Cyclic depsipeptides as potential cancer therapeutics

Anti-Cancer Drugs

Volumn 26, Issue 3, 2015, Pages 259-271

  Kitagaki, Jirouta ^a,b   Shi, Genbin ^c   Miyauchi, Shizuka ^a   Murakami, Shinya ^a   Yang, Yili ^d  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY DENTAL HOSPITAL   (Japan)

^c NATIONAL CANCER INSTITUTE   (United States)

^d SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

aplidine; cancer therapy; cryptophycin 1; cyclic depsipeptides; kahalalide F; LY355703; PM02734; romidepsin

Indexed keywords

ANTINEOPLASTIC AGENT; ARENASTATIN A; BEAUVERICIN; BORTEZOMIB; CELOGENTIN; CRYPTOPHYCIN 1; CRYPTOPHYCIN 52; CYCLODEPSIPEPTIDE; CYCLOPHOSPHAMIDE; DEHYDRODIDEMNIN B; DEPSIPEPTIDE; DEXAMETHASONE; DIDEMNIN B; ECHINOMYCIN; ELISIDEPSIN; ENNIATIN; ERLOTINIB; FLUOROURACIL; KAHALALIDE F; KORKORMICIN A; LUZOPEPTIN; MITOMYCIN; NEAMPHAMIDE; PAECILODEPSIPEPTIDE; ROMIDEPSIN; SANSALVAMIDE A; THIOCORALINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALINOMYCIN; VINCRISTINE; DIDEMNINS; HISTONE DEACETYLASE INHIBITOR; LACTAM; LACTONE;

ADVANCED CANCER; ALOPECIA; ANAPLASTIC THYROID CANCER; ANEMIA; ANOREXIA; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; BREAST CANCER; CANCER CHEMOTHERAPY; CHEMOTHERAPY INDUCED EMESIS; COLON CARCINOMA; COLORECTAL CANCER; CUTANEOUS T CELL LYMPHOMA; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG ERUPTION; DRUG FEVER; DRUG HALF LIFE; DRUG INDUCED HEADACHE; DRUG STRUCTURE; ENZYME INHIBITION; FATIGUE; FIBROSARCOMA; GRANULOCYTOPENIA; HUMAN; KIDNEY CARCINOMA; LARGE CELL CARCINOMA; LEUKEMIA; LEUKOPENIA; LEWIS CARCINOMA; LUNG CANCER; LYMPHOCYTOPENIA; LYMPHOMA; MAXIMUM PLASMA CONCENTRATION; MELANOMA; MULTIPLE MYELOMA; MYALGIA; MYELOMA; NAUSEA; NEUROPATHY; NEUTROPENIA; NON SMALL CELL LUNG CANCER; NONHUMAN; OVARY CANCER; OVARY CARCINOMA; PERIPHERAL T CELL LYMPHOMA; PRIORITY JOURNAL; PROSTATE CANCER; RETICULOSARCOMA; REVIEW; SIDE EFFECT; SMALL CELL LUNG CANCER; STOMACH ADENOCARCINOMA; STOMACH CARCINOMA; THROMBOCYTOPENIA; THYROID MEDULLARY CARCINOMA; ANIMAL; CLINICAL TRIAL (TOPIC); LYMPHOMA, T-CELL, CUTANEOUS;

ANIMALS; ANTINEOPLASTIC AGENTS; CLINICAL TRIALS AS TOPIC; DEPSIPEPTIDES; HISTONE DEACETYLASE INHIBITORS; HUMANS; LACTAMS; LACTONES; LYMPHOMA, T-CELL, CUTANEOUS;

EID: 84925506096     PISSN: 09594973     EISSN: 14735741     Source Type: Journal    
DOI: 10.1097/CAD.0000000000000183     Document Type: Review

References (127)

1. Gaumann E, Roth S, Ettlinger L, Plattner P, Nager U. Ionophore antibiotics produced by the fungus Fusarium orthoceras var. ennitum and other. Experientia 1947; 3:202.
2. Hwang Y, Rowley D, Rhodes D, Gertsch J, Fenical W, Bushman F. Mechanism of inhibition of a poxvirus topoisomerase by the marine natural product sansalvamide A. Mol Pharmacol 1999; 55:1049-1053.
3. Isaka M, Palasarn S, Lapanun S, Sriklung K. Paecilodepsipeptide A, an antimalarial and antitumor cyclohexadepsipeptide from the insect pathogenic fungus Paecilomyces cinnamomeus BCC 9616. J Nat Prod 2007; 70:675-678.
