Structure-activity profiles of eleutherobin analogs and their cross- resistance in Taxol-resistant cell lines

Cancer Chemotherapy and Pharmacology

Volumn 44, Issue 2, 1999, Pages 131-137

  McDaid, Hayley M ^a   Bhattacharya, Samit K ^b   Chen, Xiao Tao ^b   He, Lifeng ^a   Shen, Heng Jia ^a   Gutteridge, Clare E ^b   Horwitz, Susan Band ^a   Danishefsky, Samuel J ^b,c  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

^b Havemeyer Hall ^*  (United States)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

Drug resistance; Eleutherobin; Microtubules; Structure activity; Taxol

Indexed keywords

ANTIMITOTIC AGENT; ELEUTHEROBIN; GLYCOPROTEIN P; GUANOSINE TRIPHOSPHATE; MICROTUBULE PROTEIN; NEOELEUTHEROBIN; PACLITAXEL; SKBII 13; SKBII 294; SKBII 296; SKBII 298; TUBULIN; UNCLASSIFIED DRUG; UROCANIC ACID;

ANIMAL CELL; ARTICLE; CELL LINE; CELL STRAIN 3T3; CONTROLLED STUDY; CROSS RESISTANCE; CYTOTOXICITY; DRUG SENSITIVITY; HUMAN; HUMAN CELL; LUNG NON SMALL CELL CANCER; MACROPHAGE; MICROTUBULE ASSEMBLY; MOUSE; NONHUMAN; OVARY CARCINOMA; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

ALKALOIDS; ANTINEOPLASTIC AGENTS; CALCIUM; DITERPENES; DRUG RESISTANCE, NEOPLASM; HUMANS; MICROTUBULES; P-GLYCOPROTEIN; PACLITAXEL; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUMOR CELLS, CULTURED;

EID: 0032988620     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002800050957     Document Type: Article

References (32)

