Quinones and halogenated monoterpenes of algal origin show anti-proliferative effects against breast cancer cells in vitro

Investigational New Drugs

Volumn 30, Issue 6, 2012, Pages 2187-2200

  De La Mare, Jo Anne ^a   Lawson, Jessica C ^a   Chiwakata, Maynard T ^a   Beukes, Denzil R ^a   Edkins, Adrienne L ^a   Blatch, Gregory L ^a,b  

^a RHODES UNIVERSITY   (South Africa)

^b VICTORIA UNIVERSITY   (Australia)

Author keywords

Apoptosis; Breast cancer; Halogens; Marine natural products; Quinones

Indexed keywords

CASPASE 13; CASPASE 3; CASPASE 6; CASPASE 8; CASPASE 9; HMR 3004; PROTEIN BCL 2; QUINONE DERIVATIVE; RU 002; RU 007; RU 008; RU 015; RU 016; RU 019; RU 048; RU 050; RU 054; SARGAQUINOIC ACID; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ALGA; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; ASSAY; BREAST CANCER; CANCER CELL; CELL DEATH; CONFOCAL MICROSCOPY; CONTROLLED STUDY; DOWN REGULATION; DRUG CYTOTOXICITY; FLOW CYTOMETRY; G1 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; INFLAMMATION; METASTASIS; PARP CLEAVAGE ASSAY; PRIORITY JOURNAL;

ALKENES; ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; BENZOQUINONES; BREAST NEOPLASMS; CASPASES; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; FEMALE; HUMANS; MONOTERPENES; PLOCAMIUM; PROTO-ONCOGENE PROTEINS C-BCL-2; REACTIVE OXYGEN SPECIES; SARGASSUM;

EID: 84875489121     PISSN: 01676997     EISSN: 15730646     Source Type: Journal    
DOI: 10.1007/s10637-011-9788-0     Document Type: Article

References (42)

