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Chemical Compound Review

AG-L-65518     (1R,5S,6S,7R,10S,14S,16S)- 6,10-dihydroxy-1...

Synonyms: AC1L8WWS, CTK8F9473, NCI60_030305
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Disease relevance of Epothilone B


Psychiatry related information on Epothilone B


High impact information on Epothilone B


Chemical compound and disease context of Epothilone B


Biological context of Epothilone B


Anatomical context of Epothilone B


Associations of Epothilone B with other chemical compounds


Gene context of Epothilone B

  • These results indicate that in low-level epothilone B- or Taxol-resistant A549 cells, increased caveolin-1 expression occurs independently of P-glycoprotein expression [25].
  • Two drug-resistant A549 cell lines (one 9-fold resistant to Taxol and the other 1.5-fold resistant to epothilone B), both of which express no P-glycoprotein, demonstrate a significant increase in the expression of caveolin-1 [25].
  • On the other hand, epothilone B prevented microtubule disruption and inhibited OxLDL-dependent increases in arginase activity and attenuated OxLDL-dependent decreases in NOx [26].
  • METHODS: Fresh human tumor or normal tissue disks (2 x 1 mm) from fresh surgical specimens were incorporated into fibrin-thrombin clots overlain with nutrient medium containing either 20% fetal bovine serum alone or in combination with Epothilone B, a tubulin inhibitor with antiangiogenic properties [27].
  • Treatment of tumors or normal tissues with Epothilone B at doses less than 10-8 mol/L was ineffective [27].

