Macrocyclic histone deacetylase inhibitors

Current Topics in Medicinal Chemistry

Volumn 10, Issue 14, 2010, Pages 1423-1440

  Mwakwari, Sandra C ^a   Patil, Vishal ^a   Guerrant, William ^a   Oyelere, Adegboyega K ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Cyclic tetrapeptide; Depsipeptide; HDAC; Histone deacetylase; Inhibitors; Ketolide; Macrocycles; Macrolide; Peptide mimetic

Indexed keywords

ANTIPARASITIC AGENT; APICIDIN; APICIDIN A; APICIDIN C; APICIDIN D1; APICIDIN D2; AZUMAMIDE A; AZUMAMIDE B; AZUMAMIDE C; AZUMAMIDE D; AZUMAMIDE E; BENZAMIDE DERIVATIVE; CHAP 31; CHLAMYDOCIN; CYCLO[LEUCYLPIPECOLYL (2 AMINO 8 OXO 9,10 EPOXYDECANOYL) DEXTRO PHENYLALANYL]; HISTONE DEACETYLASE INHIBITOR; IMMUNOSUPPRESSIVE AGENT; KETONE DERIVATIVE; LARGAZOLE; MACROCYCLIC COMPOUND; N (2 AMINOPHENYL) 4 (3 PYRIDINYLMETHOXYCARBONYLAMINOMETHYL)BENZAMIDE; ROMIDEPSIN; SHORT CHAIN FATTY ACID; TRAPOXIN; TRAPOXIN A; TRAPOXIN B; TRICHOSTATIN A; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALPROIC ACID; VORINOSTAT;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER INHIBITION; CELL DIFFERENTIATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HUMAN CELL; NONHUMAN;

ANIMALS; CELL DIFFERENTIATION; CELL PROLIFERATION; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HUMANS; HYDROXAMIC ACIDS; MACROCYCLIC COMPOUNDS;

EID: 77955646151     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802610792232079     Document Type: Article

References (136)

1. Carey, N.; La Thangue, N. B. Histone deacetyalse inhibitors: Gathering pace. Curr. Opin. Pharmacol., 2006, 6, 369-375.
2. Ropero, S.; Esteller, M. The role of histone deacetylases (HDACs) in human cancer. Mol. Oncol., 2007, 1, 19-25.
3. Jenuwein, T.; Allis, C. D. Translating the histone code. Science, 2001, 293, 1074-1080.
4. Strahl, B. D.; Allis, C. D. The language of covalent histone modifications. Nature, 2000, 403, 41-45.
5. Althaus, F. R.; Hofferer, L.; Kleczkowska, H. E.; Malanga, M.; Naegeli, H.; Panzeter, P. L.; Realini, C. A. Histone Shuttling by Poly ADP-Ribosylation. Mol. Cell. Biochem., 1994, 138, 53-59.
6. Shiio, Y.; Eisenman, R. N. Histone Sumoylation is Associated with Transcriptional Repression. Proc. Natl. Acad. Sci. USA, 2003, 100, 13225-13230.
7. Kuo, M. H.; Allis, C. D. Roles of histone acetyltransferases and deacetylases in gene regulation. BioEssays, 1998, 20, 615-626.
8. Grunstein, M. Histone acetylation in chromatin structure and transcription. Nature, 1997, 389, 349-352.
9. Davie, J. R.; Hendzel, M. J. Multiple functions of dynamic his-tone acetylation. J. Cell. Biochem., 1994, 55, 98-105.
10. Barnes, P. J.; Adcock, I. M.; Ito, K. Histone acetylation and deacetylation: importance in inflammatory lung diseases. Eur. Respir. J., 2005, 25, 552-563.
11. Gray, S. G.; Dangond, F. Rationale for the use of histone deace-tylase inhibitors as dual therapeutic modality in multiple schlero-sis. Epigenetics, 2006, 1, 67-75.
12. Grabiec, A. M.; Tak, P. P.; Reedquist, K. A. Targeting histone deacetylase activity in rheumatoid arthritis and asthma as prototypes of inflammatory disease: should we keep Our HATs on? Arthritis Res. Ther., 2008, 10, 226.
13. Saito, A.; Yamashita, T.; Mariko, Y.; Nosaka, Y.; Tsuchiya, K.; Ando, T.; Suzuki, T.; Tsuruo, T.; Nakanishi, O. A synthetic inhibitor of histone deacetylase, MS-275, with marked in vivo anti-tumor activity against human tumors. Proc. Natl. Acad. Sci. USA, 1999, 96, 4592-4597.
14. Glick, R. D.; Swindemen, S. L.; Coffey, D. C.; Rifkind, R. A.; Marks, P. A.; Richon, V. M.; La Quaglia, M. P. Hybrid polar histone deacetylase inhibitor induces apoptosis and CD95/CD95 ligand expression in human neuroblastoma. Cancer Res., 1999, 59, 4392-4399.
15. Butler, L. M.; Agus, D. B.; Scher, H. I.; Higgins, B.; Rose, A.; Cordon-Cardo, C.; Thaler, H. T.; Rifkind, R. A.; Marks, P. A.; Richon, V. M. Suberoylanilide hydroxamic acid, an inhibitor of histone deacetylase, suppresses the growth of prostate cancer cells in vitro and in vivo. Cancer Res., 2000, 60, 5165-5170.