4. Tonshin AA, Teplova VV, Andersson MA, Salkinoja-Salonen MS. The Fusarium mycotoxins enniatins and beauvericin cause mitochondrial dysfunction by affecting the mitochondrial volume regulation, oxidative phosphorylation and ion homeostasis. Toxicology 2010; 276:49-57.
5. Kobayashi J, Suzuki H, Shimbo K, Takeya K, Morita H. Celogentins A-C, new antimitotic bicyclic peptides from the seeds of Celosia argentea. J Org Chem 2001; 66:6626-6633.
6. Ma B, Banerjee B, Litvinov DN, He L, Castle SL. Total synthesis of the antimitotic bicyclic peptide celogentin C. J Am Chem Soc 2010; 132:1159-1171.
7. Matsumoto T, Shishido A, Morita H, Itokawa H, Takeya K. Cyclolinopeptides F-I, cyclic peptides from linseed. Phytochemistry 2001; 57:251-260.
8. Urdiales JL, Morata P, Núñez De Castro I, Sánchez-Jiménez F. Antiproliferative effect of dehydrodidemnin B (DDB), a depsipeptide isolated from Mediterranean tunicates. Cancer Lett 1996; 102:31-37.
9. Hamann MT, Scheuer PJ. Kahalalide F: a bioactive depsipeptide from the sacoglossan mollusk Elysia rufescens and the green alga Bryopsis sp. J Am Chem Soc 1993; 115:5825-5826.
10. Rinehart KL, Gloer JB, Hughes RG, Renis HE, McGovren JP, Swynenberg EB, et al. Didemnins: antiviral and antitumor depsipeptides from a Caribbean tunicate. Science 1981; 212:933-935.
11. Tran TD, Pham NB, Fechner G, Zencak D, Vu HT, Hooper JN, et al. Cytotoxic cyclic depsipeptides from the Australian marine sponge Neamphius huxleyi. J Nat Prod 2012; 75:2200-2208.
12. Azzi A, Azzone GF. Potassium-transport-linked swelling induced by valinomycin in liver mitochondria. Biochem J 1965; 96:1C-2C.
13. Lam KS, Gustavson DR, Hesler GA, Dabrah TT, Matson JA, Berry RL, et al. Korkormicins, novel depsipeptide antitumor antibiotics from Micromonospora sp C39500: fermentation, precursor directed biosynthesis and biological activities. J Ind Microbiol 1995; 15:60-65.
14. Huang CH, Crooke ST. Effects of structural modifications of antitumor antibiotics (luzopeptins) on the interactions with deoxyribonucleic acid. Cancer Res 1985; 45:3768-3773.
15. Zolova OE, Mady AS, Garneau-Tsodikova S. Recent developments in bisintercalator natural products. Biopolymers 2010; 93:777-790.
16. Ueda H, Nakajima H, Hori Y, Fujita T, Nishimura M, Goto T, et al. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968 I. Taxonomy, fermentation, isolation, physico-chemical and biological properties, and antitumor activity. J Antibiot (Tokyo) 1994; 47:301-310.
17. Schwartz RE, Hirsch CF, Sesin DF, Flor JE, Chartrain M, Fromtling RE, et al. Pharmaceuticals from cultured algae. J Ind Microbiol 1990; 5:113-124.
18. Chen BD, Nakeff A, Valeriote F. Cellular uptake of a novel cytotoxic agent, cryptophycin-52, by human THP-1 leukemia cells and H-125 lung tumor cells. Int J Cancer 1998; 77:869-873.
19. Mackedonski VV. Effect of echinomycin and olivomycin on RNA synthesis in ehrlich ascites tumour cells. FEBS Lett 1969; 5:73-76.
20. Ballard CE, Yu H, Wang B. Recent developments in depsipeptide research. Curr Med Chem 2002; 9:471-498.
21. Lemmens-Gruber R, Kamyar MR, Dornetshuber R. Cyclodepsipeptides-potential drugs and lead compounds in the drug development process. Curr Med Chem 2009; 16:1122-1137.
22. Klein B, Wörndl K, Lütz-Meindl U, Kerschbaum HH. Perturbation of intracellular K(+) homeostasis with valinomycin promotes cell death by mitochondrial swelling and autophagic processes. Apoptosis 2011; 16:1101-1117.
23. Iacobazzi RM, Annese C, Azzariti A, D'Accolti L, Franco M, Fusco C, et al. Antitumor potential of conjugable valinomycins bearing hydroxyl sites: in vitro studies. ACS Med Chem Lett 2013; 4:1189-1192.