Analytical, diagnostic and therapeutic context of Epothilone B


  1. Patupilone (epothilone B) inhibits growth and survival of multiple myeloma cells in vitro and in vivo. Lin, B., Catley, L., LeBlanc, R., Mitsiades, C., Burger, R., Tai, Y.T., Podar, K., Wartmann, M., Chauhan, D., Griffin, J.D., Anderson, K.C. Blood (2005) [Pubmed]
  2. Epothilone B analogue (BMS-247550)-mediated cytotoxicity through induction of Bax conformational change in human breast cancer cells. Yamaguchi, H., Paranawithana, S.R., Lee, M.W., Huang, Z., Bhalla, K.N., Wang, H.G. Cancer Res. (2002) [Pubmed]
  3. Both microtubule-stabilizing and microtubule-destabilizing drugs inhibit hypoxia-inducible factor-1alpha accumulation and activity by disrupting microtubule function. Escuin, D., Kline, E.R., Giannakakou, P. Cancer Res. (2005) [Pubmed]
  4. Ixabepilone (epothilone B analogue BMS-247550) is active in chemotherapy-naive patients with hormone-refractory prostate cancer: a Southwest Oncology Group trial S0111. Hussain, M., Tangen, C.M., Lara, P.N., Vaishampayan, U.N., Petrylak, D.P., Colevas, A.D., Sakr, W.A., Crawford, E.D. J. Clin. Oncol. (2005) [Pubmed]
  5. Cathepsin B mediates caspase-independent cell death induced by microtubule stabilizing agents in non-small cell lung cancer cells. Bröker, L.E., Huisman, C., Span, S.W., Rodriguez, J.A., Kruyt, F.A., Giaccone, G. Cancer Res. (2004) [Pubmed]
  6. A highly epothilone B-resistant A549 cell line with mutations in tubulin that confer drug dependence. Yang, C.P., Verdier-Pinard, P., Wang, F., Lippaine-Horvath, E., He, L., Li, D., Höfle, G., Ojima, I., Orr, G.A., Horwitz, S.B. Mol. Cancer Ther. (2005) [Pubmed]
  7. Evaluation of epothilone B analog in advanced soft tissue sarcoma: a phase II study of the phase II consortium. Okuno, S., Maples, W.J., Mahoney, M.R., Fitch, T., Stewart, J., Fracasso, P.M., Kraut, M., Ettinger, D.S., Dawkins, F., Erlichman, C. J. Clin. Oncol. (2005) [Pubmed]
  8. Flavopiridol down-regulates antiapoptotic proteins and sensitizes human breast cancer cells to epothilone B-induced apoptosis. Wittmann, S., Bali, P., Donapaty, S., Nimmanapalli, R., Guo, F., Yamaguchi, H., Huang, M., Jove, R., Wang, H.G., Bhalla, K. Cancer Res. (2003) [Pubmed]
  9. Gene expression and mitotic exit induced by microtubule-stabilizing drugs. Chen, J.G., Yang, C.P., Cammer, M., Horwitz, S.B. Cancer Res. (2003) [Pubmed]
  10. Phase II trial of ixabepilone, an epothilone B analog, given daily for three days every three weeks, in metastatic breast cancer. Denduluri, N., Lee, J.J., Walshe, J., Berman, A.W., Vatas, U., Chow, C.K., Steinberg, S.M., Cox, M.C., Low, J.A., Swain, S.M. Investigational new drugs (2007) [Pubmed]
  11. Isolation and characterization of the epothilone biosynthetic gene cluster from Sorangium cellulosum. Julien, B., Shah, S., Ziermann, R., Goldman, R., Katz, L., Khosla, C. Gene (2000) [Pubmed]
  12. Phase I study of temozolomide plus paclitaxel in patients with advanced malignant melanoma and associated in vitro investigations. Azzabi, A., Hughes, A.N., Calvert, P.M., Plummer, E.R., Todd, R., Griffin, M.J., Lind, M.J., Maraveyas, A., Kelly, C., Fishwick, K., Calvert, A.H., Boddy, A.V. Br. J. Cancer (2005) [Pubmed]
  13. Tumor necrosis factor-alpha related gene response to Epothilone B in ovarian cancer. Khabele, D., Lopez-Jones, M., Yang, W., Arango, D., Gross, S.J., Augenlicht, L.H., Goldberg, G.L. Gynecol. Oncol. (2004) [Pubmed]
  14. Late activation of apoptotic pathways plays a negligible role in mediating the cytotoxic effects of discodermolide and epothilone B in non-small cell lung cancer cells. Bröker, L.E., Huisman, C., Ferreira, C.G., Rodriguez, J.A., Kruyt, F.A., Giaccone, G. Cancer Res. (2002) [Pubmed]
  15. Differential mitotic responses to microtubule-stabilizing and -destabilizing drugs. Chen, J.G., Horwitz, S.B. Cancer Res. (2002) [Pubmed]
  16. Epothilone B stabilizes microtubuli of macrophages like taxol without showing taxol-like endotoxin activity. Muhlradt, P.F., Sasse, F. Cancer Res. (1997) [Pubmed]
  17. The 12,13-diol cyclization approach for a truly stereocontrolled total synthesis of epothilone B and the synthesis of a conformationally restrained analogue. Martin, H.J., Pojarliev, P., Kählig, H., Mulzer, J. Chemistry (Weinheim an der Bergstrasse, Germany) (2001) [Pubmed]
  18. Improved synthesis of epothilone B employing alkylation of an alkyne for assembly of subunits. White, J.D., Sundermann, K.F., Carter, R.G. Org. Lett. (1999) [Pubmed]
  19. Suppression of microtubule dynamics by epothilone B is associated with mitotic arrest. Kamath, K., Jordan, M.A. Cancer Res. (2003) [Pubmed]
  20. Regulation of Bax activation and apoptotic response to microtubule-damaging agents by p53 transcription-dependent and -independent pathways. Yamaguchi, H., Chen, J., Bhalla, K., Wang, H.G. J. Biol. Chem. (2004) [Pubmed]
  21. A Phase II trial of epothilone B analogue BMS-247550 (NSC #710428) ixabepilone, in patients with advanced pancreas cancer: a Southwest Oncology Group study. Whitehead, R.P., McCoy, S., Rivkin, S.E., Gross, H.M., Conrad, M.E., Doolittle, G.C., Wolff, R.A., Goodwin, J.W., Dakhil, S.R., Abbruzzese, J.L. Investigational new drugs. (2006) [Pubmed]
  22. Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D. White, J.D., Carter, R.G., Sundermann, K.F., Wartmann, M. J. Am. Chem. Soc. (2001) [Pubmed]
  23. In vivo evaluation of ixabepilone (BMS247550), a novel epothilone B derivative, against pediatric cancer models. Peterson, J.K., Tucker, C., Favours, E., Cheshire, P.J., Creech, J., Billups, C.A., Smykla, R., Lee, F.Y., Houghton, P.J. Clin. Cancer Res. (2005) [Pubmed]
  24. Derivatization of the C12-C13 functional groups of epothilones A, B and C. Sefkow, M., Kiffe, M., Höfle, G. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
  25. Upregulation of caveolin-1 and caveolae organelles in Taxol-resistant A549 cells. Yang, C.P., Galbiati, F., Volonte, D., Horwitz, S.B., Lisanti, M.P. FEBS Lett. (1998) [Pubmed]
  26. Oxidized low-density lipoprotein-dependent endothelial arginase II activation contributes to impaired nitric oxide signaling. Ryoo, S., Lemmon, C.A., Soucy, K.G., Gupta, G., White, A.R., Nyhan, D., Shoukas, A., Romer, L.H., Berkowitz, D.E. Circ. Res. (2006) [Pubmed]
  27. Development of a novel in vitro human tissue-based angiogenesis assay to evaluate the effect of antiangiogenic drugs. Woltering, E.A., Lewis, J.M., Maxwell, P.J., Frey, D.J., Wang, Y.Z., Rothermel, J., Anthony, C.T., Balster, D.A., O'Leary, J.P., Harrison, L.H. Ann. Surg. (2003) [Pubmed]
  28. Activities of the microtubule-stabilizing agents epothilones A and B with purified tubulin and in cells resistant to paclitaxel (Taxol(R)). Kowalski, R.J., Giannakakou, P., Hamel, E. J. Biol. Chem. (1997) [Pubmed]
  29. Epothilones: a novel class of non-taxane microtubule-stabilizing agents. Altaha, R., Fojo, T., Reed, E., Abraham, J. Curr. Pharm. Des. (2002) [Pubmed]
  30. Pilot study of epothilone B analog (BMS-247550) and estramustine phosphate in patients with progressive metastatic prostate cancer following castration. Smaletz, O., Galsky, M., Scher, H.I., DeLaCruz, A., Slovin, S.F., Morris, M.J., Solit, D.B., Davar, U., Schwartz, L., Kelly, W.K. Ann. Oncol. (2003) [Pubmed]
  31. Preclinical pharmacokinetics and oral bioavailability of BMS-310705, a novel epothilone B analog. Kamath, A.V., Chang, M., Lee, F.Y., Zhang, Y., Marathe, P.H. Cancer Chemother. Pharmacol. (2005) [Pubmed]
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