16. Andrews, K. T.; Tran, T. N.; Lucke, A. J.; Kahnberg, P.; Le, G. T.; Boyle, G. M.; Gardiner, D. L.; Skinner-Adams, T. S.; Fairlie, D. P. Potent antimalarial activity of histone deacetylase inhibitor analogues. Antimicrob. Agents Chemother., 2008, 52, 14541461.
17. Agbor-Enoh, S.; Seudieu, C.; Davidson, E.; Dritschilo, A.; Jung, M. Novel inhibitor of plasmodium histone deacetylase that cures P. berghei-infected Mice. Antimicrob. Agents Chemother., 2009, 53, 1727-1734.
18. Dow, G. S.; Chen, Y.; Andrews, K. T.; Caridha, D.; Gerena, L.; Gettayacamin, M.; Johnson, J.; Melendez, V.; Obaldia III, N.; Tran, T. N.; Kozikowski, A. P. Antimalarial activity of phen-ylthiazolyly-bearing hydroxamate-based histone deacetylase inhibitors. Antimicrob. Agents Chemother., 2008, 52, 3467-3477.
19. Mai, A.; Cerbara, I.; Valente, S.; Massa, S.; Walker, L. A.; Tek-wani, B. L. Antimalarial and antileishmanial activities of aroyl-pyrroyl-hydroxyamides, a new class of histone deacetylase inhibitor. Antimicrob. Agents Chemother., 2004, 48, 1435-1436.
20. Vergnes, B.; Vanhille, L.; Ouaissi, A.; Sereno, D. Stage-specific antileishmanial activity of an inhibitor of SIR2 histone deacety-lase. Acta Trop., 2005, 94, 107-115.
21. Patil, V.; Guerrant, W.; Chen, P. C.; Gryder, B.; Benicewicz, D. B.; Khan, S. I.; Tekwani, B. L.; Oyelere, A. K. Antimalarial and antileishmanial activities of histone deacetylase inhibitors with triazole-linked cap group. Bioorg. Med. Chem., 2010, 18(1), 415-425.
22. Langley, B.; Gensert, J. M.; Beal, M. F.; Ratan, R. R. Remodeling chromatin and stress resistance in the central nervous system: histone deacetylase inhibitors as novel and broadly effective neu-roprotective agents. Curr. Drug Targets CNS Neurol. Disord., 2005, 4, 41-50.
23. Petri, S.; Kiaei, M.; Kipiani, K.; Chen, J.; Calingasan, N. Y.; Crow, J. P.; Beal, M. F. Additive neuroprotective effects of a his-tone deacetylase inhibitor and a catalytic antioxidant in a trans-genic mouse model of amyotrophic lateral schlerosis. Neuro-biol. Dis., 2006, 22, 40-49.
24. Leng, Y.; Liang, M. H.; Ren, M.; Marinova, Z.; Leeds, P.; Chuang, D. M. Synergistic neuroprotective effects of lithium and valproic acid or other histone deacetylase inhibitors in neurons: roles of glycogen synthase kinase-3 inhibition. J. Neurosci., 2008, 28, 2576-2588.
25. Riggs, M. G.; Whittaker, R. G.; Neumann, J. R.; Ingram, V. R. n-Butyrate causes histone modification in hela and friend erythroleukemia cells. Nature, 1977, 268, 462-464.
26. Boffa, L. C.; Vidali, G.; Mann, R. S.; Allfrey, V. G. Suppression of histone deacetylation in vivo and in vitro by sodium butyrate. J. Biol. Chem., 1978, 253, 3364-3366.
27. Witt, O.; Lindemann, R. HDAC inhibitors: Magic bullets, dirty drugs or just another targeted therapy. Cancer Lett., 2009, 280, 123-124.
28. Yoshida, M.; Kijima, M.; Akita, M.; Beppu, T. Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A. J. Biol. Chem., 1990, 265, 17174-17179.
29. Kijima, M.; Yoshida, M.; Sugita, K.; Horinouchi, S.; Beppu, T. Trapoxin, an antitumor cyclic tetrapeptide,is an irreversible inhibitor of mammalian histone deacetylase. J. Biol. Chem., 1993, 268, 22429-22435.
30. Marks, P. A.; Richon, V. M.; Rifkind, R. A. Histone deacetylase inhibitors: inducers of differentiation or apoptosis of transformed cells. J. Natl. Cancer Inst., 2000, 92, 1210-1216.
31. Batty, N.; Malouf, G. G.; Issa, J. P. Histone deacetylase inhibitors as anti-neoplastic agents. Cancer Lett., 2009, 280, 192-200.
32. http://www.fda.gov/AboutFDA/CentersOffices/CDER/ucm094952.htm
33. Mann, B. S.; Johnson, J. R.; Cohen, M. H.; Justice, R.; Pazdur, R. FDA Approval summary: vorinostat for treatment of advanced primary cutaneous T-cell lymphoma. Oncologist, 2007, 12, 1247-1252.
34. Miller, T. A.; Witter, D. J.; Belvedere, S. Histone deacetylase inhibitors. J. Med. Chem., 2003, 46, 5097-5116.
35. Finnin, M. S.; Donigian, J. R.; Cohen, A.; Richon, V. M.; Rifkind, R. A.; Marks, P. A.; Breslow, R.; Pavletich, N. P. Structures of a histone deacetlase homologue bound to the TSA and SAHA inhibitors. Nature, 1999, 401, 188-193.