24. Kamyar M, Rawnduzi P, Studenik CR, Kouri K, Lemmens-Gruber R. Investigation of the electrophysiological properties of enniatins. Arch Biochem Biophys 2004; 429:215-223.
25. Sy-Cordero AA, Pearce CJ, Oberlies NH. Revisiting the enniatins: a review of their isolation, biosynthesis, structure determination and biological activities. J Antibiot (Tokyo) 2012; 65:541-549.
26. Liu S, Gu W, Lo D, Ujiki M, Adrian TE, Soff GA, et al. N-methylsansalvamide a peptide analogues. Potent new antitumor agents. J Med Chem 2005; 48:3630-3638.
27. Zhang G, Liu S, Liu Y, Wang F, Ren J, Gu J, et al. A novel cyclic pentapeptide, H-10, inhibits B16 cancer cell growth and induces cell apoptosis. Oncol Lett 2014; 8:248-252.
28. Kitagaki J, Yang Y. DNA intercalator korkormicin A preferentially kills tumor cells expressing wild type p53. Biochem Biophys Res Commun 2011; 414:186-191.
29. Dawson S, Malkinson JP, Paumier D, Searcey M. Bisintercalator natural products with potential therapeutic applications: isolation, structure determination, synthetic and biological studies. Nat Prod Rep 2007; 24:109-126.
30. Viehrig K, Surup F, Harmrolfs K, Jansen R, Kunze B, Müller R. Concerted action of P450 plus helper protein to form the amino-hydroxy-piperidone moiety of the potent protease inhibitor crocapeptin. J Am Chem Soc 2013; 135:16885-16894.
31. Kwan JC, Liu Y, Ratnayake R, Hatano R, Kuribara A, Morimoto C, et al. Grassypeptolides as natural inhibitors of dipeptidyl peptidase 8 and T-cell activation. Chembiochem 2014; 15:799-804.
32. Piekarz RL, Robey R, Sandor V, Bakke S, Wilson WH, Dahmoush L, et al. Inhibitor of histone deacetylation, depsipeptide (FR901228), in the treatment of peripheral and cutaneous T-cell lymphoma: a case report. Blood 2001; 98:2865-2868.
33. Piekarz RL, Frye R, Turner M, Wright JJ, Allen SL, Kirschbaum MH, et al. Phase II multi-institutional trial of the histone deacetylase inhibitor romidepsin as monotherapy for patients with cutaneous T-cell lymphoma. J Clin Oncol 2009; 27:5410-5417.
34. Whittaker SJ, Demierre MF, Kim EJ, Rook AH, Lerner A, Duvic M, et al. Final results from a multicenter, international, pivotal study of romidepsin in refractory cutaneous T-cell lymphoma. J Clin Oncol 2010; 28:4485-4491.
35. Ueda H, Manda T, Matsumoto S, Mukumoto S, Nishigaki F, Kawamura I, et al. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. III. Antitumor activities on experimental tumors in mice. J Antibiot (Tokyo) 1994; 47:315-323.
36. Sandor V, Bakke S, Robey RW, Kang MH, Blagosklonny MV, Bender J, et al. Phase I trial of the histone deacetylase inhibitor, depsipeptide (FR901228, NSC 630176), in patients with refractory neoplasms. Clin Cancer Res 2002; 8:718-728.
37. Marshall JL, Rizvi N, Kauh J, Dahut W, Figuera M, Kang MH, et al. A phase I trial of depsipeptide (FR901228) in patients with advanced cancer. J Exp Ther Oncol 2002; 2:325-332.
38. Piekarz RL, Frye R, Prince HM, Kirschbaum MH, Zain J, Allen SL, et al. Phase 2 trial of romidepsin in patients with peripheral T-cell lymphoma. Blood 2011; 117:5827-5834.
39. Mercurio C, Minucci S, Pelicci PG. Histone deacetylases and epigenetic therapies of hematological malignancies. Pharmacol Res 2010; 62:18-34.
40. Stadler WM, Margolin K, Ferber S, McCulloch W, Thompson JA. A phase II study of depsipeptide in refractory metastatic renal cell cancer. Clin Genitourin Cancer 2006; 5:57-60.
41. Whitehead RP, Rankin C, Hoff PM, Gold PJ, Billingsley KG, Chapman RA, et al. Phase II trial of romidepsin (NSC-630176) in previously treated colorectal cancer patients with advanced disease: a Southwest Oncology Group study (S0336). Invest New Drugs 2009; 27:469-475.
