The molecular pharmacology of symplostatin 1: A new antimitotic dolastatin 10 analog

International Journal of Cancer

Volumn 104, Issue 4, 2003, Pages 512-521

  Mooberry, Susan L ^a   Leal, Rachel M ^a   Tinley, Tina L ^a   Luesch, Hendrik ^b   Moore, Richard E ^b   Corbett, Thomas H ^c  

^a SOUTHWEST FOUNDATION FOR BIOMEDICAL RESEARCH   (United States)

^b UNIVERSITY OF HAWAII   (United States)

^c WAYNE STATE UNIVERSITY   (United States)

Author keywords

Drug discovery; Microtubules; Natural products; Tubulin

Indexed keywords

ANTIMITOTIC AGENT; CASPASE 3; DOLASTATIN 10; PROTEIN BCL 2; SYMPLOSTATIN 1; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; APOPTOSIS; ARTICLE; CELL CYCLE; CELL INVASION; CELL PROLIFERATION; CONTROLLED STUDY; CYANOBACTERIUM; DRUG EFFICACY; DRUG ISOLATION; DRUG MECHANISM; DRUG TARGETING; DRUG TOLERABILITY; ENDOTHELIUM CELL; ENZYME ACTIVATION; FEMALE; HUMAN; HUMAN CELL; IC 50; INTERPHASE; METAPHASE; MICRONUCLEUS; MICROTUBULE ASSEMBLY; MITOSIS SPINDLE; MOUSE; NEOVASCULARIZATION (PATHOLOGY); NONHUMAN; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; SIGNAL TRANSDUCTION; SOLID TUMOR; SYMPLOCA;

ANIMALS; ANTINEOPLASTIC AGENTS; CASPASE 3; CASPASES; CELL NUCLEUS; CELLS, CULTURED; DEPSIPEPTIDES; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; ENDOTHELIUM, VASCULAR; HUMANS; INTERPHASE; MICE; MICE, INBRED C57BL; MICROTUBULES; MITOSIS; MITOTIC SPINDLE APPARATUS; NEOPLASMS, EXPERIMENTAL; OLIGOPEPTIDES; PHOSPHORYLATION; PROTO-ONCOGENE PROTEINS C-BCL-2; RATS; TUBULIN;

EID: 0037457479     PISSN: 00207136     EISSN: None     Source Type: Journal    
DOI: 10.1002/ijc.10982     Document Type: Article

References (44)

