A comparison of signaling activities induced by taxol and desoxyepothilone B

Journal of Chemotherapy

Volumn 16, Issue 6, 2004, Pages 563-576

  Bergstralh, D T ^a   Taxman, D J ^b   Chou, T C ^c   Danishefsky, S J ^c   Ting, Jenny P Y ^a,b  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

DEpoB; MDR; MEK; P gp; Taxol

Indexed keywords

1,4 DIAMINO 1,4 BIS(2 AMINOPHENYLTHIO) 2,3 DICYANOBUTADIENE; 12,13 DESOXYEPOTHILONE B; COLCHICINE; EPOTHILONE DERIVATIVE; GLYCOPROTEIN P; MITOGEN ACTIVATED PROTEIN KINASE; MITOGEN ACTIVATED PROTEIN KINASE INHIBITOR; NOCODAZOLE; OLOMOUCINE; PACLITAXEL; ROSCOVITINE; UNCLASSIFIED DRUG;

CELL DEATH; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG EFFICACY; DRUG MECHANISM; GENE EXPRESSION REGULATION; HUMAN; HUMAN CELL; INHIBITION KINETICS; MICROTUBULE ASSEMBLY; NUCLEOTIDE SEQUENCE; PROTEIN EXPRESSION; REVIEW; SENSITIVITY ANALYSIS; SIGNAL TRANSDUCTION; UNINDEXED SEQUENCE;

EID: 12544259215     PISSN: 1120009X     EISSN: None     Source Type: Journal    
DOI: 10.1179/joc.2004.16.6.563     Document Type: Review

References (55)