42. Schrump DS, Fischette MR, Nguyen DM, Zhao M, Li X, Kunst TF, et al. Clinical and molecular responses in lung cancer patients receiving romidepsin. Clin Cancer Res 2008; 14:188-198.
43. Paoluzzi L, Scotto L, Marchi E, Zain J, Seshan VE, O'Connor OA. Romidepsin and belinostat synergize the antineoplastic effect of bortezomib in mantle cell lymphoma. Clin Cancer Res 2010; 16:554-565.
44. Harrison SJ, Quach H, Link E, Seymour JF, Ritchie DS, Ruell S, et al. A high rate of durable responses with romidepsin, bortezomib, and dexamethasone in relapsed or refractory multiple myeloma. Blood 2011; 118:6274-6283.
45. Bertino EM, Otterson GA. Romidepsin: a novel histone deacetylase inhibitor for cancer. Expert Opin Investig Drugs 2011; 20:1151-1158.
46. Nakajima H, Kim YB, Terano H, Yoshida M, Horinouchi S. FR901228, a potent antitumor antibiotic, is a novel histone deacetylase inhibitor. Exp Cell Res 1998; 241:126-133.
47. Kikuchi J,Wada T, Shimizu R, Izumi T, Akutsu M, Mitsunaga K, et al. Histone deacetylases are critical targets of bortezomib-induced cytotoxicity in multiple myeloma. Blood 2010; 116:406-417.
48. Hoshino I, Matsubara H, Akutsu Y, Nishimori T, Yoneyama Y, Murakami K, et al. Gene expression profiling induced by histone deacetylase inhibitor, FK228, in human esophageal squamous cancer cells. Oncol Rep 2007; 18:585-592.
49. Abbas T, Dutta A. p21 in cancer: intricate networks and multiple activities. Nat Rev Cancer 2009; 9:400-414.
50. Rajgolikar G, Chan KK, Wang HC. Effects of a novel antitumor depsipeptide, FR901228, on human breast cancer cells. Breast Cancer Res Treat 1998; 51:29-38.
51. Sandor V, Senderowicz A, Mertins S, Sackett D, Sausville E, Blagosklonny MV, et al. P21-dependent g(1)arrest with downregulation of cyclin D1 and upregulation of cyclin E by the histone deacetylase inhibitor FR901228. Br J Cancer 2000; 83:817-825.
52. Zhao Y, Lu S, Wu L, Chai G, Wang H, Chen Y, et al. Acetylation of p53 at lysine 373/382 by the histone deacetylase inhibitor depsipeptide induces expression of p21(Waf1/Cip1). Mol Cell Biol 2006; 26:2782-2790.
53. Khan SB, Maududi T, Barton K, Ayers J, Alkan S. Analysis of histone deacetylase inhibitor, depsipeptide (FR901228), effect on multiple myeloma. Br J Haematol 2004; 125:156-161.
54. Yu XD, Wang SY, Chen GA, Hou CM, Zhao M, Hong JA, et al. Apoptosis induced by depsipeptide FK228 coincides with inhibition of survival signaling in lung cancer cells. Cancer J 2007; 13:105-113.
55. Zhang Y, Adachi M, Kawamura R, Imai K. Bmf is a possible mediator in histone deacetylase inhibitors FK228 and CBHA-induced apoptosis. Cell Death Differ 2006; 13:129-140.
56. Zhang Y, Adachi M, Zhao X, Kawamura R, Imai K. Histone deacetylase inhibitors FK228, N-(2-aminophenyl)-4-[N-(pyridin-3-yl-methoxycarbonyl) amino-methyl]benzamide and m-carboxycinnamic acid bis-hydroxamide augment radiation-induced cell death in gastrointestinal adenocarcinoma cells. Int J Cancer 2004; 110:301-308.
57. Cain JM, Liu PY, Alberts DE, Gallion HH, Laufman L, O'Sullivan J, et al. Phase II trial of didemnin-B in advanced epithelial ovarian cancer. A Southwest Oncology Group study. Invest New Drugs 1992; 10:23-24.
58. Taylor SA, Goodman P, Crawford ED, Stuckey WJ, Stephens RL, Gaynor ER. Phase II evaluation of didemnin B in advanced adenocarcinoma of the kidney. A Southwest Oncology Group study. Invest New Drugs 1992; 10:55-56.
