Epothilones: novel microtubule-stabilising agents

Bibliography

• SCHIFF PB, FANT J, HORWITZ SB: Promotion of micro-tubule assembly in vitro by taxol. Nature (1979) 277:665–667.
   PubMed Web of Science ®Google Scholar
• ROWINSKY EK: The development and clinical utility of the taxane class of antimicrotubule chemotherapy agents. Ann. Rev. Med. (1997) 48:353-374. A recent review of preclinical and clinical attributes of paclitaxel and docetaxel.
   Google Scholar
• Microtubulas Hyams JS, Lloyd CVV (Eds.), Wiley-Liss, Inc.,New York (1994).
   Google Scholar
• JORDAN MA, TOSO RJ, THROWER D, WILSON L: Mechanism of mitotic block and inhibition of cell prolifera-tion by taxol at low concentrations. Proc. Natl. Acad. Sci. USA (1993) 90:9552-9556. Demonstration that low concentrations of paclitaxel disrupt mitotic microtubules and lead to cytotoxicity without perturbing non-mitotic micr otubules.
   Google Scholar
• PANDA D, DAIJO JE, JORDAN MA, WILSON L: Kinetic stabilization of microtubule dynamics at steady state in vitro by substoichiometric concentrations of tubulin-colchicine complex. Biochem. (1995) 34:9921–9929.
   PubMed Web of Science ®Google Scholar
• DHAMADHARAN RI, JORDAN MA, THROWER D, WILSON L: Vinblastine suppress es dynamics of individual micro-tubules in living cells. Mol Biol. Cell (1995) 6:1215–1229.
   PubMed Web of Science ®Google Scholar
• JORDAN MA, VVENDELLK, GARDINER S eta': Mitotic block induced in hela cells by low concentrations of paclitaxel (taxol) results in abnormal mitotic exit and apoptotic cell death. Cancer Res. (1996) 56:816–825.
   PubMed Web of Science ®Google Scholar
• THOMPSON CB: Apoptosis in the pathcgenesis and treatment of disease. Science (1995) 267:1456–1462.
   PubMed Web of Science ®Google Scholar
• BHALLA K, IBRADO AM, TOURKINA E et aL Taxol induces internucleosomal DNA fragmentation associated with programmed cell death in human myeloid leukemia cells. Leukemia (1993) 7:563–568.
   PubMed Web of Science ®Google Scholar
• WOODS CM, ZHU J, MCQUENEY PA, BOLLAG DM, LAZ-
   Google Scholar
• •ARIDES E: Taxol-induced mitotic block triggers rapid onset of a p53-independent apoptotic pathway. Mol Med. (1995) 1:506-527. Characterisation of paclitaxel-mediated cell cycle arrest, suggesting a p53-independent apoptotic pathway.
   Google Scholar
• MILROSS CG, MASON KA, HUNTER NR eta]: Relationship of mitotic arrest and apoptosis to antitumor effect of paclitaxel. J. Nag. Cancer Inst. (1996) 88:1308–1314.
   PubMed Web of Science ®Google Scholar
• LOWE SW, RULEY HE, JACKS T, HOUSMAN DE: p53-de-pendent apoptosis modulates the cytotoxicity of anti-cancer agents. Cell (1993) 74:957–967.
   PubMed Web of Science ®Google Scholar
• LEVINE AJ: p53, the cellular gatekeeper for growth and division. Cell (1997) 88:323–331.
   PubMed Web of Science ®Google Scholar
• STROBEL T, SWANSON L, KORSMEYER S, CANNISTRA SA:BAX enhances paclitaxel-induced apoptosis through a p53-independent pathway. Proc. Nag Acad. Sci. USA (1996) 93:14094–14099.
   PubMed Web of Science ®Google Scholar
• WAHL AF, DONALDSON KL, FAIRCHILD C et al: Loss ofnormal p53 function confers sensitization to taxol by increasing G2/M arrest and apoptosis. Nature Med. (1996) 2:72–79.
