Anticolon cancer activity of largazole, a marine-derived tunable histone deacetylase inhibitor

Journal of Pharmacology and Experimental Therapeutics

Volumn 335, Issue 2, 2010, Pages 351-361

  Liu, Yanxia ^a   Salvador, Lilibeth A ^a   Byeon, Seongrim ^b   Ying, Yongcheng ^b   Kwan, Jason C ^a   Law, Brian K ^a   Hong, Jiyong ^b   Luesch, Hendrik ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; HISTONE DEACETYLASE; HISTONE DEACETYLASE INHIBITOR; LARGAZOLE; ROMIDEPSIN; UNCLASSIFIED DRUG; VORINOSTAT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER INHIBITION; CELL CYCLE ARREST; COLON CANCER; CONCENTRATION RESPONSE; ENZYME INHIBITION; FEMALE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR DOCKING; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CELL LINE, TUMOR; CELL SURVIVAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLONIC NEOPLASMS; DEPSIPEPTIDES; DOWN-REGULATION; DRUG STABILITY; FEMALE; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENE EXPRESSION REGULATION, NEOPLASTIC; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HUMANS; IMMUNOHISTOCHEMISTRY; MASS SPECTROMETRY; MICE; MICE, NUDE; MOLECULAR STRUCTURE; OLIGONUCLEOTIDE ARRAY SEQUENCE ANALYSIS; RECOMBINANT PROTEINS; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; THIAZOLES; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 78149267515     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.110.172387     Document Type: Article

References (40)