59. Benvenuto JA, Newman RA, Bignami GS, Raybould TJ, Raber MN, Esparza L, et al. Phase II clinical and pharmacological study of didemnin B in patients with metastatic breast cancer. Invest New Drugs 1992; 10:113-117.
60. Sondak VK, Kopecky KJ, Liu PY, Fletcher WS, Harvey WH, Laufman LR. Didemnin B in metastatic malignant melanoma: a phase II trial of the Southwest Oncology Group. Anticancer Drugs 1994; 5:147-150.
61. Shin DM, Holoye PY, Forman A, Winn R, Perez-Soler R, Dakhil S, et al. Phase II clinical trial of didemnin B in previously treated small cell lung cancer. Invest New Drugs 1994; 12:243-249.
62. Weiss RB, Peterson BL, Allen SL, Browning SM, Duggan DB, Schiffer CA. A phase II trial of didemnin B in myeloma. A Cancer and Leukemia Group B (CALGB) study. Invest New Drugs 1994; 12:41-43.
63. Williamson SK, Wolf MK, Eisenberger MA, O'Rourke M, Brannon W, Crawford ED. Phase II evaluation of didemnin B in hormonally refractory metastatic prostate cancer. A Southwest Oncology Group study. Invest New Drugs 1995; 13:167-170.
64. Goss G, Muldal A, Lohmann R, Taylor M, Lopez P, Armitage G, et al. Didemnin B in favourable histology non-Hodgkin's lymphoma. A phase II study of the National Cancer Institute of Canada Clinical Trials Group. Invest New Drugs 1995; 13:257-260.
65. Mateos MV, Cibeira MT, Richardson PG, Prosper F, Oriol A, de la Rubia J, et al. Phase II clinical and pharmacokinetic study of plitidepsin 3-hour infusion every two weeks alone or with dexamethasone in relapsed and refractory multiple myeloma. Clin Cancer Res 2010; 16:3260-3269.
66. Depenbrock H, Peter R, Faircloth GT, Manzanares I, Jimeno J, Hanauske AR. In vitro activity of aplidine, a new marine-derived anti-cancer compound, on freshly explanted clonogenic human tumour cells and haematopoietic precursor cells. Br J Cancer 1998; 78:739-744.
67. Sakai R, Rinehart KL, Kishore V, Kundu B, Faircloth G, Gloer JB, et al. Structure-activity relationships of the didemnins. J Med Chem 1996; 39:2819-2834.
68. Lobo C, Garciá-Pozo SG, Núñez de Castro I, Alonso FJ. Effect of dehydrodidemnin B on human colon carcinoma cell lines. Anticancer Res 1997; 17:333-336.
69. Gómez SG, Faircloth G, López-Lázaro L, Jimeno J, Bueren JA, Albella B. In vitro hematotoxicity of Aplidine on human bone marrow and cord blood progenitor cells. Toxicol In Vitro 2001; 15:347-350.
70. Straight AM, Oakley K, Moores R, Bauer AJ, Patel A, Tuttle RM, et al. Aplidin reduces growth of anaplastic thyroid cancer xenografts and the expression of several angiogenic genes. Cancer Chemother Pharmacol 2006; 57:7-14.
71. Caers J, Menu E, De Raeve H, Lepage D, Van Valckenborgh E, Van Camp B, et al. Antitumour and antiangiogenic effects of Aplidin in the 5TMM syngeneic models of multiple myeloma. Br J Cancer 2008; 98:1966-1974.
72. Maroun JA, Belanger K, Seymour L, Matthews S, Roach J, Dionne J, et al. Phase I study of aplidine in a dailyx5 one-hour infusion every 3 weeks in patients with solid tumors refractory to standard therapy. A National Cancer Institute of Canada Clinical Trials Group study: NCIC CTG IND 115. Ann Oncol 2006; 17:1371-1378.
73. Izquierdo MA, Bowman A, Garciá M, Jodrell D, Martinez M, Pardo B, et al. Phase I clinical and pharmacokinetic study of plitidepsin as a 1-hour weekly intravenous infusion in patients with advanced solid tumors. Clin Cancer Res 2008; 14:3105-3112.
74. Faivre S, Chièze S, Delbaldo C, Ady-Vago N, Guzman C, Lopez-Lazaro L, et al. Phase I and pharmacokinetic study of aplidine, a new marine cyclodepsipeptide in patients with advanced malignancies. J Clin Oncol 2005; 23:7871-7880.
75. Geoerger B, Estlin EJ, Aerts I, Kearns P, Gibson B, Corradini N, et al. A phase I and pharmacokinetic study of plitidepsin in children with advanced solid tumours: an Innovative Therapies for Children with Cancer (ITCC) study. Eur J Cancer 2012; 48:289-296.