   PubMed Web of Science ®Google Scholar
• LI WW, CORDON-CARDO C, CHEN Q, JHANWAR SC, BERTINO JR: Establishment, characterization and drug sensitivity of four new human soft tissue sarcoma cell lines. Int. J. Cancer (1996) 68:514–519.
   PubMed Web of Science ®Google Scholar
• SAFRAN H, KING T, CHOY H eta].: p53 mutations do not predict response to paclitaxel/radiation for non-small cell lung carcinoma. Cancer (1996) 78:1203–1210.
   Google Scholar
• HAMEL E: Antimitotic natural products and their inter-actions with tubulin. Med. Res. Rev. (1996) 2:207–231.
   Web of Science ®Google Scholar
• BOLLAG DM, MCQUENEY PA, ZHU J eta].: Epothilones, a new class of microtubtde -stabilizing agents with a taxol-like mechanism of action. Cancer Res. (1995) 55:2325-2333. First report of epothilone activity in stabilising microtubules, displac-ing paclitaxel binding and mitotic arrest leading to cell toxicity. First demonstration of epothilone activity against a P-glycoprotein over-expressing paclitaxel-resistant cell line.
   Google Scholar
• TER HAAR E, KOWALSKI RJ, HAMEL E et al.: Discodermolide, a cytotoxic marine agent that stabilizes micro-tubules more potently than taxol. Biochemistry (1996) 35:243-250. First thorough in vitro characterisation of discodermolide's micro-tubule stabilising properties.
   Google Scholar
• HUNG DT, CHEN J, SCHREIBER SL:-Discodermolide binds to microtubules in stoichiometric ratio to tubulindimers, blocks taxol binding and results in mitotic arrest. Chem. Biol. (1996) 3:287-293. Analysis of discodermolide effects on cell cycle arrest, tubulin binding and paclitaxel displacement.
   Google Scholar
• KOWALSKI RJ, GIANNAKAKOU P, HAMEL E: Activities of the microtubule-stabilizing agents epothilones A and Bwith purified tubulin and in cells resistant to paclitaxel (Taxol®). J. Biol. Chem. (1997) 272:2534-2541. Analysis of epothilone activity against purified tubulin and demon-stration of cytotoxicity against a paclitaxel-resistant cell line with an altered tubulin.
   Google Scholar
• HORWITZ SB, COHEN D, RAO S eta].: Taxol: mechanismsof action and resistance. Monogr. Nag. Cancer Inst. (1993) 15:55–61.
   Google Scholar
• JAFFREZOU JP, DUMONTET C, DERRY WM et al: Novelmechanism of resistance to paclitaxel (Taxol®) in hu-man K562 leukemia cells by combined selection with PSC 833. Oncol. Res. (1995) 7:517–527.
   PubMed Web of Science ®Google Scholar
• RANGANATHAN S, DEXTER DW, BENETATOS CA et al.: Increase of iii- and iva-tubulin isotypes in human pros-tate carcinoma cells as a result of estramustine resis-tance. Cancer Res. (1996) 56:2584–2589.
   PubMed Web of Science ®Google Scholar
• HUANG Y, IBRADO AM, REED JC eta].: Co-expression of several molecular mechanisms of multidrug-resistance and their significance for paclitaxel cytotoxicity in human AML HL-60 cells. Leukemia (1997) 11:253–257.
   Google Scholar
• YU D, LIU B, TAN M et al.: Overexpression of c-erbb-2/neu in breast cancer cells confers increased resis-tance to taxol via MDR-1-independent mechanisms. Oncogene (1996) 13:1359–1365.
   PubMed Web of Science ®Google Scholar
• HOEFLE G, BEDORF N, STEINMETZ H et al.: Epothilone A and B - novel 16-membered macrolides with cytotoxic activity: isolation, crystal structure, and conformation in solution. Angew. Chem. Irk Ed. Engl. (1996) 35:1567–1569.
   Web of Science ®Google Scholar
• WINKLER JD, AXELSEN PH: A model for the taxol (pacli-taxel) /epothilone pharmacophore. Bioorg Med. Chem. Leg. (1996) 6:2963–2966.
