. Biochem. Cell Biol. 80 (2002) 623-638
7. Carrier E.J., Auchampach J.A., and Hillard C.J. Inhibition of an equilibrative nucleoside transporter by cannabidiol: a mechanism of cannabinoid immunosuppression. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 7895-7900
8. Cass C.E., Young J.D., and Baldwin S.A. Recent advances in the molecular biology of nucleoside transporters of mammalian cells. Biochem. Cell Biol. 76 (1998) 761-770
9. Clumeck N. Current use of anti-HIV drugs in AIDS. J. Antimicrob. Chemother. 32 (1993) 133-138
10. Croxford J.L., and Yamamura T. Cannabinoids and the immune system: potential for the treatment of inflammatory diseases?. J. Neuroimmunol. 166 (2005) 3-18
11. Grem J.L., and Fischer P.H. Augmentation of 5-fluorouracil cytotoxicity in human colon cancer cells by dipyridamole. Cancer Res. 45 (1985) 2967-2972
12. Griffith D.A., and Jarvis S.M. Nucleoside and nucleobase transport systems of mammalian cells. Biochim. Biophys. Acta 1286 (1996) 153-181
13. Hammond J.R., and Archer R.G. Interaction of the novel adenosine uptake inhibitor 3-[1-(6,7-diethoxy-2-morpholinoquinazolin-4-yl)piperidine-4-yl]-1,6-dimethyl-2,4 (1H,3H)-quinazolinedione hydrochloride (KF24345) with the es and ei subtypes of equilibrative nucleoside transporters. J. Pharmacol. Exp. Ther. 308 (2004) 1083-1093
14. Hansen M.B., Nielsen S.E., and Berg K. Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J. Immunol. Methods 119 (1989) 203-210
15. Hemmi H., Kitame F., Ishida N., Kusano G., Kondo Y., and Nozoe S. Inhibition of thymidine transport into phytohemagglutinin-stimulated lymphocytes by triterpenoids from Cimicifuga species. J. Pharm. Dyn. 2 (1979) 339-349
16. Hemmi H., Kusano G., and Ishida N. Selective inhibition of nucleoside transport into mouse lymphoma L-5178Y cells by cimicifugoside. J. Pharm. Dyn. 3 (1980) 636-642
17. Howell S.B., Hom D., Sanga R., Vick J.S., and Abramson I.S. Comparison of the synergistic potentiation of etoposide, doxorubicin, and vinblastine cytotoxicity by dipyridamole. Cancer Res. 49 (1989) 3178-3183
18. Huang M., Wang Y., Cogut S.B., Mitchell B.S., and Graves L.M. Inhibition of nucleoside transport by protein kinase inhibitors. J. Pharmacol. Exp. Ther. 304 (2003) 753-760
19. Huang M., Wang Y., Collins M., Gu J.J., Mitchell B.S., and Graves L.M. Inhibition of nucleoside transport by p38 MAPK inhibitors. J. Biol. Chem. 277 (2002) 28364-28367
20. Jarvis S.M. Nitrobenzylthioinosine-sensitive nucleoside transport system: mechanism of inhibition by dipyridamole. Mol. Pharmacol. 30 (1986) 659-665
21. Jekunen A., Vick J., Sanga R., Chan T.C., and Howell S.B. Synergism between dipyridamole and cisplatin in human ovarian carcinoma cells in vitro. Cancer Res. 52 (1992) 3566-3571
22. Kusano A., Takahira M., Shibano M., Miyase T., and Kusano G. Studies on the constituents of Cimicifuga species XXI. Two new cyclolanostanol xylosides, bugbanosides A and B from Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 46 (1998) 1001-1007
23. Kusano G., Hojo S., Kondo Y., and Takemoto T. Studies on the constituents of Cimicifuga spp. XIII: Structure of cimicifugoside. Chem. Pharm. Bull. 25 (1977) 3182-3189
24. Kusano G. Studies on the constituents of Cimicifuga species (Japanese). Yakugaku Zasshi 121 (2001) 497-521
25. Malfait A.M., Gallily R., Sumariwalla P.F., Malik A.S., Andreakos E., Mechoulam R., and Feldmann M. Determinants of sensitivity and resistance to gemcitabine: the roles of human equilibrative nucleoside transporter 1 and deoxycytidine kinase in non-small cell lung cancer. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 9561-9566
