Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 8, 2008, Pages 4626-4651

  Jain, Hiteshkumar D ^a   Zhang, Chunchun ^a   Zhou, Shuo ^a   Zhou, Hao ^a   Ma, Jun ^a   Liu, Xiaoxiang ^a   Liao, Xuebin ^a   Deveau, Amy M ^a   Dieckhaus, Christine M ^b   Johnson, Michael A ^b   Smith, Kirsten S ^b   Macdonald, Timothy L ^b   Kakeya, Hideaki ^c   Osada, Hiroyuki ^c   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

^c Japan Science and Technology Agency   (Japan)

Author keywords

Anticancer; Antimitotic; Breast cancer resistance protein; Tryprostatin A

Indexed keywords

BREAST CANCER RESISTANCE PROTEIN; DNA TOPOISOMERASE (ATP HYDROLYSING); PROTEIN INHIBITOR; TRYPROSTATIN A; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CELL STRAIN MCF 7; CONTROLLED STUDY; CYTOTOXICITY; DRUG INHIBITION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MICROTUBULE ASSEMBLY; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL PROLIFERATION; DNA TOPOISOMERASES, TYPE II; DRUG RESISTANCE, NEOPLASM; ENZYME INHIBITORS; HUMANS; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; PIPERAZINES; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN;

EID: 42149164521     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.02.050     Document Type: Article

References (61)