1. ter Haar E, Kowalski RJ. Hamel E, Lin CM, Longley RE, Gunasekera SP, Rosenkranz HS, Day BW. Discodermolide, a cytotoxic marine agent that stabilizes microtubules more potently than taxol. Biochemistry 1996;35:243-50.
2. Lindel T, Jensen PR, Fenical W, Long BH, Casazza AM, Carboni J, Fairchild CR. Eleutherobin, a new cytotoxin that mimics paclitaxel (Taxol) by stabilizing microtubules. J Am. Chem. Soc 1997;119:8744-45.
3. 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.
4. Bai RL, Paull KD, Herald CL, Malspeis L, Pettit GR, Hamel E. Halichondrin B and homohalichondrin B, marine natural products binding in the vinca domain of tubulin. Discovery of tubulin-based mechanism of action by analysis of differential cytotoxicity data. J Biol Chem 1991;266:15882-9.
5. Bai R, Pettit GR, Hamel E. Dolastatin 10, a powerful cytostatic peptide derived from a marine animal. Inhibition of tubulin polymerization mediated through the vinca alkaloid binding domain. Biochem Pharmacol 1990;39:1941-9.
6. Pettit GR. The dolastatins. Fortschr Chem Org Naturst 1997;70:1-79.
7. Luesch H, Moore RE, Paul VJ, Mooberry SL, Corbett TH. Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1. J Nat Prod 2001;64:907-10.
8. Beckwith M, Urba WJ, Longo DL. Growth inhibition of human lymphoma cell lines by the marine products, dolastatins 10 and 15. J Natl Cancer Inst 1993;85:483-8.
9. Pitot HC, McElroy EA, Jr, Reid JM, Windebank AJ, Sloan JA, Erlichman C, Bagniewski PG, Walker DL, Rubin J, Goldberg RM, Adjei AA, Ames MM. Phase I trial of dolastatin-10 (NSC 376128) in patients with advanced solid tumors. Clin Cancer Res 1999;5:525-31.
10. Madden T, Tran HT, Beck D, Huie R, Newman RA, Pusztai L, Wright JJ, Abbruzzese JL. Novel marine-derived anticancer agents: a phase I clinical, pharmacological, and pharmacodynamic study of dolastatin 10 (NSC 376128) in patients with advanced solid tumors. Clin Cancer Res 2000;6:1293-301.
11. Margolin K, Longmate J, Synold TW, Gandara DR, Weber J,. Gonzalez R, Johansen MJ, Newman R, Baratta T, Doroshow JH. Dolastatin-10 in metastatic melanoma: a phase II and pharmokinetic trial of the California Cancer Consortium. Invest New Drugs 2001;19:335-40.
12. Krug LM, Miller VA, Kalemkerian GP, Kraut MJ, Ng KK, Heelan RT, Pizzo BA, Perez W, McClean N, Kris MG. Phase II study of dolastatin-10 in patients with advanced non-small-cell lung cancer. Ann Oncol 2000;11:227-8.
13. Vaishampayan U, Glode M, Du W, Kraft A, Hudes G, Wright J, Hussain M. Phase II study of dolastatin-10 in patients with hormone-refractory metastatic prostate adenocarcinoma. Clin Cancer Res 2000;6:4205-8.
14. Watanabe J, Natsume T, Fujio N, Miyasaka K, Kobayashi M. Induction of apoptosis in human cancer cells by TZT-1027, an antimicrotubule agent. Apoptosis 2000;5:345-53.
15. Harrigan GG, Luesch H, Yoshida WY, Moore RE, Nagle DG, Paul VJ, Mooberry SL, Corbett TH, Valeriote FA. Symplostatin 1: A dolastatin 10 analogue from the marine cyanobacterium Symploca hydnoides. J Nat Prod 1998;61:1075-7.
16. Scudiero DA, Monks A, Sausville EA. Cell line designation change: multidrug-resistant cell line in the NCI anticancer screen. J Natl Cancer Inst 1998;90:862.
17. Fairchild CR, Ivy SP, Kao-Shan CS, Whang-Peng J, Rosen N, Israel MA, Melera PW, Cowan KH, Goldsmith ME. Isolation of amplified and overexpressed DNA sequences from adriamycin-resistant human breast cancer cells. Cancer Res 1987;47:5141-5148.
18. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H. Kenney S, Boyd MR. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990;82:1107-12.
19. Boyd MR, Paull KD. Some practical considerations and applications of the National Cancer Institute in vitro anticancer discovery screen. Drug Dev Res 1995;34:91-109.
20. Mooberry SL, Busquets L, Tien G. Induction of apoptosis by cryptophycin 1, a new antimicrotubule agent. Int J Cancer 1997;73:440-8.
21. Wakabayashi H, Nicolson GL. Transfilter cell invasion assays. In: Cells JE. ed. Cell Biology: A Laboratory Handbook. vol. 1, 2nd ed. San Diego: Academic Press, 1998. p 296-301.