36. Suzuki, T.; Matsuura, A.; Kouketsu, A.; Nakagawa, H.; Miyata, N. Identification of a potent non-hydroxamate histone deacety-lase inhibitor by mechanism-based drug design. Bioorg. Med. Chem. Lett., 2005, 15, 331-335.
37. Samoza, J. R.; Skene, R. J.; Katz, B. A.; Mol, C.; Ho, J. D.; Jennings, A. J.; Luong, C.; Arvai, A.; Buggy, J. J.; Chi, E.; Tang, J.; Sang, B. C.; Verner, E.; Wynands, R.; Leahy, E. M.; Dougan, D. R.; Snell, G.; Navre, M.; Knuth, M. W.; Swanson, R. V.; McRee, D. E.; Tari, L. W. Structural snapshots of human HDAC8 provide insights into the class I histone deacetylases. Structure, 2004, 12, 1325-1334.
38. Mulder, G. J.; Meerman, J. H. Sulfonation and glucoridation as competing pathways in the metabolism of hydroxamic acids: the role of n, o-sulfonation in chemical carcinogenesis of aromatic amines. Envir. HealthPerspect., 1983, 49, 27-38.
39. Vassilou, S.; Mucha, A.; Cuniasse, P.; Georgiadis, D.; Lucet-Levannier, K.; Beau, F.; Kannan, R.; Murphy, G.; Knauper, V.; Rio, M. C.; Basset, P.; Yiotakis, A.; Dive, V. Phosphinic pseudo-tripeptides as potent inhibitors of matrix metalloproteinases: A structure-activity study. J. Med. Chem., 1999, 42, 2610-2620.
40. Taori, K.; Paul, V. J.; Luesch, H. Structure and activity of larga-zole, a potent antiproliferative agent the floridian marine cyano-bacterium symploca Sp. J. Am. Chem. Soc., 2008, 130, 1806-1807.
41. Yoshida, M.; Matsuyama, A.; Komatsu, A.; Nishino, N. From discover to the current generation of histone deacetylase inhibitors. Curr. Med. Chem., 2003, 10, 2351-2358.
42. Furumai, R.; Matsuyama, A.; Kobashi, N.; Lee, K. H.; Nishi-yama, M.; Nakajima, H.; Tanaka, A.; Komatsu, Y.; Nishino, N.; Yoshida, M.; Horinouchi, S. FK228 (depsipeptide) as a natural prodrug that inhibits class I histone deacetylases. Cancer Res., 2002, 62, 4916-4921.
43. Halkidou, K.; Gaughan, L.; Cook, S.; Leung, H. Y.; Neal, D. E.; Robson, C. N. Upregulation and nuclear recruitment of HDAC1 in hormone refractory prostate cancer. Prostate, 2004, 59, 177-189.
44. Choi, J. H.; Kwon, H. J.; Yoon, B. I.; Kim, J. H.; Han, S. U.; Joo, H. J.; Kim, D. Y. Expression profile of histone deacetylase 1 in gastric cancer tissues. Jpn. J. Cancer Res., 2001, 92, 1300-1304.
45. Wilson, E. M.; Rotwein, P. Control of MyoD function during initiation of muscle differentiation by an autocrine signalling pathway activated by insulin-like growth factor-II. J. Biol. Chem., 2006, 281, 13548-13558.
46. Song, J.; Noh, J. H.; Lee, J. H.; Eun, J. W.; Ahn, Y. M.; Kim, S. Y.; Lee, S. H.; Park, W. S.; Yoo, N. J.; Lee, J. Y.; Nam, S. W. Increased expression of histone deacetylase 2 in human gastricn cancer. APMIS, 2005, 113, 264-268.
47. Schuetz, A.; Min, J.; Allali-Hassani, A.; Schapira, M.; Shuen, M.; Loppnau, P.; Mazitschek, R.; Kwiatkowski, N. P.; Lewis, T. A.; Maglathin, R. L.; McLean, T. H.; Bochkarev, A.; Plotnikov, A. N.; Vedadi, M.; Arrowsmith, C. H. Human HDAC7 harbors a class IIA histone deacetylase-specific zinc-binding motif and cryptic deacetylase activity. J. Biol. Chem., 2008, 283, 11355-11363.
48. Vannini, A.; Volpari, C.; Filocamo, G.; Casavola, E. C.; Bru-netti, M.; Renzoni, D.; Chakravarty, P.; Paolini, C.; De Francesco, R.; Gallinari, P.; Steinkuhler, C.; Di Marco, S. Crystal structure of a eukaryotic zinc-dependent histone deacetylase, human HDAC8, complexed with a hydroxamic acid inhibitor. Proc. Natl. Acad. Sci. USA, 2004, 101, 15064-15069.
49. Yurek-George, A.; Cecil, A. R.; Mo, A. H.; Wen, S.; Rogers, H.; Habens, F.; Maeda, S.; Yoshida, M.; Packham, G.; Ganesan, A. The first biologically active synthetic analogues of FK228, the depsipeptide histone deacetylase inhibitor. J. Med. Chem., 2007, 50, 5720-5726.