1. Schiff PB, Fant J, Horwitz SB Promotion of microtubule assembly in vitro by taxol. Nature 1979; 277(5698): 665-7.
2. Horwitz SB, Cohen D, Rao S, Ringel I, Shen HJ, Yang CP Taxol: Mechanisms of action and resistance. J Natl Cancer Inst Monogr 1993; 15): 55-61.
3. Sorger PK, Dobles M, Tournebize R, Hyman AA Coupling cell division and cell death to microtubule dynamics. Curr Opin Cell Biol 1997; 9(6): 807-14.
4. Bollag DM, McQueney PA, Zhu J, et al. Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action. Cancer Res 1995; 55(11): 2325-33.
5. Kowalski RJ, Giannakakou P, Hamel E Activities of the microtubule-stabilizing agents epothilones a and b with purified tubulin and in cells resistant to paclitaxel (taxol(r)). J Biol Chem 1997; 272(4): 2534-41.
6. Chou TC, Zhang XG, Balog A, et al. Desoxyepothilone b: An efficacious microtubule-targeted antitumor agent with a promising in vivo profile relative to epothilone b. Proc Natl Acad Sci U S A 1998; 95(16): 9642-7.
7. Chou TC, Zhang XG, Harris CR, et al. Desoxyepothilone b is curative against human tumor xenografts that are refractory to paclitaxel. Proc Natl Acad Sci U S A 1998; 95(26): 15798-802.
8. Chou TC, O'Connor OA, Tong WP, et al. The synthesis, discovery, and development of a highly promising class of microtubule stabilization agents: Curative effects of desoxyepothilones b and f against human tumor xenografts in nude mice. Proc Natl Acad Sci U S A 2001; 98(14); 8113-8.
9. Meng D, Su D-S, Balog A, et al. Remote effects in macrolide formation through ring-forming olefin metathesis: An application to the synthesis of fully active epothilone congeners. J Am Chem Soc 1997; 119: 2733-4.
10. Su D-S, Meng D, Bertinato P, et al. Total synthesis of (-) epothilone b: An extension of the suzuki coupling method and insights into structure-activity relationship of the epothilones. Angewandte Chemie Int'l. Ed. Engl. 1997; 36: 757-9.
11. Su D-S, Balog A, Meng D, et al. Structure-activity relationships of the epothilones and the first in vivo comparison with paclitaxel. Angewandte Chemie Int'l. Ed. Engl. 1998; 37: 2675-8.
12. Balog A, Harris CR, Savin K, Zhang X-G, Chou T-C, Danishefsky SJ. A novel aldol condensation with 2-methyl-4-pentenal and its application to an improved total synthesis of epothilone b. Angewandte Chemie Int'l. Ed. Engl. 1998; 37: 2675-8.
13. Harris CR, Danishefsky DJ. Complex target-oriented synthesis in the drug discovery process: A case history in the dEpoB series. J Org Chem 1999; 64: 8434-56.
14. Nicolaou KC, Ritzen A, Namoto K Recent developments in the chemistry, biology and medicine of the epothilones. Chem Commun (Camb) 2001; 17: 1523-35.
15. Julien B, Shah S. Heterologous expression of epothilone biosynthetic genes in myxococcus xanthus. Antimicrob Agents Chemother 2002; 46(9): 2772-8.
16. Arslanian RL, Parker CD, Wang PK, et al. Large-scale isolation and crystallization of epothilone d from myxococcus xanthus cultures. J Natural Products 2002; 65: 570-2.
17. Lee LF, Li G, Templeton DJ, Ting JP Paclitaxel (taxol)-induced gene expression and cell death are both mediated by the activation of c-jun nh2-terminal kinase (jnk/sapk). J Biol Chem 1998; 273(43): 28253-60.
18. MacKeigan JP, Collins TS, Ting JP. MEK inhibition enhances paclitaxel-induced tumor apoptosis. J Biol Chem 2000; 275(50): 38953-6.
19. McDaid HM, Horwitz SB. Selective potentiation of paclitaxel (taxol)-induced cell death by mitogen-activated protein kinase kinase inhibition in human cancer cell lines. Mol Pharmacol 2001; 60(2): 290-301.
20. Li CJ, Li YZ, Pinto AV, Pardee AB. Potent inhibition of tumor survival in vivo by beta-lapachone plus taxol: Combining drugs imposes different artificial checkpoints. Proc Natl Acad Sci U S A 1999; 96(23): 13369-74.
21. Juliano RL, Ling V. A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim Biophys Acta 1976; 455(1): 152-62.
22. Ueda K, Cardarelli C, Gottesman MM, Pastan I. Expression of a full-length cdna for the human "mdr1" gene confers resistance to colchicine, doxorubicin, and vinblastine. Proc Natl Acad Sci U S A 1987; 84(9): 3004-8.
23. Gottesman MM, Fojo T, Bates SE. Multidrug resistance in cancer: Role of atp-dependent transporters. Nat Rev Cancer 2002; 2(1): 48-58.
24. Greenberger LM, Lothstein L, Williams SS, Horwitz SB. Distinct p-glycoprotein precursors are overproduced in independently isolated drug-resistant cell lines. Proc Natl Acad Sci U S A 1988; 85(11): 3762-6.
25. Martello LA, McDaid HM, Regl DL, et al. Taxol and discodermolide represent a synergistic drug combination in human carcinoma cell lines. Clin Cancer Res 2000; 6(5): 1978-87.
26. Greco FA. Paclitaxel-based combination chemotherapy in advanced non-small cell lung cancer. Lung Cancer 2001; 34 Suppl 4: 553-6.
27. Marsden SP, Depew KM, Danishekfsy SJ. Stereoselective total synthesis of amauromine and 5-n-acetylardeemin. A concise route to the family of "reverse-prenylated" hexahydropyrroloindole alkaloids. J Am Chem Soc 1994; 116(24): 11143-4.
28. Boger DL, Soenen DR, Boyce CW, Hedrick MP, Jin Q. Total synthesis of ningalin b utilizing a heterocyclic azadiene diels-alder reaction and discovery of a new class of potent multidrug resistant (mdr) reversal agents. J Org Chem 2000; 65(8): 2479-83.