26. Martin D., and Meckling-Gill K.A. Omega-3 polyunsaturated fatty acids increase purine but not pyrimidine transport in L1210 leukaemia cells. Biochem. J. 315 (1996) 329-333
27. Marz R., Wohlhueter R.M., and Plagemann P.G. Growth rate of cultured Novikoff rat hepatoma cells as a function of the rate of thymidine and hypoxanthine transport. J. Membr. Biol. 34 (1977) 277-288
28. McIvor R.S., Wohlhueter R.M., and Plagemann P.P. Uridine phosphorylase from Novikoff rat hepatoma cells: purification, kinetic properties, and its role in uracil anabolism. J. Cell. Physiol. 122 (1985) 397-404
29. Noji T., Takayama M., Mizutani M., Okamura Y., Takai H., Karasawa A., and Kusaka H. KF24345, an adenosine uptake inhibitor, suppresses lipopolysaccharide-induced tumor necrosis factor-α production and leucopenia via endogenous adenosine in mice. J. Pharmacol. Exp. Ther. 300 (2002) 200-205
30. Pastor-Anglada M., Casado F.J., Valdes R., Mata J., Garcia-Manteiga J., and Molina M. Complex regulation of nucleoside transporter expression in epithelial and immune system cells. Mol. Membr. Biol. 18 (2001) 81-85
31. Pastor-Anglada M., Felipe A., and Casado F.J. Transport and mode of action of nucleoside derivatives used in chemical and antiviral therapies. Trends Pharmacol. Sci. 19 (1998) 424-430
32. Paterson A.R.P., Lau E.Y., Dahlig E., and Cass C.E. A common basis for inhibition of nucleoside transport by dipyridamole and nitrobenzylthyoinosine?. Mol. Pharmacol. 18 (1980) 40-41
33. Roos H., and Pfleger K. Kinetics of adenosine uptake by erythrocytes, and the influence of dipyridamole. Mol. Pharmacol. 4 (1972) 417-425
34. SenGupta D.J., Lum P.Y., Lai Y., Schubochkina E., Bakken A.H., Schneider G., and Unadkat J.D. A single glycine mutation in the equilibrative nucleoside transporter gene, hENT1, alters nucleoside transport activity and sensitivity to nitrobenzylthioinosine. Biochemistry 41 (2002) 1512-1519
35. SenGupta D.J., and Unadkat J.D. Glycine 154 of the equilibrative nucleoside transporter, hENT1, is important for nucleoside transport and for conferring sensitivity to the inhibitors nitrobenzylthioinosine, dipyridamole, and dilazep. Biochem. Pharmacol. 67 (2004) 453-458
36. Spratlin J., Sangha R., Glubrecht D., Dabbagh L., Young J.D., Dumontet C., Cass C., Lai R., and Mackey J.R. The absence of human equilibrative nucleoside transporter 1 is associated with reduced survival in patients with gemcitabine-treated pancreas adenocarcinoma. Clin. Cancer Res. 10 (2004) 6956-6961
37. Stoeckler J.D., Rosenfield C.G., Chu S.H., Li S.Y., Acton E.M., Ryan K.J., and Parks Jr. R.E. Inhibition of nucleoside transport by nitrobenzylthioformycin analogs. Biochem. Pharmacol. 40 (1990) 615-619
38. Sundaram M., Yao S.Y., Ng A.M.L., Griffiths M., Cass C.E., Baldwin S.A., and Young J.D. Chimeric constructs between human and rat equilibrative nucleoside transporters (hENT1 and rENT1) reveal hENT1 structural domains interacting with coronary vasoactive drugs. J. Biol. Chem. 273 (1998) 21519-21525
39. Ward J.L., Sherali A., Mo Z.P., and Tse C.M. Kinetic and pharmacological properties of cloned human equilibrative nucleoside transporters, ENT1 and ENT2, stably expressed in nucleoside transporter-deficient PK15 cells. J. Biol. Chem. 275 (2000) 8375-8381
40. Ward J.L., and Tse C.M. Nucleoside transport in human colonic epithelial cell lines: evidence for two Na+-independent transport systems in T84 and Caco-2 cells. Biochim. Biophys. Acta 1419 (1999) 15-22
41. Weber G. Biochemical strategy of cancer cells and the design of chemotherapy: G. H. A. Clowes memorial lecture. Cancer Res. 43 (1983) 3466-3492