50. Shute, R. E.; Megumi, K.; Rich, D. H. Conformationally constrained biologically active peptides: tentative identification of the antimitogenic bioactive conformer of the naturally occurring cyclic tetrapeptides. Tetrahedron, 1988, 44, 685-695.
51. Loiseau, N.; Gomis, J. M.; Santolini, J.; Delaforge, M.; Andre, F. Predicting the conformational states of cyclic tetrapeptides. Bio-polymers, 2003, 69(3), 363-385.
52. Meutermans, W. D.; Bourne, G. T.; Golding, S. W.; Horton, D. A.; Campitelli, M. R.; Craik, D.; Scanlon, M.; Smythe, M. L. Difficult macrocyclizations: new strategies for synthesizing highly strained cyclic tetrapeptides. Org. Lett., 2003, 5, 2711-2714.
53. Glenn, M. P.; Kelso, M. J.; Tyndall, J. D.; Fairlie, D. P. Conformationally homogenous cyclic tetrapeptides: useful new three-dimensional scaffolds. J. Am. Chem. Soc., 2003, 125, 640-641.
54. Shivashimpi, G. M.; Amagai, S.; Kato, T.; Nishino, N.; Maeda, S.; Nishino, T. G.; Yoshida, M. molecular design of histone deacetylase inhibitors by aromatic ring shifting in chlamydomycin framework. Bioorg. Med. Chem., 2007, 15, 7830-7839.
55. Oyelere, A. K.; Chen, P. C.; Guerrant, W.; Mwakwari, S. C.; Hood, R.; Zhang, Y.; Fan, Y. Non-peptide macrocyclic histone deacetylase inhibitors. J. Med. Chem., 2009, 52(2), 456-468.
56. Deshmukh, P. H.; Schulz-Fademrecht, C.; Procopiou, P. A.; Vigushin, D. A.; Coombes, R. C.; Barrett, A. G. M. Ring-Closing metathesis in the synthesis of biologically active pepti-domimetics of apicidin A. Adv. Synth. Catal., 2007, 349, 175-183.
57. McLaughlin, F.; La Thangue, N. B. Histone deacetylase inhibitors open new doors in cancer therapy. Biochem. Pharmacol., 68, 1139-1144.
58. Kazantsev, A. G.; Thompson, L. M. Therapeutic application of histone deacetylase inhibitors for central nervous system disorders. Nat. Rev. Drug, Discov., 2008, 7, 854-868.
59. Drummond, D. C.; Noble, C. O.; Kirpotin, D. M.; Guo, Z.; Scott, G. K.; Benz, C. C. Clinical development of histone deacetylase inhibitors as anticancer agents. Annu. Rev. Pharmacol. Toxicol., 45, 495-528.
60. Marson, C. M. Histone deacetylase inhibitors: design, structure-activity relationships and therapeutic implications for cancer. Anticancer Agents Med. Chem., 2009, 9(6), 661-692.
61. Newkirk, T. L.; Bowers, A. A.; Williams, R. M. Discovery, biological activity, synthesis and potential therapeutic utility of naturally occurring histone deacetylase inhibitors. Nat. Prod. Rep., 2009, 26(10), 1293-1320.
62. Kalin, J. H.; Butler, K. V.; Kozikowski, A. P. Creating zinc monkey wrenches in the treatment of epigenetic disorders. Curr. Opin. Chem. Biol., 2009, 13(3), 263-271.
63. Moradeia, O.; Vaisburg, A.; Martell, R. E. Histone Deacetylase Inhibitors in Cancer Therapy: New Compounds and Clinical Update of Benzamide-Type Agents. Curr. Top. Med. Chem., 2008, 8(10), 841-858.
64. Jones, P.; Steinkuhler, C. From natural products to small molecule ketone histone deacetylase inhibitors: development of new class specific agents. Curr. Pharm. Des., 2008, 14(6), 545-561.
65. Bieliauskas, A. V.; Pflum, M. K. H. Isoform-selective histone deacetylase inhibitors. Chem. Soc. Rev., 2008, 37, 1402-1413.
66. Townsend, P. A.; Crabb, S. J.; Davidson, S. M.; Johnson, P. W. M.; Packham, G.; Ganesan, A. The Bicyclic Depsipeptide Family of Histone Deacetylase Inhibitors. In: Chemical Biology. From Small Molecules to System Biology and Drug Design, Schreiber, S. L.; Kapoor, T. M.; Wess, G. Eds.; Wiley-VCH Weinheim, 2007; Vol. 2, pp 693-720.
67. Chorev, M.; Goodman, M. A dozen years of retro-inverso pepti-domimetics. Acc. Chem. Res., 1993, 26(5), 266-273.
68. Nielsen, T. K.; Hildmann, C.; Dickmanns, A.; Schwienhorst, A.; Ficner, R. Crystal structure of a bacterial class 2 histone deacetylase homologue. J. Mol. Biol., 2005, 354(1), 107-120.
69. Kozikowski, A. P.; Butler, K. V. Chemical origins of isoform selectivity in histone deacetylase inhibitors. Curr. Pharm. Des., 2008, 14, 505-528.
70. Suzuki, T.; Itoh, Y.; Miyata, N. Isoform-selective histone deacetylase inhibitors. Curr. Pharm. Des. 2008, 14, 529-544.
71. Gross, M. L.; McCrery, D.; Crow, F.; Tomer, K. B. The structure of the toxin from Helminthosporium carbonum. Tetrahedron Lett. 1982, 23, 5381-5384.