76. Eisen T, Thomas J, Miller WH, Gore M, Wolter P, Kavan P, et al. Phase II study of biweekly plitidepsin as second-line therapy in patients with advanced malignant melanoma. Melanoma Res 2009; 19:185-192.
77. Baudin E, Droz JP, Paz-Ares L, van Oosterom AT, Cullell-Young M, Schlumberger M. Phase II study of plitidepsin 3-hour infusion every 2 weeks in patients with unresectable advanced medullary thyroid carcinoma. Am J Clin Oncol 2010; 33:83-88.
78. Schöffski P, Guillem V, Garcia M, Rivera F, Tabernero J, Cullell M, et al. Phase II randomized study of Plitidepsin (Aplidin), alone or in association with L-carnitine, in patients with unresectable advanced renal cell carcinoma. Mar Drugs 2009; 7:57-70.
79. Eisen T, Thatcher N, Leyvraz S, Miller WH, Couture F, Lorigan P, et al. Phase II study of weekly plitidepsin as second-line therapy for small cell lung cancer. Lung Cancer 2009; 64:60-65.
80. Ribrag V, Caballero D, Fermé C, Zucca E, Arranz R, Briones J, et al. Multicenter phase II study of plitidepsin in patients with relapsed/refractory non-Hodgkin's lymphoma. Haematologica 2013; 98:357-363.
81. Garciá-Fernández LF, Losada A, Alcaide V, Alvarez AM, Cuadrado A, González L, et al. Aplidin induces the mitochondrial apoptotic pathway via oxidative stress-mediated JNK and p38 activation and protein kinase C delta. Oncogene 2002; 21:7533-7544.
82. Cuadrado A, Garcia-Fernandez LF, Gonzalez L, Suarez Y, Losada A, Alcaide V, et al. Aplidin induces apoptosis in human cancer cells via glutathione depletion and sustained activation of the epidermal growth factor receptor, Src, JNK, and p38 MAPK. J Biol Chem 2003; 278:241-250.
83. Cuadrado A, González L, Suárez Y, Martínez T, Munõz A. JNK activation is critical for aplidin-induced apoptosis. Oncogene 2004; 23:4673-4680.
84. González-Santiago L, Suárez Y, Zarich N, Munõz-Alonso MJ, Cuadrado A, Martínez T, et al. Aplidin induces JNK-dependent apoptosis in human breast cancer cells via alteration of glutathione homeostasis, Rac1 GTPase activation, and MKP-1 phosphatase downregulation. Cell Death Differ 2006; 13:1968-1981.
85. Erba E, Bassano L, Di Liberti G, Muradore I, Chiorino G, Ubezio P, et al. Cell cycle phase perturbations and apoptosis in tumour cells induced by aplidine. Br J Cancer 2002; 86:1510-1517.
86. Erba E, Serafini M, Gaipa G, Tognon G, Marchini S, Celli N, et al. Effect of aplidin in acute lymphoblastic leukaemia cells. Br J Cancer 2003; 89:763-773.
87. Biscardi M, Caporale R, Balestri F, Gavazzi S, Jimeno J, Grossi A. VEGF inhibition and cytotoxic effect of aplidin in leukemia cell lines and cells from acute myeloid leukemia. Ann Oncol 2005; 16:1667-1674.
88. Munõz-Alonso MJ, González-Santiago L, Zarich N, Martínez T, Alvarez E, Rojas JM, et al. Plitidepsin has a dual effect inhibiting cell cycle and inducing apoptosis via Rac1/c-Jun NH2-terminal kinase activation in human melanoma cells. J Pharmacol Exp Ther 2008; 324:1093-1101.
89. Broggini M, Marchini SV, Galliera E, Borsotti P, Taraboletti G, Erba E, et al. Aplidine, a new anticancer agent of marine origin, inhibits vascular endothelial growth factor (VEGF) secretion and blocks VEGF-VEGFR-1 (flt-1) autocrine loop in human leukemia cells MOLT-4. Leukemia 2003; 17:52-59.
90. Gao J, Hamann MT. Chemistry and biology of kahalalides. Chem Rev 2011; 111:3208-3235.
91. Shilabin AG, Kasanah N, Wedge DE, Hamann MT. Lysosome and HER3 (ErbB3) selective anticancer agent kahalalide F: semisynthetic modifications and antifungal lead-exploration studies. J Med Chem 2007; 50:4340-4350.