1. Ackley DC, Rockich KT, and Baker TR (2004) Metabolic stability assessed by liver microsomes and hepatocytes, in Optimization in Drug Discovery: In Vitro Methods (Series: Methods in Pharmacology and Toxicology) (eds Yan Z, Caldwell JW) pp 151-162, Springer, New Jersey.
2. Baselga J (2006) Targeting tyrosine kinases in cancer: the second wave. Science 312:1175-1178.
3. Baserga R (2009) The insulin receptor substrate-1: a biomarker for cancer? Exp Cell Res 315:727-732.
4. Benjamini Y and Hochberg Y (1995) Controlling the false discovery rate: a practical and powerful approach to multiple testing. J R Stat Soc B 57:289-300.
5. Bolstad BM, Irizarry RA, Astrand M, and Speed TP (2003) A comparison of normalization methods for high density oligonucleotide array data based on variance and bias. Bioinformatics 19:185-193.
6. Casali PG, Sanfilippo R, and D'Incalci M (2010) Trabectedin therapy for sarcomas. Curr Opin Oncol 22:342-346.
7. Chen CS, Weng SC, Tseng PH, Lin HP, and Chen CS (2005) Histone acetylation-independent effect of histone deacetylase inhibitors on Akt through reshuffling of protein phosphatase 1 complexes. J Biol Chem 280:38879-38887.
8. Chen X, Gardner ER, and Figg WD (2008) Determination of the cyclic depsipeptide FK228 in human and mouse plasma by liquid chromatography with mass spectrometric determination. J Chromatogr B Analyt Technol Biomed Life Sci 865: 153-158.
9. Dokmanovic M, Clarke C, and Marks PA (2007) Histone deacetylase inhibitors: overview and perspectives. Mol Cancer Res 5:981-989. (Pubitemid 350080267)
10. Fenical W, Jensen PR, Palladino MA, Lam KS, Lloyd GK, and Potts BC (2009) Discovery and development of the anticancer agent salinosporamide A (NPI-0052). Bioorg Med Chem 17:2175-2180.
11. Furumai R, Matsuyama A, Kobashi N, Lee KH, Nishiyama M, Nakajima H, Tanaka A, Komatsu Y, Nishino N, Yoshida M, et al. (2002) FK228 (depsipeptide) as a natural prodrug that inhibits class I histone deacetylases. Cancer Res 62:4916-4921.
12. Gentleman RC, Carey VJ, Bates DM, Bolstad B, Dettling M, Dudoit S, Ellis B, Gautier L, Ge Y, Gentry J, et al. (2004) Bioconductor: open software development for computational biology and bioinformatics. Genome Biol 5:R80.
13. Ishihama K, Yamakawa M, Semba S, Takeda H, Kawata S, Kimura S, and Kimura W (2007) Expression of HDAC1 and CBP/p300 in human colorectal carcinomas. J Clin Pathol 60:1205-1210.
14. Kling J (2006) Bundling next-generation cancer therapies for synergy. Nat Biotechnol 24:871-872.
15. Lansigan F and Foss FM (2010) Current and emerging treatment strategies for cutaneous T-cell lymphoma. Drugs 70:273-286.
16. Marks PA and Breslow R (2007) Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug. Nat Biotechnol 25: 84-90.
17. Mayer AM, Glaser KB, Cuevas C, Jacobs RS, Kem W, Little RD, McIntosh JM, Newman DJ, Potts BC, and Shuster DE (2010) The odyssey of marine pharmaceuticals: a current pipeline perspective. Trends Pharmacol Sci 31:255-265.
18. Nakao Y, Narazaki G, Hoshino T, Maeda S, Yoshida M, Maejima H, and Yamashita JK (2008) Evaluation of antiangiogenic activity of azumamides by the in vitro vascular organization model using mouse induced pluripotent stem (iPS) cells. Bioorg Med Chem Lett 18:2982-2984.
19. Nakao Y, Yoshida S, Matsunaga S, Shindoh N, Terada Y, Nagai K, Yamashita JK, Ganesan A, van Soest RW, and Fusetani N (2006) Azumamides A-E, histone deacetylase inhibitory cyclic tetrapeptides from the marine sponge Mycale izuensis. Angew Chem Int Ed 45:7553-7557.
20. Newkirk TL, Bowers AA, and Williams RM (2009) Discovery, biological activity, synthesis and potential therapeutic utility of naturally occurring histone deacetylase inhibitors. Nat Prod Rep 26:1293-1320.
21. Newman DJ and Cragg GM (2007) Natural products as sources of new drugs over the last 25 years. J Nat Prod 70:461-477.
22. Paris M, Porcelloni M, Binaschi M, and Fattori D (2008) Histone deacetylase inhibitors: from bench to clinic. J Med Chem 51:1505-1529.
23. Paull KD, Hamel E, and Malspeis L (1995) Prediction of biochemical mechanism of action from the in vitro antitumor screen of the National Cancer Institute, in Cancer Chemotherapeutic Agents (ed Foye WO) pp 9-45, American Chemical Society Books, Washington, DC.
24. Piña IC, Gautschi JT, Wang GY, Sanders ML, Schmitz FJ, France D, Cornell- Kennon S, Sambucetti LC, Remiszewski SW, Perez LB, et al. (2003) Psammaplins from the sponge Pseudoceratina purpurea: inhibition of both histone deacetylase and DNA methyltransferase. J Org Chem 68:3866-3873.
25. Seiser T, Kamena F, and Cramer N (2008) Synthesis and biological activity of largazole and derivatives. Angew Chem Int Ed Engl 47:6483-6485.
26. Senese S, Zaragoza K, Minardi S, Muradore I, Ronzoni S, Passafaro A, Bernard L, Draetta GF, Alcalay M, Seiser C, et al. (2007) Role for histone deacetylase 1 in human tumor cell proliferation. Mol Cell Biol 27:4784-4795.
27. Shi B, Sepp-Lorenzino L, Prisco M, Linsley P, deAngelis T, and Baserga R (2007) Micro RNA 145 targets the insulin receptor substrate-1 and inhibits the growth of colon cancer cells. J Biol Chem 282:32582-32590.
28. Smyth GK (2004) Linear models and empirical bayes methods for assessing differential expression in microarray experiments. Stat Appl Genet Mol Biol 3:Article3.
29. Spurling CC, Godman CA, Noonan EJ, Rasmussen TP, Rosenberg DW, and Giardina C (2008) HDAC3 overexpression and colon cancer cell proliferation and differentiation. Mol Carcinog 47:137-147.
30. Sun H and Baserga R (2008) The role of insulin receptor substrate-1 in transformation by v-src. J Cell Phys 215:725-732.
31. Taori K, Paul VJ, and Luesch H (2008) Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp. J Am Chem Soc 130:1806-1807.
32. Tashiro E, Tsuchiya A, and Imoto M (2007) Functions of cyclin D1 as an oncogene and regulation of cyclin D1 expression. Cancer Sci 98:629-635.
33. Trott O and Olson AJ (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 31:455-461.
34. Wang DF, Helquist P, Wiech NL, and Wiest O (2005) Toward selective histone deacetylase inhibitor design: homology modeling, docking studies, and molecular dynamics simulations of human class I histone deacetylases. J Med Chem 48: 6936-6947.
35. Wen S, Packham G, and Ganesan A (2008) Macrolactamization versus macrolactonization: total synthesis of FK228, the depsipeptide histone deacetylase inhibitor. J Org Chem 73:9353-9361.
36. Wilson AJ, Byun DS, Popova N, Murray LB, L'Italien K, Sowa Y, Arango D, Velcich A, Augenlicht LH, and Mariadason JM (2006) Histone deacetylase 3 (HDAC3) and other class I HDACs regulate colon cell maturation and p21 expression and are deregulated in human colon cancer. J Biol Chem 281:13548-13558.
37. Ying Y, Liu Y, Byeon SR, Kim H, Luesch H, and Hong J (2008a) Synthesis and activity of largazole analogues with linker and macrocycle modification. Org Lett 10:4021-4024.
38. Ying Y, Taori K, Kim H, Hong J, and Luesch H (2008b) Total synthesis andmolecular target of largazole, a histone deacetylase inhibitor. J Am Chem Soc 130:8455-8459.
39. Yurek-George A, Cecil AR, Mo AH, Wen S, Rogers H, Habens F, Maeda S, Yoshida M, Packham G, and Ganesan A (2007) The first biologically active synthetic analogues of FK228, the depsipeptide histone deacetylase inhibitor. J Med Chem 50:5720-5726.
40. Zeng X, Yin B, Hu Z, Liao C, Liu J, Li S, Li Z, Nicklaus MC, Zhou G, and Jiang S (2010) Total synthesis and biological evaluation of largazole and derivatives with promising selectivity for cancers cells. Org Lett 12:1368-1371.