72. Liesch, J. M.; Sweeley, C. C.; Staffeld, G. D.; Anderson, M. S.; Weber, D. J.; Scheffer, R. P. Structure of HC-toxin, a cyclic tetrapeptide from Helminthosporium carbonum. Tetrahedron Lett., 1982, 38, 45-48.
73. Kim, S.-D.; Knoche, H. W. Structure of an amino acid analog of the host-specific toxin from Helminthosporium carbonum. Tetrahedron Lett., 1985, 26, 969-972.
74. Tanis, S. P.; Horenstein, B. A.; Scheffer, R. P.; Rasmussen, J. B. A new host specific toxin from Helminthosporium carbonum. Heterocycles, 1986, 24, 3423-3431.
75. Hirota, A.; Suzuki, A.; Suzuki, H.; Aizawa, K.; Tamura, S. Structure of Cyl-2, a novel cyclotetrapeptide from Cylindrocla-dium scoparium. Agric. Biol. Chem., 1973, 37, 955-956.
76. Hirota, A.; Suzuki, A.; Suzuki, H.; Tamura, S. Isolation and biological activity of Cyl-2, a metabolite of Cylindrocladium scoparium. Agric. Biol. Chem., 1973, 37, 643-647.
77. Hirota, A.; Suzuki, A.; Suzuki, H.; Tamura, S. Characteriza-tionof four amino acids constituting Cyl-2, a metabolite from Cylindrocladium scoparium. Agric. Biol. Chem., 1973, 37, 1185-1189.
78. Kawai, M.; Pottorf, R. S.; Rich, D. H. Structure and solution conformation of the cytostatic cyclic tetrapeptide WF-3161, cy-clo-[L-leucyl-L-pipecolyl-L-(2-amino-8-oxo-9,10-epoxydeca-noyl)-D-phenylalanyl]. J. Med. Chem., 1986, 29, 2409-2411.
79. Umehara, K.; Nakahara, K.; Kiyoto, S.; Iwami, M.; Okamoto, M.; Tanaka, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. Studies on WF-3161, a new antitumor antibiotic. J. Antibiot., 1983, 36, 478-483.
80. Closse, A.; Huguenin, R. Isolation and structural clarification of chlamydocin. Helv. Chim. Acta, 1974, 57(3), 533-545.
81. Itazaki, H.; Nagashima, K.; Sugita, K.; Yoshida, H.; Kawamura, Y.; Yasuda, Y.; Matsumoto, K.; Ishii, K.; Uotani, N.; Nakai, H.; Terui, A.; Yoshimatsu, S.; Ikenishi, Y.; Nakawaga, Y. Isolation and structural elucidation of new cyclotetrapeptides, trapoxin A and B, having detransformation activities as antitumor agents. J. Antibiot., 1990, 63, 1524-1532.
82. Ciuffetti, L. M.; Pope, M. R.; Dunkle, L. D.; Daly, J. M.; Kno-che, H. W. Isolation and structure of an inactive product derived from the host-specific toxin produced by Helminthosporium car-bonum. Biochemistry, 1983, 22(14), 3507-3510.
83. Hildmann, C.; Wegener, D.; Riester, D.; Hempel, R.; Schober, A.; Merana, J.; Giurato, L.; Guccione, S.; Nielsen, T. K.; Ficner, R.; Schwienhorst, A. Substrate and inhibitor specificity of class 1 and class 2 histone deacetylases. J. Biotechnol. 2006, 124(1), 258-270.
84. Furumai, R.; Komatsu, Y.; Nishino, N.; Khochbin, S.; Yoshida, M.; Horinouchi, S. Potent histone deacetylase inhibitors built from trichostatin A and cyclic tetrapeptide antibiotics including trapoxin. Proc. Natl. Acad. Sci. USA, 2001, 98, 87-92.
85. Darkin-Rattray, S. J.; Gurnett, A. M.; Myers, R. W.; Dulski, P. M.; Crumley, T. M.; Allocco, J. J. Apicidin: A novel antiproto-zoal agent that inhibits parasite histone deacetylase. Proc. Natl. Acad. Sci. USA, 1996, 93(23), 13143-13147.
86. Han, J.-W.; Ahn, S. H.; Park, S. H.; Wang, S. Y.; Bae, G.-U.; Seo, D.-W. Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and Gelsolin Cancer Res., 2000, 60(21), 6068-6074.
87. Kwon, S. H.; Ahn, S. H.; Kim, Y. K.; G. -U. Bae; Yoon, J. W.; Hong, S. Apicidin, a histone deacetylase inhibitor, induces apop-tosis and Fas/Fas ligand expression in human-acute promyelocytic leukemia cells. J. Biol. Chem., 2002, 277, 2073-2080.
88. Singh, S. B.; Zink, D. L.; Liesch, J. M.; Mosley, R. T.; Dom-browski, A. W.; Bills, G. F. Structure and chemistry of apicidins, a class of novel cyclic tetrapeptides without a terminal a-keto epoxide as inhibitors of histone deacetylase with potent antiprotozoal activities. J. Org. Chem., 2002, 67(3), 815-825.