1. World Health Statistics (2008) Part 1: ten highlights in health statistics, breast cancer: mortality and screening. World Health Organisation, Geneva, pp 21-23
2. Peto R, Boreham J, Clarke M, Davies C, Beral V (2000) UK and USA breast cancer deaths down 25% in year 2000 at ages 20-69 years. Lancet 355:1822-1822
3. Howe HL, Wingo PA, Thun MJ, Ries LA, Rosenberg HM, Feigal EG, Edwards BK (2001) Annual report to the nation on the status of cancer (1973 through 1998), featuring cancers with recent increasing trends. J Natl Cancer Inst 93:824-842
4. Zhou J, Zhang H, Gu P, Bai J, Margolick M, Zhang Y (2008) NF-κB pathway inhibitors preferentially inhibit breast cancer stem-like cells. Breast Canc Res Treat 111:419-427
5. Jin Z, El-Deiry WS (2005) Overview of cell death signaling pathways. Canc Biol Ther 4(2):139-163
6. Iannolo G, Conticello C, Memeo L, De Maria R (2008) Apoptosis in normal and cancer cells. Crit Rev Oncol Hematol 66:42-51
7. Fink SL, Cookson BT (2005) Apoptosis, pyroptosis, and necrosis: mechanistic description of dead and dying eukaryotic cells. Infect Immun 73:1907-1916
8. Klener P Jr, Andera L, Klener P, Necas E, Zivny J (2006) Cell death signalling pathways in the pathogenesis and therapy of haematologic malignancies: overview of apoptotic pathways. J Folia Biol (Praha) 52:34-44
9. Leist M, Jaattela M (2001) Four deaths and a funeral: from cas-pases to alternative mechanisms. Nat Rev Mol Cell Biol 2:589-98
10. Nagata S (1997) Apoptosis by death factor. Cell 88:355-365
11. Kroemer G, Reed JC (2000) Mitochondrial control of cell death. Nat Med 6:513-519
12. Kerr JF, Wyllie AH, Currie AR (1972) Apoptosis: a basic biological phenomenon with wide-ranging implications in tissue kinetics. Br J Cancer 26:239-57
13. Debatin K-M, Krammer PH (2004) Death receptors in chemotherapy and cancer. Oncogene 23:2950-2966
14. Boulares AH, Yakovlev AG, Ivanova V, Stoica BA, Wang G, Iyer S, Smulson M (1999) Role of poly(ADP-ribose) polymerase (PARP) cleavage in apoptosis. Caspase 3-resistant PARP mutant increases rates of apoptosis in transfected cells. J Biol Chem 274:22932-22940
15. Carté BK (1996) Biomedical potential of marine natural products. Bioscience 46(4):271-286
16. Jha RK, Zi-rong X (2004) Biomedical compounds from marine organisms. Mar Drugs 2:123-146
17. König GM, Wright AD, Franzblau SG (2000) Assessment of antimycobacterial activity of a series of mainly marine derived natural products. Planta Medica 66:337-342
18. Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2003) Marine natural products. Nat Prod Rep 20:1-48
19. Knott MG, Mkwananzi HB, Arendse CE, Hendricks DT, Bolton JJ, Beukes DR (2005) Plocoralides A-C, polyhalogenated mono-terpenes from the marine alga Plocamium corallorhiza. Phyto-chem 66:1108-1112
20. Fuller RW, Cardellina JH II, Kato Y, Brinen LS, Clardy J, Snader KM, Boyd MR (1992) A pentahalogenated monoterpene from the red alga Portieria hornemannii produces a novel cytotoxicity profile against a diverse panel of human tumor cell lines. J Med Chem 35:3007-3011
21. Mann MGA, Mkwananzi HB, Antunes EM, Whibley CE, Hendricks DT, Bolton JJ, Beukes DR (2007) Halogenated monoterpene aldehydes from the South African marine alga Plocomium corallorhiza. J Nat Prod 70:596-599
22. Afolayan AF, Bolton JJ, Lategan CA, Smith PJ, Beukes DR (2008) Fucoxanthin, tetraprenylated toluquinone and toluhydroquinone metabolites from Sargassum heterophyllum inhibit the in vitro growth of the malaria parasite Plasmodium falciparum. Z Natur-forsch 63c:848-852
23. Hur S, Lee H, Kim Y, Lee B-H, Shin J, Kim TY (2008) Sargaqui-noic acid and sargachromenal, extracts of Sargassum sagamianum induce apoptosis in HaCaT cells and mice skin: Its potentiation of UVB-induced apoptosis. Eur J Pharmacol 582:1-11
24. Warleta F, Campos M, Allouche Y, Sanchez-Quesada C, Ruiz-Mora J, Beltran G, Gaforio JJ (2010) Squalene protects against oxidative DNA damage in MCF10A human mammary epithelial cells but not in MCF-7 and MDA-MB-231 human breast cancer cells. Food Chem Toxicol 48:1092-1100
25. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46:3-26
26. Chiosis G (2003) Targeting chaperones in transformed systems-a focus on Hsp90 and cancer. Expert Opin Ther Targets 10:37-50
27. Chaitanya GV, Babu PP (2009) Differential PARP cleavage: an indication of heterogeneous forms of cell death and involvement of multiple proteases in the infarct of focal cerebral ischemia in rat. Cell Mol Neurobiol 29:563-573
28. Tzu-Hao W, Hsin-Shih W, Yung-Kwei S (2000) Paclitaxel induced cell death. Cancer 88:2619-2628
29. Choi BW, Park SH, Kim ES, Shin J, Roh SS, Shin HC, Lee BH (2007) Anticholinesterase activity of plastoquinones from Sargas-sum sagamianum: lead compounds for Alzheimer's disease therapy. Phytother Res 21:423-426
30. Hosokawa M, Wanezaki S, Miyauchi K, Kurihara H, Kohno H, Kawabata J, Odashima S, Takahashi K (1999) Apoptosis-inducing effect of fucoxanthin on human leukemia cell line HL-60. Food Sci Technol Res 5(3):243-246
31. Carr C, Ng J, Wigmore T (2008) The side effects of chemothera-peutic agents. Cur Anaes Crit Care 19:70-79
32. Dwight ES, Lawrence WD, Carl C, Nanci LW, Hangming R, Gunter D (1997) Paclitaxel-induced apoptosis in MCF-7 breast-cancer cells. Int J Cancer 70:214-220
33. Bachur NR, Gordon SL, Gee MV (1978) A general mechanism for microsomal activation of quinone anticancer agents to free radicals. Cancer Res 38:1745-1750
34. Hoyt MT, Palchaudhuri R, Hergenrother PJ (2011) Cribrostatin 6 induces death in cancer cells through a reactive oxygen species (ROS)-mediated mechanism. Investig New Drugs 29:562-573
35. Bertram S (2000) The molecular biology of cancer. Mol Asp Med 21:167-223
36. Johnstone RW, Ruefli AA, Lowe SW (2002) Apoptosis: a link between cancer genetics and chemotherapy. Cell 108:153-164
37. Shao Y, Gao Z, Marks PA, Jiang X (2004) Apoptotic and auto-phagic cell death induced by histone deacetylase inhibitors. Proc Natl Acad Sci USA 101:18030-18035
38. Kamei Y, Tsang CK (2003) Sargaquinoic acid promotes neu-rite outgrowth via protein kinase A and MAP kinases-mediated signaling pathways in PC12D cells. Int J Dev Neurosci 21:255-262
39. Dive C, Gregory CD, Phipps DJ, Evans DL, Milner AE, Wyllie AH (1992) Analysis and discrimination of necrosis and apoptosis (programmed cell death) by multiparameter flow cytometry. Biochim Biophys Acta 1133:275-285
40. Soldani C, Scovassi AI (2002) Poly(ADP-ribose) polymerase-1 cleavage during apoptosis: an update. Apoptosis 7:321-328
41. Jacobson MD, Raff MC (1994) Programmed cell death and Bcl-2 protection in very low oxygen. Nature 374:814-816
42. de Ines C, Argandona VH, Rovirosa J, San-Martin A, Diaz-Marrero AR, Cueto M, Gonzalez-Coloma A (2004) Cytotoxic activity of halogenated monoterpenes from Plocamium cartilagi-neum. Z Naturforsch 59:339-344