92. Faircloth G, Cuevas C. Kahalalide F and ES285: potent anticancer agents from marine molluscs. Prog Mol Subcell Biol 2006; 43:363-379.
93. Bonnard I, Manzanares I, Rinehart KL. Stereochemistry of kahalalide F. J Nat Prod 2003; 66:1466-1470.
94. Rademaker-Lakhai JM, Horenblas S, Meinhardt W, Stokvis E, de Reijke TM, Jimeno JM, et al. Phase I clinical and pharmacokinetic study of kahalalide F in patients with advanced androgen refractory prostate cancer. Clin Cancer Res 2005; 11:1854-1862.
95. Pardo B, Paz-Ares L, Tabernero J, Ciruelos E, Garciá M, Salazar R, et al. Phase I clinical and pharmacokinetic study of kahalalide F administered weekly as a 1-hour infusion to patients with advanced solid tumors. Clin Cancer Res 2008; 14:1116-1123.
96. Salazar R, Cortés-Funes H, Casado E, Pardo B, López-Martín A, Cuadra C, et al. Phase I study of weekly kahalalide F as prolonged infusion in patients with advanced solid tumors. Cancer Chemother Pharmacol 2013; 72:75-83.
97. Martín-Algarra S, Espinosa E, Rubió J, López López JJ, Manzano JL, Carrión LA, et al. Phase II study of weekly Kahalalide F in patients with advanced malignant melanoma. Eur J Cancer 2009; 45:732-735.
98. Garciá-Rocha M, Bonay P, Avila J. The antitumoral compound Kahalalide F acts on cell lysosomes. Cancer Lett 1996; 99:43-50.
99. Janmaat ML, Rodriguez JA, Jimeno J, Kruyt FA, Giaccone G. Kahalalide F induces necrosis-like cell death that involves depletion of ErbB3 and inhibition of Akt signaling. Mol Pharmacol 2005; 68:502-510.
100. Provencio M, Sánchez A, Gasent J, Gómez P, Rosell R. Cancer treatments: can we find treasures at the bottom of the sea? Clin Lung Cancer 2009; 10:295-300.
101. Salazar R, Jones RJ, Oaknin A, Crawford D, Cuadra C, Hopkins C, et al. A phase I and pharmacokinetic study of elisidepsin (PM02734) in patients with advanced solid tumors. Cancer Chemother Pharmacol 2012; 70:673-681.
102. Molina-Guijarro JM, Maciás Á, Garciá C, Munõz E, Garciá-Fernández LF, David M, et al. Irvalec inserts into the plasma membrane causing rapid loss of integrity and necrotic cell death in tumor cells. PLoS One 2011; 6: e19042.
103. Ling YH, Aracil M, Jimeno J, Perez-Soler R, Zou Y. Molecular pharmacodynamics of PM02734 (elisidepsin) as single agent and in combination with erlotinib; synergistic activity in human non-small cell lung cancer cell lines and xenograft models. Eur J Cancer 2009; 45:1855-1864.
104. Ling YH, Aracil M, Zou Y, Yuan Z, Lu B, Jimeno J, et al. PM02734 (elisidepsin) induces caspase-independent cell death associated with features of autophagy, inhibition of the Akt/mTOR signaling pathway, and activation of death-associated protein kinase. Clin Cancer Res 2011; 17:5353-5366.
105. Váradi T, Roszik J, Lisboa D, Vereb G, Molina-Guijarro JM, Galmarini CM, et al. ErbB protein modifications are secondary to severe cell membrane alterations induced by elisidepsin treatment. Eur J Pharmacol 2011; 667:91-99.
106. Herrero AB, Astudillo AM, Balboa MA, Cuevas C, Balsinde J, Moreno S. Levels of SCS7/FA2H-mediated fatty acid 2-hydroxylation determine the sensitivity of cells to antitumor PM02734. Cancer Res 2008; 68:9779-9787.
107. Barrow RA, Hemscheidt T, Liang J, Paik S, Moore RE, Tius MA. Total Synthesis of cryptophycins. Revision of the structures of cryptophycins A and C. J Am Chem Soc 1995; 117:2479-2490.
108. Smith CD, Zhang X, Mooberry SL, Patterson GM, Moore RE. Cryptophycin: a new antimicrotubule agent active against drugresistant cells. Cancer Res 1994; 54:3779-3784.