89. Singh, S. B.; Zink, D. L.; Polishook, J. D.; Dombrowski, A. W.; Darkin-Rattray, S. J.; Schmatz, D. M.; Goetz, M. A. Apicidins: Novel cyclic tetrapeptides as coccidiostats and antimalarial agents from Fusarium pallidoroseum. Tetrahedron Lett., 1996, 37(45), 8077-8080.
90. Colletti, S. L.; Myers, R. W.; Darkin-Rattray, S. J.; Gurnett, A. M.; Dulski, P. M.; Galuska, S.; Allocco, J. J.; Ayer, M. B.; Li, C.; Lim, J.; Crumley, T. M.; Cannova, C.; Schmatz, D. M.; Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T. Broad spectrum an-tiprotozoal agents that inhibit histone deacetylase: structure-activity relationships of apicidin. Part 1. Bioorg. Med. Chem. Lett., 2001, 11(2), 107-111.
91. Komatsu, Y.; Tomizaki, K.; Tsukamoto, M.; Kato, T. Cyclic Hydroxamic-acid-containing Peptide 31, a potent synthetic his-tone deacetylase inhibitor with antitumor activity. Cancer Res., 2001, 61, 4459-4466.
92. Horne, W. S.; Olsen, C. A.; Beierle, J. M.; Montero, A.; Ghadiri, M. R. Probing the bioactive conformation of an archetypal natural product HDAC inhibitor with conformationally homogeneous triazole-modified cyclic tetrapeptides. Angew. Chem. Int. Ed., 2009, 48(26), 4718-4724.
93. Nakao, Y.; Yoshida, S.; Matsunaga, S.; Shindoh, N.; Terada, Y.; Nagai, K.; Yamashita, J. K.; Ganesan, A.; van Soest, R. W. M.; Fusetani, N. Azumamides A-E: Histone deacetylase inhibitory cyclic tetrapeptides from the marine sponge mycale izuensis. Angew. Chem. Int. Ed, 2006, 45(45), 7553-7557.
94. Maulucci, N.; Chini, M. G.; Di Micco, S.; Izzo, I.; Cafaro, E.; Russo, A.; Gallinari, P.; Paolini, C.; Nardi, M. C.; Casapullo, A.; Riccio, R.; Bifulco, G.; De Riccardis, F. Molecular insights into azumamide e histone deacetylases inhibitory activity. J. Am. Chem. Soc., 2007, 129(10), 3007-3012.
95. Chandrasekhar, S.; Rao, C. L.; Seenaiah, M.; Naresh, P.; Jagadeesh, B.; Manjeera, D.; Sarkar, A.; Bhadra, M. P. Total synthesis of azumamide E and sugar amino acid-containing analogue. J. Org. Chem., 2009, 74(1), 401-404.
96. Wen, S.; Carey, K. L.; Nakao, Y.; Fusetani, N.; Packham, G.; Ganesan, A. Total synthesis of azumamide a and azumamide e, evaluation as histone deacetylase inhibitors, and design of a more potent analogue. Org. Lett., 2007, 9(6), 1105-1108.
97. Nishino, N.; Jose, B.; Shinta, R.; Kato, T.; Komatsu, Y.; Yoshida, M. Chlamydocin-hydroxamic acid analogues as histone deacetylase inhibitors. Bioorg. Med. Chem., 2004, 12, 5777-5784.
98. Ueda, H.; Nakajima, H.; Hori, Y.; Fujita, T.; Nishimura, M.; Goto, T.; Okuhara, M. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum no. 968. J. Antibiot., 1994, 47, 301-310.
99. Shigematsu, N.; Ueda, H.; Takase, S.; Tanaka, H. FR9011228, a novel antitumor bicyclic depsipeptide produced by chromobacte-rium violaceum no. 968. J. Antibiot., 1994, 47, 311-314.
100. Sandor, V.; Bakke, S.; Robey, R. W.; Kang, M. H.; Blagosk-lonny, M. V.; Bender, J.; Brooks, R.; Piekarz, R. L.; Tucker, E.; Figg, W. D.; Chan, K. K.; Goldspiel, B.; Fojo, A. T.; Balcerzak, S. P.; Bates, S. E. Phase I trial of the histone deacetylase inhibitor, depsipeptide (FR901228, NSC 630176), in patients with refractory neoplasms. Clin. Cancer Res., 2002, 8, 718-728.
101. Marshall, J. L.; Rizvi, N.; Kauh, J.; Dahut, W.; Figuera, M. A phase I trial of depsipeptide (FR901228) in patients with advanced cancer. J. Exp. Ther. Oncol., 2002, 2, 325-332.
102. Masuoka, Y.; Nagai, A.; Shin-ya, K.; Furihata, K.; Nagai, K.; Suzuki, K.-I.; Hayakawa, Y.; Seto, H. Spiruchostatins A and B, novel gene expression-enhancing substances produced by pseu-domonas sp. Tetrahedron Lett., 2001, 42, (1), 41-44.
103. Lijima, Y.; Munakata, A.; Shin-ya, K.; Ganesan, A.; Doi, T.; Takahashi, T. A solid-phase total synthesis of the cyclic dep-sipeptide HDAC inhibitor spiruchostatin A. Tetrahedron Lett., 2009, 50(24), 2970-2972.
104. Calandra, N. A.; Cheng, Y. L.; Kocak, K. A.; Miller, J. S. Total synthesis of spiruchostatin A via chemoselective macrocycliza-tion using an accessible enantiomerically pure latent thioester. Org. Lett., 2009, 77(9), 1971-1974.
