Peloruside A does not bind to the taxoid site on β-tubulin and retains its activity in multidrug-resistant cell lines

Cancer Research

Volumn 64, Issue 15, 2004, Pages 5063-5067

  Gaitanos, Thomas N ^a   Buey, Rubén M ^b   Fernando Diaz J ^b   Northcote, Peter T ^a   Teesdale Spittle, Paul ^a   Andreu, José M ^b   Miller, John H ^a  

^a VICTORIA UNIVERSITY OF WELLINGTON   (New Zealand)

^b CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA TUBULIN; DOCETAXEL; EPOTHILONE B; GLYCOPROTEIN P; LAULIMALIDE; MICROTUBULE ASSOCIATED PROTEIN; NATURAL PRODUCT; PACLITAXEL; PACLITAXEL DERIVATIVE; PELORUSIDE A; TAXOID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING COMPETITION; BINDING SITE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CYTOTOXICITY; GENE MUTATION; GENE OVEREXPRESSION; HUMAN; HUMAN CELL; IN VITRO STUDY; MICROTUBULE ASSEMBLY; MULTIDRUG RESISTANCE; NONHUMAN; PRIORITY JOURNAL; PROTEIN PURIFICATION; PROTEIN TRANSPORT; SPONGE (PORIFERA);

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BICYCLO COMPOUNDS, HETEROCYCLIC; CELL DIVISION; CELL LINE; CHO CELLS; CRICETINAE; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; FEMALE; GENES, MDR; HUMANS; LACTONES; LIGANDS; MASS SPECTROMETRY; MICROTUBULES; MUTATION; OVARIAN NEOPLASMS; P-GLYCOPROTEIN; PACLITAXEL; TAXOIDS; TUBULIN;

EID: 3442894416     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-04-0771     Document Type: Article

References (24)

1. West LM, Northcote PT, Battershill CN. Peloruside A: a potent cytotoxic macrolide isolated from the New Zealand marine sponge Mycale sp. J Org Chem 2000;65:445-9.
2. Hood KA, Bäckström BT, West LM, Northcote PT, Berridge MV, Miller JH. The novel cytotoxic sponge metabolite peloruside A, structurally similar to bryostatin-1, has unique bioactivity independent of protein kinase C. Anticancer Drug Des 2001;16:155-66.
3. Liao X, Wu Y, De Brabander JK. Total synthesis and absolute configuration of the novel microtubule-stabilizing agent peloruside A. Angew Chem Int Ed Engl 2003;42:1648-52.
4. Hood KA, West LM, Rouwé B, et al. Peloruside, a novel anti-mitotic agent with paclitaxel-like microtubule-stabilizing activity. Cancer Res 2002;62:3356-60.
5. Stachel SJ, Biswas K, Danishefsky J. The epothilones, eleutherobins, and related types of molecules. Curr Pharmaceut Design 2001;7:1277-90.
6. Rowinsky EK, Eisenhauer EA, Chaudhry V, Arbuck SG, Donehower RC. Clinical toxicities encountered with paclitaxel (Taxol). Semin Oncol 1993;20:1-15.
7. Parekh H, Wiesen K, Simpkins H. Acquisition of Taxol resistance via P-glycoprotein-and non-P-glycoprotein-mediated mechanisms in human ovarian carcinoma cells. Biochem Pharmacol 1997;53:461-70.
8. Giannakakou P, Sackett D, Kang Y, et al. Paclitaxel-resistant human ovarian cancer cells have mutant β-tubulins that exhibit impaired paclitaxel-driven polymerization. J Biol Chem 1997;272:17118-25.
9. Giannakakou P, Gussio R, Nogales E, et al. A common pharmacophore for epothilone and taxanes: molecular basis for drug resistance conferred by tubulin mutations in human cancer cells. Proc Natl Acad Sci USA 2000;97:2904-9.
10. 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). J Biol Chem 1997;272:2534-41.
11. Pryor DE, O'Brate A, Bilcer G, et al. The microtubule stabilizing agent laulimalide does not bind in the taxoid site, kills cells resistant to paclitaxel and epothilones. and may not require its epoxide moiety for activity. Biochemistry 2002;41:9109-15.
12. 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;55:2325-33.
13. Kowalski RJ, Giannakakou P, Gunasekera P, Longley RE, Day BW, Hamel E. The microtubule-stabilizing agent discodermolide competitively inhibits the binding of paclitaxel (Taxol) to tubulin polymers, enhances tubulin nucleation reactions more potently than paclitaxel, and inhibits the growth of paclitaxel-resistant cells. Mol Pharmacol 1997;52:613-22.
14. Mooberry SL, Tien G, Hernandez AH, Plubrukarn A, Davidson BS. Laulimalide and isolaulimalide, new paclitaxel-like microtubule-stabilizing agents. Cancer Res 1999;59:653-60.
15. Ling V, Thompson LH. Reduced permeability in CHO cells as a mechanism of resistance to colchicine. J Cell Physiol 1973;83:103-16.
16. Diaz JF, Andren JM. Assembly of purified GDP-tubulin into microtubules induced by Taxol and taxotere: reversibility, ligand stoichiometry, and competition. Biochemistry 1993;32:2747-55.
17. Oosawa F, Asakura S. Thermodynamics of the polymerization of protein. London: Academic Press; 1975.
18. Andreu JM, Timasheff SN. The measurement of cooperative protein self-assembly by turbidity and other techniques. Methods Enzymol 1986;130:47-59.
19. Díaz JF, Strobe R, Engelborghs Y, Souto AA, Andreu JM. Molecular recognition of Taxol by microtubules. Kinetics and thermodynamics of binding of fluorescent Taxol derivatives to an exposed site. J Biol Chem 2000;275:26265-76.
20. Andreu JM, Barasoain I. The interaction of baccatin III with the Taxol binding site of microtubules determined by a homogeneous assay with fluorescent taxoid. Biochemistry 2001;40:11975-84.
21. Nicolaou KC, Ritzen A, Namoto K, et al. Chemical synthesis and biological evaluation of novel epothilone B and trans-12,13-cyclopropyl epothilone B analogues. Tetrahedron 2002;58:6413-32.
22. Buey RM, Díaz JF, Andreu JM, et al. Energetics of interaction of C12, cyclopropyl and C15 side chain epothilone analogs with the paclitaxel binding site. Relationship between binding affinity, microtubule stabilization and cytotoxicity. Chem Biol 2004;11:225-36.
23. Andreu JM, Díaz JF, Gil R, et al. Solution structure of taxotere-induced microtubules to 3-nm resolution. The change in protofilament number is linked to the binding of the Taxol side chain. J Biol Chem 1994;269:31785-92.
24. He L, Yang C-PH, Horwitz SB. Mutations in β-tubulin map to domains involved in regulation of microtubule stability in epothilone-resistant cell lines. Mol Cancer Ther 2001;1:3-10.