   Web of Science ®Google Scholar
• BALOG A, MENG D, KAMENECKA T eta].: Total synthesis of 0 -epothilone A. Angew. Chem. Int Ed. Engl. (1996) 35:2801–2803.
   Google Scholar
• YANG Z, HEY, VOURLOUMIS D, VALLBERG H, NICOLAOUKC: Total synthesis of epothilone A: the olefin metathe-sis approach. Angew. Chem. Int Ed. Engl. (1997) 36:166–168.
   Web of Science ®Google Scholar
• SCHINZER D, LIMBERG A, BAUER A, BOHM OM, CORDES M: Total synthesis of 0-epothilone A. Angew. Chem. Int Ed. Engl. (1997) 36:523–524.
   Web of Science ®Google Scholar
• NICOLAOU KC, WINSSINGER N, PASTOR J eta].: Synthesis of epothilone A and B in solid and solution phase. Nature (1997) 387:268–272.
   Google Scholar
• SU DS, MENG D, BERTINATO P eta].: Total synthesis of 0-epothilone B: an extension of the suzuki coupling method and insights into structure-activity relation-ships of the epothilones. Angew. Chem. Int Ed. Engl. (1997) 36:757–759.
   Google Scholar
• GUNASEKERA SP, GUNASEKERA M, LONGLEY RE, SCHULTE GK: Discodermolide, a new bioactive polyhy-droxylated lactone from the marine sponge, Discoder-mia dissoluta. Org Chem. (1990) 55:4912–4915.
   Web of Science ®Google Scholar
• NERENBERG JB, HUNG DT, SOMERS PK, SCHREIBER SL:Total synthesis ofthe immunosuppressive agent (-)-dis-codermolide../. Am. Chem. Soc. (1993) 115:12621–12622.
   Web of Science ®Google Scholar
• SPARREBOOM A, VAN ASPEREN J, MAYER U et al: Limited oral bioavailability and active epithelial excretion of paclitaxel (taxol) caused by P-glycoprotein in the intes - tine. Proc. Natl. Acad. Sci. USA (1997) 94:2031–2035.
   PubMed Web of Science ®Google Scholar
• BLAGOSKLONNY MV, SCHULTE TW, NGUYEN P et al.: Taxol induction of p21wAF1 and p53 requires crafl. Cancer Res. (1995) 55:4623–4626.
   PubMed Web of Science ®Google Scholar
• HALDAR S, CHINTAPALLI J, CROCE C: Taxol induces bc1-2 phosphorylation and death of prostate cancer cells. Cancer Res. (1996) 56:1253–1255.
   PubMed Web of Science ®Google Scholar
• HALDAR S, JENA N, CROCE C: Inactivation of bc1-2 by phosphorylation. Proc. Natl. Acad. Sci. USA (1995) 92:4507–4511.
   PubMed Web of Science ®Google Scholar
• HALDAR S, BASU A, CROCE CM: Bc12 is the guardian of microtubule integrity. Cancer Res. (1997) 57:229-233. Postulation of a Bc12-mediated pathway of apopt osis which is distinct from the apoptotic pathway induced by DNA damaging agents.
   Google Scholar
• MENG D, SU DS, BALOG A et al: Remote effects in macrolide formation through ring-forming olefin metathesis: an application to the synthesis of fully active epothilone congeners. I. Am. Chem. Soc. (1997) 119:2733-2734. First report of biochemical and biological activity of epothilone analogues.
   Google Scholar
• POUVELLE B, FARLEY PJ, LONG CA, TARASCHI T: Taxol arrests the development of blood-stage Plasmodium falciparum in vitro and Plasmodium chabaudi adami in malaria-infected mice. J. Clin. Invest (1994) 94:413–417.
   PubMed Web of Science ®Google Scholar
• WOO DO, MIAO SY, PELAYO JC, WOOLF AS: Taxol inhib-its progression of congenital polycystic kidney disease. Nature (1994) 368:750–753.
   PubMed Web of Science ®Google Scholar