105. Takizawa, T.; Watanabe, K.; Narita, K.; Kudo, K.; Oguchi, T.; Abe, H.; Katoh, T. Total synthesis of spiruchostatin A, a potent histone deacetylase inhibitor. Heterocycles, 2008, 76(1), 275-290.
106. Takizawa, T.; Watanabe, K.; Narita, K.; Oguchi, T.; Abe, H.; Katoh, T. Total synthesis of spiruchostatin B, a potent histone deacetylase inhibitor, from a microorganism. Chem. Commun., 2008, 14, 1677-1679.
107. Yurek-George, A.; Habens, F.; Brimmell, M.; Packham, G.; Ganesan, A. Total synthesis of spiruchostatin A, a potent histone deacetylase inhibitor. J. Am. Chem. Soc., 2004, 726(4), 1030-1031.
108. Narita, K.; Kikuchi, T.; Watanabe, K.; Takizawa, T.; Oguchi, T.; Kudo, K.; Matsuhara, K.; Abe, H.; Yamori, T.; Yoshida, M.; Ka-toh, T. Total synthesis of the bicyclic depsipeptide HDAC inhibitors spiruchostatins A and B, 5″-epi-spiruchostatin B, FK228 (FR901228) and preliminary evaluation of their biological activity. Chem. Eur. J., 2009, 75, 11174-11186.
109. Bowers, A.; West, N.; Taunton, J.; Schreiber, S. L.; Bradner, J. E.; Williams, R. M. Total synthesis and biological mode of action of largazole: a potent class I histone deacetylase inhibitor. J. Am. Chem. Soc. 2008, 750(33), 11219-11222.
110. Ying, Y.; Taori, K.; Kim, H.; Hong, J.; Luesch, H. Total synthesis and molecular target of largazole, a histone deacetylase inhibitor. J. Am. Chem. Soc., 2008, 730(26), 8455-8459.
111. Ghosh, A. K.; Kulkarni, S. Enantioselective total synthesis of (+)-largazole, a potent inhibitor of histone deacetylase. Org. Lett., 2008, 70(17), 3907-3909.
112. Bowers, A. A.; Greshock, T. J.; West, N.; Estiu, G.; Schreiber, S. L.; Wiest, O.; Williams, R. M.; Bradner, J. E. Synthesis and conformation-activity relationships of the peptide isosteres of FK228 and largazole. J. Am. Chem. Soc., 2009, 737(8), 2900-2905.
113. Seiser, T.; Kamena, F.; Cramer, N. Synthesis and biological activity of largazole and derivatives. Angew. Chem. Int. Ed., 47, 6483-6485.
114. Bowers, A.; West, N.; Newkirk, T.; Troutman-Youngman, A.; Schreiber, S. L.; Wlest, O.; Bradner, J.; Williams, R. Synthesis and histone deacetylase inhibitory activity of largazole analogs: alteration of the zinc-binding domain and macrocyclic scaffold. Org. Lett., 2009, 77(16), 1301-1304.
115. Chen, F.; Gao, A.-H.; Li, J.; Nan, F.-J. Synthesis and biological evaluation of C7-demethyl largazole analogues. Chem Med Chem, 4, 1269-1272.
116. Ying, Y.; Liu, Y.; Byeon, S. R.; Kim, H.; Luesch, H.; Hong, J. Synthesis and activity of largazole analogues with linker and macrocycle modification. Org. Lett., 2008, 70(18), 4021-4024.
117. Curtin, M. L.; Garland, R. B.; Heyman, H. R.; Frey, R. R.; Michaelides, M. R.; Li, J.; Pease, L. J.; Glaser, K. B.; Marcotte, P. A.; Davidsen, S. K. Succinimide hydroxamic acids as potent inhibitors of histone deacetylase (HDAC). Bioorg. Med. Chem., 2002, 72(20), 2919-2923.
118. Liu, T.; Kapustin, G.; Etzkorn, F. A. Design and synthesis of a potent histone deacetylase inhibitor. J. Med. Chem., 2007, 50(9), 2003-2006.
119. Pirali, T.; Faccio, V.; Mossetti, R.; Grolla, A. A.; Micco, S. D.; Bifulco, G.; Genazzani, A. A.; Tron, G. C. Synthesis, molecular docking and biological evaluation as HDAC inhibitors of cy-clopeptide mimetics by a tandem three-component reaction and intramolecular [3+2] cycloaddition. Mol. Divers., 2010, 74, 109-121.
120. Randolph, J. T.; Waid, P.; Nichols, C.; Sauer, D.; Haviv, F.; Diaz, G.; Bammert, G.; Besecke, L. M.; Segreti, J. A.; Mohning, K. M.; Bush, E. N.; Wegner, C. D.; Greer, J. Nonpeptide lu-teinizing hormone-releasing hormone antagonists derived from erythromycin a: design, synthesis, and biological activity of clad-inose replacement analogues. J. Med. Chem., 2004, 47(5), 1085-1097.
121. Chen, P. C.; Patil, V.; Guerrant, W.; Green, P.; Oyelere, A. K. Synthesis and structure-activity relationship of histone deacety-lase (HDAC) inhibitors with triazole-linked cap group. Bioorg. Med. Chem., 2008, 76(9), 4839-4853.