1. Nasmyth K. Science 274 (1996) 1643
2. Paulovich A.G., Toczyski D.P., and Hartwell L.H. Cell 88 (1997) 315
3. Pardee A.B. PNAS 71 (1974) 1286
4. Osada H., Cui C.-B., Onose R., and Hanaoka F. Bioorg. Med. Chem. 5 (1997) 193
5. Osada H. J. Antibiotics 51 (1998) 973
6. Cui C.-B., Kakeya H., Okada G., Onose R., Ubukata M., Takahashi I., Isono K., and Osada H. J. Antibiotics 48 (1995) 1382
7. Cui C.-B., Kakeya H., and Osada H. J. Antibiotics 49 (1996) 534
8. Cui C.-B., Kakeya H., Okada G., Onose R., and Osada H. J. Antibiotics 49 (1996) 527
9. Gan T., and Cook J.M. Tetrahedron Lett. 38 (1997) 1301
10. Ma C., Liu X., Li X., Flippen-Anderson J., Yu S., and Cook J.M. J. Org. Chem. 66 (2001) 4525
11. Zhao S., Gan T., Yu P., and Cook J.M. Tetrahedron Lett. 39 (1998) 7009
12. Zhao S., Smith K.S., Deveau A.M., Dieckhaus C.M., Johnson M.A., Macdonald T.L., and Cook J.M. J. Med. Chem. 45 (2002) 1559
13. Usui T., Kondoh M., Cui C.-B., Mayumi T., and Osada H. Biochem. J. 333 (1998) 543
14. Amos L.A. Curr. Opin. Struct. Biol. 10 (2000) 236
15. Maiato H., Sampaio P., and Sunkel C.E. Int. Rev. Cytol. 241 (2005) 53
16. Hamel E., Campo A.A.d., Lowe M.C., Waxman P.G., and Lin C.M. Biochemistry 21 (1982) 503
17. Zhou J., and Giannakakou P. Anti-Cancer Agents Med. Chem. 5 (2005) 65
18. Shi Q., Chen K., Morris-Natschke S.L., and Lee K.-H. Curr. Pharm. Des. 4 (1998) 219
19. Mani S., Macapinlac M., Goel S., Verdier-Pinard D., Fojo T., Rothenberg M., and Colevas D. Anti-Cancer Drugs 15 (2004) 553
20. Beckers T., and Mahboobi S. Drugs Future 28 (2003) 767
21. Rowinsky, E.; Donehower, R. C. In Cancer Principles and Practice of Oncology; DeVita, V. T., Hellman, S., Rosenburg, S. A., Eds.; Lippincott-Raven: Philadelphia, 2001; pp. 431-452.
22. Pettit G.R., Singh S.B., Hamel E., Lin C.M., Alberts D.S., and Garcia-Kendall D. Experientia 45 (1989) 209
23. Blokhin A.V., Yoo H.-D., Geralds R.S., Nagle D.G., Gerwick W.H., and Hamel E. Mol. Pharmacol. 48 (1995) 523
24. Damayanthi Y., and Lown J.W. Curr. Med. Chem. 5 (1998) 205
25. Flörsheimer A., and Altmann K.-H. Expert Opin. Ther. Patents 11 (2001) 951
26. Poncet J. Curr. Pharm. Des. 5 (1999) 139
27. Simpson D., and Wagstaff A.J. Am. J. Cancer 2 (2003) 373
28. Mazumdar M., Parrack P.K., Mukhopadhyay K., and Bhattacharyya B. Biochemistry 31 (1992) 6470
29. Lage H., and Dietel M. Lancet Oncol. 1 (2000) 169
30. Doyle L.A., Yang W., Abruzzo L.V., Krogmann T., Gao Y., Rishi A.K., and Ross D.D. PNAS 95 (1998) 15665
31. Abbott B.L. Hematol. Oncol. 21 (2003) 115
32. Allen J.D., and Schinkel A.H. Mol. Cancer Ther. 1 (2002) 427
33. Doyle L.A., and Ross D.D. Oncogene 22 (2003) 7340
34. Benderra Z., Faussat A.-M., Sayada L., Perrot J.-Y., Chaoui D., Marie J.-P., and Legrand O. Clin. Cancer Res. 10 (2004) 7896
35. Uggla B., Stahl E., Wagsaeter D., Paul C., Karlsson M.G., Sirsjoe A., and Tidefelt U. Leukemia Res. 29 (2005) 141
36. Candeil L., Gourdier I., Peyron D., Vezzio N., Copois V., Bibeau F., Orsetti B., Scheffer G.L., Ychou M., Khan Q.A., Pommier Y., Pau B., Martineau P., and Del Rio M. Int. J. Cancer 109 (2004) 848
37. Ross D.D. Leukemia 14 (2000) 467
38. Sauerbrey A., Sell W., Steinbach D., Voigt A., and Zintl F. Br. J. Haematol. 118 (2002) 147
39. Ross D.D., Yang W., Abruzzo L.V., Dalton W.S., Schneider E., Lage H., Dietel M., Greenberger L., Cole S.P., and Doyle L.A. J. Natl. Cancer Inst. 91 (1999) 429
40. Robey R.W., Medina-Perez W.Y., Nishiyama K., Lahusen T., Miyake K., Litman T., Senderowicz A.M., Ross D.D., and Bates S.E. Clin. Cancer Res. 7 (2001) 145
41. Houghton P.J., Germain G.S., Harwood F.C., Schuetz J.D., Stewart C.F., Buchdunger E., and Traxler P. Cancer Res. 64 (2004) 2333
42. Rabindran S.K., Ross D.D., Doyle L.A., Yang W., and Greenberger L.M. Cancer Res. 60 (2000) 47
43. Woehlecke H., Osada H., Herrmann A., and Lage H. Int. J. Cancer 107 (2003) 721
44. Maliepaard M., van Gastelen M.A., Tohgo A., Hausheer F.H., van Waardenburg R.C.A.M., de Jong L.A., Pluim D., Beijnen J.H., and Schellens J.H.M. Clin. Cancer Res. 7 (2001) 935
45. Larock R.C., Yum E.K., and Refvik M.D. J. Org. Chem. 63 (1998) 7652
46. Larock R.C., and Yum E.K. J. Am. Chem. Soc. 113 (1991) 6689
47. Feldman K.S., Eastman K.J., and Lessene G. Org. Lett. 4 (2002) 3525
48. Dieck H.A., and Heck F.R. J. Organomet. Chem. 93 (1975) 259
49. Lifer, S. Master thesis, University of Wisconsin-Milwaukee, Milwaukee, WI, 1987.
50. Nyffeler P.T., Liang C.-H., Koeller K.M., and Wong C.-H. J. Am. Chem. Soc. 124 (2002) 10773
51. Liu Q., and Tor Y. Org. Lett. 5 (2003) 2571
52. Spitzner J.R., and Muller M.T. Nucleic Acids Res. 16 (1988) 5533
53. Muller M.T., Spitzner J.R., DiDonato J.A., Mehta V.B., Tsutsui K., and Tsutsui K. Biochemistry 27 (1988) 8369
54. Kondoh M., Usui T., Mayumi T., and Osada H. J. Antibiotics 51 (1998) 801
55. Depew K.M., Danishefsky S.J., Rosen N., and Sepp-Lorenzino L. J. Am. Chem. Soc. 118 (1996) 12463
56. We thank the Developmental Therapeutics Program of the National Cancer Institute for performing the in vitro anticancer evaluation.
57. Turner J.G., Gump J.L., Zhang C., Cook J.M., Marchion D., Hazlehurst L., Munster P., Schell M.J., Dalton W.S., and Sullivan D.M. Blood 108 (2006) 3881
58. Kakeya H., Onose R., Liu P.C., Onozawa C., Matsumura F., and Osada H. Cancer Res. 58 (1998) 704
59. Bulman, A. L. Kinases and Drugs Targeting the microtubule System. Ph.D. Thesis, University of Virginia, Charlottesville, VA, 1998.
60. Barltrop J.A., Owen T.C., Cory A.H., and Cory J.G. Bioorg. Med. Chem. Lett. 1 (1991) 611
61. Cory A.H., Owen T.C., Barltrop J.A., and Cory J.G. Cancer Commun. 3 (1991) 207