29. Kane RE, Black P. Glucose intolerance with low-, medium-, and high-carbohydrate formulas during nighttime enteral feedings in cystic fibrosis patients. J Pediatr Gastroenterol Nutr 1989; 8(3): 321-6.
30. Taxman DJ, MacKeigan JP, Clements C, Bergstralh DT, Ting JP. Transcriptional profiling of targets for combination therapy of lung carcinoma with paclitaxel and mitogen-activated protein/extracellular signal-regulated kinase kinase inhibitor. Cancer Res 2003; 63(16): 5095-104.
31. Yu C, Wang S, Dent P, Grant S. Sequence-dependent potentiation of paclitaxel-mediated apoptosis in human leukemia cells by inhibitors of the mitogen-activated protein kinase kinase/mitogen-activated protein kinase pathway. Mol Pharmacol 2001; 60(1): 143-54.
32. Alessi F, Quarta S, Savio M, et al. The cyclin-dependent kinase inhibitors olomoucine and roscovitine arrest human fibroblasts in g1 phase by specific inhibition of cdk2 kinase activity. Exp Cell Res 1998; 245(1): 8-18.
33. Jordan A, Hadfield JA, Lawrence NJ, McGown AT. Tubulin as a target for anticancer drugs: Agents which interact with the mitotic spindle. Med Res Rev 1998; 18(4): 259-96.
34. Ling YH, Yang Y, Tornos C, Singh B, Perez-Soler R. Paclitaxel-induced apoptosis is associated with expression and activation of c-mos gene product in human ovarian carcinoma skov3 cells. Cancer Res 1998; 58(16): 3633-40.
35. Liu QY, Stein CA. Taxol and estramustine-induced modulation of human prostate cancer cell apoptosis via alteration in bcl-xl and bak expression. Clin Cancer Res 1997; 3(11): 2039-46.
36. Moos PJ, Fitzpatrick FA. Taxane-mediated gene induction is independent of microtubule stabilization: Induction of transcription regulators and enzymes that modulate inflammation and apoptosis. Proc Natl Acad Sci U S A 1998; 95(7): 3896-901.
37. Lee LF, Haskill JS, Mukaida N, Matsushima K, Ting JP. Identification of tumor-specific paclitaxel (taxol)-responsive regulatory elements in the interleukin-8 promoter. Mol Cell Biol 1997; 17(9): 5097-105.
38. Lee LF, Schuerer-Maly CC, Lofquist AK, et al. Taxol-dependent transcriptional activation of il-8 expression in a subset of human ovarian cancer. Cancer Res 1996; 56(6): 1303-8.
39. Wiese S, Emmerich D, Schroder B, et al. The novel human hnf-3/fork head-like 5 gene: Chromosomal localization and expression pattern. DNA Cell Biol 1997; 16(2): 165-71.
40. Burgering BM, Kops GJ. Cell cycle and death control: Long live forkheads. Trends Biochem Sci 2002; 27(7): 352-60.
41. Raymond E, Soria JC, Izbicka E, Boussin F, Hurley L, Von Hoff DD. DNA g-quadruplexes, telomere-specific proteins and telomere-associated enzymes as potential targets for new anticancer drugs. Invest New Drugs 2000; 18(2): 123-37.
42. Van Seuningen I, Pigny P, Perrais M, Porchet N, Aubert JP. Transcriptional regulation of the 11p15 mucin genes. Towards new biological tools in human therapy, in inflammatory diseases and cancer? Front Biosci 2001; 6: D1216-34.
43. Moss ML, White JM, Lambert MH, Andrews RC. Tace and other adam proteases as targets for drug discovery. Drug Discov Today 2001; 6(8): 417-26.
44. Fairchild CR, Ivy SP, Kao-Shan CS, et al. Isolation of amplified and overexpressed DNA sequences from adriamycin-resistant human breast cancer cells. Cancer Res 1987; 47(19): 5141-8.
45. Chou TC, Depew KM, Zheng YH, et al. Reversal of anticancer multidrug resistance by the ardeemins. Proc Natl Acad Sci U S A 1998; 95(14): 8369-74.
46. Long BH, Fairchild CR. Paclitaxel inhibits progression of mitotic cells to g1 phase by interference with spindle formation without affecting other microtubule functions during anaphase and telephase. Cancer Res 1994; 54(16): 4355-61.
47. MacKeigan JP, Taxman DJ, Hunter D, Earp HS, 3rd, Graves LM, Ting JP. Inactivation of the antiapoptotic phosphatidylinositol 3-kinase-akt pathway by the combined treatment of taxol and mitogen-activated protein kinase kinase inhibition. Clin Cancer Res 2002; 8(7): 2091-9.
48. Cross SM, Sanchez CA, Morgan CA, et al. A p53-dependent mouse spindle checkpoint. Science 1995; 267(5202): 1353-6.
49. Di Leonardo A, Khan SH, Linke SP, Greco V, Seidita G, Wahl GM. DNA rereplication in the presence of mitotic spindle inhibitors in human and mouse fibroblasts lacking either p53 or prb function. Cancer Res 1997; 57(6): 1013-9.
50. Lanni JS, Jacks T. Characterization of the p53-dependent postmitotic checkpoint following spindle disruption. Mol Cell Biol 1998; 18(2): 1055-64.
51. Ogretmen B, Safa AR. Expression of the mutated p53 tumor suppressor protein and its molecular and biochemical characterization in multidrug resistant mcf-7/adr human breast cancer cells. Oncogene 1997; 14(4): 499-506.
52. Torres K, Horwitz SB. Mechanisms of taxol-induced cell death are concentration dependent. Cancer Res 1998; 58(16): 3620-6.
53. Arcamone F, Animati F, Berettoni M, et al. Doxorubicin disaccharide analogue: Apoptosis-related improvement of efficacy in vivo. J Natl Cancer Inst 1997; 89(16): 1217-23.
54. Koh J, Kubota T, Migita T, et al. Ucn-01 (7-hydroxystaurosporine) inhibits the growth of human breast cancer xenografts through disruption of signal transduction. Breast Cancer 2002; 9(1): 50-4.
55. Blagosklonny MV and Fojo T Molecular effects of paclitaxel: Myths and reality (a critical review). Int J Cancer 1999; 83(2): 151-6.