1. 1. Bogdan C, Ding A (1992) Taxol, a microtubule-stabilizing antineoplastic agent, induces expression of tumor necrosis factor alpha and interleukin-1 in macrophages. J Leukoc Biol 52: 119
2. 2. Bollag DM, McQueney PA, Zhu J, Hensens O, Koupal L, Liesch J, Goetz M, Lazarides E, Woods CM (1996) Epothilones, a new class of microtubule-stabilizing agents with a Taxol-like mechanism of action. Cancer Res 55: 2325
3. 3. Bradley G, Naik M, Ling V (1989) P-glycoprotein expression in multidrug-resistant human ovarian carcinoma cell lines. Cancer Res 49: 2790
4. 4. Burkhart CA, Berman JW, Swindell CS, Horwitz SB (1994) Relationship between the structure of Taxol and other taxanes on induction of tumor necrosis factor - α gene expression and cytotoxicity. Cancer Res 54: 5779
5. 5. Chen XT, Gutteridge CE, Bhattacharya SK, Zhou B, Pettus TRR, Hascall T, Danishefsky SJA (1998) A convergent route for the total synthesis of the Eleuthesides. Angew Chem Int Ed Engl 37: 185
6. 6. Chen XT, Zhou B, Bhattacharya SK, Gutteridge CE, Pettus TRR, Danishefsky SJ (1998) The total synthesis of Eleutherobin: a surprise ending. Angew Chem Int Ed Engl 110: 789
7. 7. Ding AH, Porteu F, Sanchez E, Nathan CF (1990) Shared actions of endotoxin and Taxol on TNF receptors and TNF release. Science 248: 370
8. 8. Dustin P (1984) Microtubules, 2nd edn. Springer-Verlag, Berlin, p 482
9. 9. Gottesman M, Pastan I (1993) Biochemistry of multidrug resistance mediated by the multidrug transporter. Annu Rev Biochem 62: 385
10. 10. Haar E ter, Kowalski RJ, Lin CM, Longley RE, Gunasekera SP, Rosenkranz HS, Day BW (1996) Discoderomolide, a cytotoxic marine agent that stabilizes microtubules more potently than Taxol. Biochemistry 35: 243
11. 11. Hung DT, Chen J, Schreiber SL (1996) (+)-Discodermolide binds to microtubules in stoichiometric ratio to tubulin dimers, blocks Taxol binding and results in mitotic arrest. Chem Biol 3: 287
12. 12. Jordan MA, Toso RJ, Thrower D, Wilson L (1993) Mechanism of mitotic block and inhibition of cell proliferation by taxol at low concentrations. Proc Natl Acad Sci USA 90: 9552
13. 13. Kavallaris M, Kuo DYS, Burkhart CA, Lee Regl D, Norris MD, Haber M, Horwitz SB (1997) Taxol-resistant epithelial ovarian tumors are associated with altered expression of specific β-tubulin isotypes. J Clin Invest 100: 1282
14. 14. Lindel T, Jensen PR, Fenical W, Long BH, Casazza AM, Carboni J, Fairchild CR (1997) Eleutherobin, a new cytotoxin that mimics paclitaxel (Taxol) by stabilizing microtubules. J Am Chem Soc 119: 8744
15. 15. Liu Y, Bhalla K, Hill C, Priest DG (1994) Evidence for involvement of tyrosine phosphorylation in taxol-induced apoptosis in a human ovarian tumor cell line. Biochem Pharmacol 48: 1265
16. 16. Long BH, Carboni JM, Wasserman AJ, Cornell LA, Casazza AM, Jensen PR, Lindel T, Fenical W, Fairchild CR (1998) Eleutherobin, a novel cytotoxic agent that induces tubulin polymerization, is similar to paclitaxel (Taxol). Cancer Res 58: 1111
17. 17. Nicolaou KC, vanDelft F, Ohshima T, Vourloumis D, Xu J, Hosokawa S, Pfefferkorn J, Kim S, Li T (1997) Total synthesis of eleutherobin. Angew Chem Int Ed Engl 36: 2520
18. 18. Nicolaou KC, Vourloumis D, Li T, Pastor J, Winssinger N, He Y, Nikovic S, Sarabia F, Vallberg H, Roschaogar F, King NP, Finlay MRV, Giannakakou P, Verdier-Pinard P, Hamel E (1997) Designed epothilones: combinatorial synthesis, tubulin assembly properties, and cytotoxic action against Taxol-resistant tumor cells. Angew Chem Int Ed Engl 36: 2097
19. 19. Nicolaou KC, Xu JY, Kim S, Ohshima T, Hosokawa S, Pfefferkorn J (1997) Synthesis of the tricyclic core of eleutherobin and sarcodictyins and total synthesis of sarcodictyin A. J Am Chem Soc 119: 11353
20. 20. Nicolaou KC, Kim S, Pfefferkorn J, Xu J, Ohshima T, Hosokawa S, Vourloumis D, Li T (1998) Synthesis and biological activity of sarcodictyins. Angew Chem Int Ed Engl 37: 1418
21. 21. Rao S, Krauss NE, Heerding JM, Swindel CS, Ringel I, Orr GA, Horwitz SB (1994) 3′-(p-azidobenzamido) taxol photolabels the N-terminal 31 amino-acids of β-tubulin. J Biol Chem 269: 3131
22. 22. Rao S, Orr GA, Chaudhary AG, Kingston DGI, Horwitz SB (1995) Characterization of the Taxol-binding site on the microtubule: 2-(m-azidobenzoyl) taxol photolabels a peptide (amino acids 217-231) of β-tubulin. J Biol Chem 270: 20235
23. 23. Rowinsky EK, Donehower RC, Jones RJ, Tucker RW (1988) Microtubule changes and cytotoxicity in leukemic cell lines treated with Taxol. Cancer Res 48: 4093
24. 24. Roy SN, Horwitz SB (1985) A phosphoglycoprotein associated with Taxol resistance in J774.3 cells. Cancer Res 45: 3856
25. 25. Schiff PB, Horwitz SB (1980) Taxol stabilizes microtubules in mouse fibroblast cells. Proc Natl Acad Sci USA 77: 1561
26. 26. Schiff PB, Fant J, Horwitz SB (1979) Promotion of microtubule assembly in vitro by taxol. Nature 277: 665
27. 27. Su D-S, Balog A, Meng D, Bertinato P, Danishefsky SJ, Zheng Y-H, Chou T-C, He L, Horwitz SB (1997) Structure-activity relationships of the epothilones and the first in vivo comparison with paclitaxel. Angew Chem Int Ed Engl 36: 2093
28. 28. Torres K, Horwitz SB (1998) Mechanisms of Taxol-induced cell death are concentration dependent. Cancer Res 58: 3620
29. 29. Wang T-H, Wang H-S, Ichijo H, Giannakakou P, Foster JS, Fojo T, Wimalasena J (1998) Microtubule-interfering agents activate c-jun N-terminal kinase/stress-activated kinase through both ras and apoptosis signal-regulating kinase pathways. J Biol Chem 273: 4928
30. 30. Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT (1971) Plant antitumor agents: VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 93: 2325
31. 31. Weisenberg RC (1972) Microtubule formation in vitro in solutions containing low calcium concentrations. Science 177: 1104
32. 32. Wolfson M, Huang Yang CP, Horwitz SB (1997) Taxol induces tyrosine phosphorylation of SHC and its association with GRB2 in murine RAW 264.7 cells. Int J Cancer 70: 248