122. Mwakwari, S. C.; Guerrant, W.; Patil, V.; Khan, S. I.; Tekwani, B. L.; Oyelere, A. K. Non-peptide macrocyclic histone deacety-lase inhibitors derived from tricyclic ketolide skeleton. Manuscript under review, 2010.
123. Oku, N.; Nagai, K.; Shindoh, N.; Terada, Y.; Soest, R. W. M. V.; Matsunaga, S.; Fusetani, N. Three new cyclostellettamines, which inhibit histone deacetylase, from a marine sponge of the genus Xestospongia. Bioorg. Med. Chem. Lett., 2004, 74(10), 2617-2620.
124. Fusetani, N.; Asai, N.; Matsunaga, S.; Honda, K.; Yasumuro, K. Cyclostellettamines A-F, pyridine alkaloids which inhibit binding of methyl quinuclidinyl benzilate (QNB) to muscarinic ace-tylcholine receptors, from the marine sponge, Stelletta maxima. Tetrahedron Lett., 1994, 35(23), 3967-3970.
125. Piekarz, R. L.; Robey, R.; Sandor, V.; Bakke, S.; Wilson, W. H.; Dahmoush, L.; Kingma, D. M.; Turner, M. L.; Altemus, R.; Bates, S. E. Inhibitor of histone deacetylation, depsipeptide (FR901228), in the treatment of peripheral and cutaneous T-cell lymphoma: a case report. Blood, 2001, 98(9), 2865-2868.
126. Harrison, S. J.; Quach, H.; Yuen, K. High response rates with the combination of bortezomib, dexamethasone and the pan-histone deacetylase inhibitor romidepsin in patients with relapsed or refractory multiple myeloma in a phase I/II clinical trial. ASH Ann. Meet. Abstr., 2008, 772, 3698.
127. Doss, H. H.; Jones, S. F.; nfante, J. R.; Spigel, D. R.; Willcutt, N.; Lamar, R.; Barton, J.; Keegan, M.; Burris III, H. A. A phase I trial of romidepsin in combination with gemcitabine in patients with pancreatic and other advanced solid tumors. J. Clin. Oncol., 2008, 26(15S), 2567.
128. Whitehead, R. P.; Rankin, C.; Hoff, P. M.; Gold, P. J.; Billingsley, K. G.; Chapman, R. A.; Wong, L.; Ward, J. H.; Abbruzzese, J. L.; Blanke, C. D. 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, 2008, 27, 469-475.
129. Byrd, J. C.; Marcucci, G.; Parthun, M. R.; Xiao, J. J.; Klisovic, R. B.; Moran, M.; Lin, T. S.; Liu, S.; Sklenar, A. R.; Davis, M. E.; Lucas, D. M.; Fischer, B.; Shank, R.; Tejaswi, S. L.; Binkley, P.; Wright, J.; Chan, K. K.; Grever, M. R. A phase 1 and phar-macodynamic study of depsipeptide (FK228) in chronic lympho-cytic leukemia and acute myeloid leukemia. Blood, 2005, 705, 959-967.
130. Schrump, D. S.; Fischette, M. R.; Nguyen, D. M.; Zhao, M.; Li, X.; Kunst, T. F.; Hancox, A.; Hong, J. A.; Chen, G. A.; Kruchin, E.; Wright, J. J.; Rosing, D. R.; Sparreboom, A.; Figg, W. D.; M. S. S. Clinical and molecular responses in lung cancer patients receiving romidepsin. Clin. Cancer Res., 2008, 14, 188-198.
131. Klimek, V. M.; Fircanis, S.; Maslak, P.; Guernah, I.; Baum, M.; Wu, N.; Panageas, K.; Wright, J. J.; Pandolfi, P. P.; Nimer, S. D. Tolerability, pharmacodynamics, and pharmacokinetics studies of depsipeptide (romidepsin) in patients with acute myelogenous leukemia or advanced myelodysplastic syndromes. Clin. Cancer Res., 2008, 14, 826-832.
132. Shah, M. H.; Binkley, P.; Chan, K.; Xiao, J.; Arbogast, D.; Col-lamore, M.; Farra, Y.; Young, D.; Grever, M. Cardiotoxicity of histone deacetylase inhibitor depsipeptide in patients with metas-tatic neuroendocrine tumors. Clin. Cancer Res., 2006, 12, 3997-4003.
133. Molife, L. R.; Attard, G.; Fong, P. C.; Karavasilis, V.; Reid, A. H.; Patterson, S.; Riggs Jr, C. E.; Higano, C.; Stadler, W. M.; McCulloch, W.; Dearnaley, D.; Parker, C.; de Bono, J. S. Phase II, two-stage, single-arm trial of the histone deacetylase inhibitor (HDACi) romidepsin in metastatic castration-resistant prostate cancer (CRPC). Ann. Oncol., 2009, 21, 109-113.
134. Shah, M. H.; Villalona-Calero, M. A.; Marcucci, G.; Byrd, J.C.; Grever, M.R. HDAC inhibitors and cardiac safety. Clin. Cancer Res., 2007, 13, 1068.
135. Prince, H. M.; Bishton, M. J.; Harrison, S. J. Clinical studies of histone deacetylase inhibitors. Clin. Cancer Res., 2009, 15, 3958-3969.
136. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncemen ts/ucm 189629.htm, 2009.