109. Trimurtulu G, Ohtani I, Patterson GML, Moore RE, Corbett TH, Valeriote FA, et al. Total structures of cryptophycins, potent antitumor depsipeptides from the blue-green alga Nostoc sp. Strain GSV 224t. J Am Chem Soc 1994; 116:4729-4737.
110. Corbett TH, Valeriote FA, Demchik L, Lowichik N, Polin L, Panchapor C, et al. Discovery of cryptophycin-1 and BCN-183577: examples of strategies and problems in the detection of antitumor activity in mice. Invest New Drugs 1997; 15:207-218.
111. Liang J, Moore RE, Moher ED, Munroe JE, Al-awar RS, Hay D, et al. Cryptophycins-309, 249 and other cryptophycin analogs: preclinical efficacy studies with mouse and human tumors. Invest New Drugs 2005; 23:213-224.
112. Kobayashi M, Wang W, Ohyabu N, Kurosu M, Kitagawa I. Improved total synthesis and structure-activity relationship of arenastatin A, a potent cytotoxic spongean depsipeptide. Chem Pharm Bull (Tokyo) 1995; 43:1598-1600.
113. Andavan GS, Lemmens-Gruber R. Cyclodepsipeptides from marine sponges: natural agents for drug research. Mar Drugs 2010; 8:810-834.
114. Patel VF, Andis SL, Kennedy JH, Ray JE, Schultz RM. Novel cryptophycin antitumor agents: synthesis and cytotoxicity of fragment "B" analogues. J Med Chem 1999; 42:2588-2603.
115. Wagner MM, Paul DC, Shih C, Jordan MA, Wilson L, Williams DC. In vitro pharmacology of cryptophycin 52 (LY355703) in human tumor cell lines. Cancer Chemother Pharmacol 1999; 43:115-125.
116. Stevenson JP, Sun W, Gallagher M, Johnson R, Vaughn D, Schuchter L, et al. Phase I trial of the cryptophycin analogue LY355703 administered as an intravenous infusion on a day 1 and 8 schedule every 21 days. Clin Cancer Res 2002; 8:2524-2529.
117. Sessa C, Weigang-Köhler K, Pagani O, Greim G, Mora O, De Pas T, et al. Phase I and pharmacological studies of the cryptophycin analogue LY355703 administered on a single intermittent or weekly schedule. Eur J Cancer 2002; 38:2388-2396.
118. Edelman MJ, Gandara DR, Hausner P, Israel V, Thornton D, DeSanto J, et al. Phase 2 study of cryptophycin 52 (LY355703) in patients previously treated with platinum based chemotherapy for advanced non-small cell lung cancer. Lung Cancer 2003; 39:197-199.
119. D'Agostino G, del Campo J, Mellado B, Izquierdo MA, Minarik T, Cirri L, et al. A multicenter phase II study of the cryptophycin analog LY355703 in patients with platinum-resistant ovarian cancer. Int J Gynecol Cancer 2006; 16:71-76.
120. Bai R, Schwartz RE, Kepler JA, Pettit GR, Hamel E. Characterization of the interaction of cryptophycin 1 with tubulin: binding in the Vinca domain, competitive inhibition of dolastatin 10 binding, and an unusual aggregation reaction. Cancer Res 1996; 56:4398-4406.
121. Smith CD, Zhang X. Mechanism of action cryptophycin. Interaction with the Vinca alkaloid domain of tubulin. J Biol Chem 1996; 271:6192-6198.
122. Lu K, Dempsey J, Schultz RM, Teicher BA. Cryptophycin-induced hyperphosphorylation of Bcl-2, cell cycle arrest and growth inhibition in human H460 NSCLC cells. Cancer Chemother Pharmacol 2001; 47:170-178.
123. Panda D, DeLuca K, Williams D, Jordan MA, Wilson L. Antiproliferative mechanism of action of cryptophycin-52: kinetic stabilization of microtubule dynamics by high-affinity binding to microtubule ends. Proc Natl Acad Sci USA 1998; 95:9313-9318.
124. Shih C, Teicher BA. Cryptophycins: a novel class of potent antimitotic antitumor depsipeptides. Curr Pharm Des 2001; 7: 1259-1276.
125. Kessel D, Luo Y. Cells in cryptophycin-induced cell-cycle arrest are susceptible to apoptosis. Cancer Lett 2000; 151:25-29.
126. Subramanian B, Nakeff A, Media JE,Wiegand RA, Valeriote FA. Inhibition of macromolecular synthesis by cryptophycin-52. Anticancer Drugs 2002; 13:1061-1068.
127. Newman DJ, Cragg GM. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod 2012; 75:311-335.