22. Corbett T, Valeriote F, LoRusso P, Polin L, Panchapor C, Pugh S, Panchapor C, Pugh S, White K, Knight J, Demchik L, Jones J, et al. In vivo methods for screening and preclinical testing. In: Teicher B. Anticancer drug development guide: preclinical screening, clinical trials, and approval. Totowa, NJ: Humana Press, Inc., 1997. p 75-99.
23. 1 phase of the cell cycle, and specific-related mortality of transformed cells. J Cell Biol 1996;135:689-700.
24. Blagosklonny MV. Cell death beyond apoptosis. Leukemia 2000;14:1502-8.
25. Earnshaw WC, Martins LM, Kaufmann, S. H. Mammalian caspases: structure, activation, substrates, and functions during apoptosis. Annu Rev Biochem 1999;68:383-424.
26. Haldar S, Basu A, Croce CM. Bcl2 is the guardian of microtubule integrity. Cancer Res. 1997;57:229-33.
27. Blagosklonny, M. V. Unwinding the loop of Bcl-2 phosphorylation. Leukemia 2001;15:869-874.
28. Miller KD, Sweeney CJ, Sledge GW, Jr. Redefining the target: chemotherapeutics as antiangiogenics. J Clin Oncol 2001;19:1195-206.
29. Vacca A, Iurlaro M, Ribatti D, Minischetti M, Nico B, Ria R, Pellegrino A, Dammacco F. Antiangiogenesis is produced by nontoxic doses of vinblastine. Blood 1999;94:4143-55.
30. Belotti D, Vergani V, Drudis T, Borsotti P, Pitelli MR, Viale G, Giavazzi R, Taraboletti G. The microtubule-affecting drug paclitaxel has antiangiogenic activity. Clin Cancer Res 1996;2:1843-9.
31. Toppmeyer DL, Slapak CA, Croop J, Kufe DW. Role of P-glycoprotein in dolastatin 10 resistance. Biochem Pharmacol 1994;48:609-12.
32. Smith CD, Zhang X, Mooberry SL, Patterson GM, Moore RE. Cryptophycin: a new antimicrotubule agent active against drug-resistant cells. Cancer Res 1994;54:3779-84.
33. Wilson L, Jordan MA. Microtubule dynamics: taking aim at a moving target. Chem Biol 1995;2:569-73.
34. Jordan, M. A. Mechanism of action of antitumor drugs that interact with microtubules and tubulin. Curr Med Chem-Anti-Cancer Agents 2002;2:1-17.
35. Rusan NM, Fagerstrom CJ, Yvon AM, Wadsworth P. Cell cycle-dependent changes in microtubule dynamics in living cells expressing green fluorescent protein-alpha tubulin. Mol. Biol. Cell 2001;12:971-80.
36. Haldar S, Jena N, Croce CM. Inactivation of Bcl-2 by phosphorylation. Proc Natl Acad Sci USA 1995;92:4507-11.
37. Blagosklonny MV, Fojo T. Molecular effects of paclitaxel: myths and reality [a critical review]. Int J Cancer 1999;83:151-6.
38. Natsume T, Watanabe J, Tamaoki S, Fujio N, Miyasaka K, Kobayashi M. Characterization of the interaction of TZT-1027, a potent antitumor agent, with tubulin. Jpn J Cancer Res 2000;91:737-47.
39. Bai RL, Pettit GR, Hamel E. Binding of dolastatin 10 to tubulin at a distinct site for peptide antimitotic agents near the exchangeable nucleotide and vinca alkaloid sites. J Biol Chem 1990;265:17141-9.
40. Folkman J. What is the evidence that tumors are angiogenesis dependent? J Natl Cancer Inst. 1990;82:4-6.
41. Klauber N, Parangi S, Flynn E, Hamel E, D'Amato RJ. Inhibition of angiogenesis and breast cancer in mice by the microtubule inhibitors 2-methoxyestradiol and taxol. Cancer Res. 1997;57:81-6.
42. Otani M, Natsume T, Watanabe JI, Kobayashi M, Murakoshi M, Mikami T, Nakayama T. TZT-1027, an antimicrotubule agent, attacks tumor vasculature and induces tumor cell death. Jpn J Cancer Res 2000;91:837-44.
43. Luesch H, Yoshida WY, Moore RE, Paul VJ, Mooberry SL, Corbett TH. Symplostatin 3, a new dolastatin I0 analogue from the marine cyanobacterium Symploca sp. VP452. J Nat Prod 2002;65:16-20.
44. O'Connor PM, Jackman J, Bae I, Myers TG, Fan S, Mutoh M, Scudiero DA, Monks A, Sausville EA, Weinstein JN. Friend S, Fornace AJ Jr, et al. Characterization of the p53 tumor suppressor pathway in cell lines of the National Cancer Institute anticancer drug screen and correlations with the growth-inhibitory potency of 123 anticancer agents. Cancer Res 1997;57:4285-300.