Design and synthesis of mono and bicyclic tetrapeptides thioester as potent inhibitor of histone deacetylases

Amino Acids

Volumn 46, Issue 10, 2014, Pages 2435-2444

  Hoque, Md Ashraful ^a,b,c   Islam, Md Shahidul ^b,c   Islam, Md Nurul ^b,c   Kato, Tamaki ^c   Nishino, Norikazu ^c   Ito, Akihiro ^d   Yoshida, Minoru ^d  

^a UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^b UNIVERSITY OF RAJSHAHI   (Bangladesh)

^c KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

^d RIKEN   (Japan)

Author keywords

Bicyclic tetrapeptides; Depsipeptide; Histone deacetylase inhibitors; Largazole

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOPEPTIDE; HDAC1 PROTEIN, HUMAN; HDAC4 PROTEIN, HUMAN; HDAC6 PROTEIN, MOUSE; HISTONE DEACETYLASE; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE INHIBITOR; ISOENZYME; OLIGOPEPTIDE; PRODRUG; PROTEIN P21; RECOMBINANT PROTEIN; REPRESSOR PROTEIN;

ANIMAL; ANTAGONISTS AND INHIBITORS; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; DRUG DESIGN; DRUG EFFECTS; GENETICS; HEK293 CELL LINE; HUMAN; METABOLISM; MINK; MOUSE; OSMOLARITY; PROMOTER REGION; REPORTER GENE; SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE; DRUG DESIGN; GENES, REPORTER; HEK293 CELLS; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HUMANS; ISOENZYMES; MICE; MINK; MOLECULAR STRUCTURE; OLIGOPEPTIDES; OSMOLAR CONCENTRATION; PEPTIDES, CYCLIC; PRODRUGS; PROMOTER REGIONS, GENETIC; PROTO-ONCOGENE PROTEINS P21(RAS); RECOMBINANT PROTEINS; REPRESSOR PROTEINS;

EID: 84925260098     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-014-1800-5     Document Type: Article

References (25)

1. Archer SY, Hodin RA (1999) Histone acetylation and cancer. Curr Opin Genet Dev 9:171-174. doi: 10.1016/S0959-437X(99)80026-4->
2. Bhuiyan MPI, Kato T, Okauchi T et al (2006) Chlamydocin analogs bearing carbonyl group as possible ligand toward zinc atom in histone deacetylases. Bioorg Med Chem 14:3438-3446. doi: 10.1016/j.bmc.2005.12.063
3. Butler KV, Kozikowski AP (2008) Chemical origins of isoform selectivity in histone deacetylase inhibitors. Curr Pharm Des 14:505-528. doi: 10.2174/138161208783885353
4. Cress WD, Seto E (2000) Histonedeacetylases, transcriptional control and cancer. J Cell Physiol 184:1-16
5. Dickinson M, Prince HM (2012) Romidepsin for relapsed and refractory cutaneous T-cell lymphoma clinical medicine insights. Dermatology 5:21-28. doi: 10.4137/CMD.S7252
6. Frey RR, Wada CK, Garland RB (2002) Trifluoromethyl ketones as inhibitors of histone deacetylase. Bioorg Med Chem Lett 12:3443-3447. doi: 10.1016/S0960-894X(02)00754-0
7. Furumai R, Matsuyama A, Kobashi M (2002) FK228 (depsipeptide) as a natural prodrug that inhibits class 1 histone deacetylases. Cancer Res 62:4916-4921
8. Grozinger CM, Schreiber SL (2002) Deacetylase enzymes: biological functions and the use of small-molecule inhibitors. Chem Biol 9:3-16
9. Hassig CA, Schreiber SL (1997) Nuclear histone acetylases and deacetylases and transcriptional regulation: HATs off to HDACs. Curr Opin Chem Biol 1:300-308. doi: 10.1016/S1367-5931(97)80066-X
10. Hoque AH, Yoshida M et al (2012) Cyclic tetrapeptides with thioacetate tails or intramolecular disulfide bridge as potent inhibitors of histone deacetylases. Bioorg Med Chem Lett 22:6770-6772. doi: 10.1016/j.bmcl.2012.03.004
11. Islam NM, Nishino N et al (2010) Bicyclic peptides as potent inhibitors of histone deacetylases: optimization of alkyl loop length. Bioorg Med Chem Lett 20:997-999. doi: 10.1016/j.bmcl.2009.12.054
12. Kouzarides T (1999) Histone acetylases and deacetylases in cell proliferation. Curr Opin Genet Dev 9:40-48
13. Mahlknecht U, Ottmann OG, Hoelzer D (2000) When the band begins to play: histone acetylation caught in the crossfire of gene control. Mol Carcinog 27:268-271. doi: 10.1002/(SICI)1098-2744(200004
14. Mann BS, Johnson JR et al (2007) FDA approval summary: vorinostat for treatment of advanced primary cutaneous T-cell lymphoma. Oncologist 12:1247-1252. doi: 10.1634/theoncologist.12-10-1247
15. Michaelides MR, Dellaria JF, Gong J et al (2001) Biaryl ether retrohydroxamates as potent, long-lived, orally bioavailable MMP inhibitors. Bioorg Med Chem Lett 11:1553-1556. doi: 10.1016/S0960-894X(01)00031-2
16. Mulder GJ, Meerman JH (1983) Sulfation and glucuronidation as competing pathways in the metabolism of hydroxamic acids: the role of N, O-sulfonation in chemical carcinogenesis of aromatic amines. Environ Health Perspect 49:27-32
17. Nishino N, Jose B, Okamura S et al (2003) Cyclic Tetrapeptides bearing a sulfhydryl group potently inhibit histone deacetylases. Org Lett 5:5079-5082. doi: 10.1021/ol036098e
18. Nishino N, Jose B et al (2004) Chlamydocin-hydroxamic acid analogues as histone deacetylase inhibitors. Bioorg Med Chem 12:5777-5784. doi: 10.1016/j.bmc.2004.08.041
19. Nishino N, Shivashimpi GM et al (2008) Interaction of aliphatic cap group in inhibition of histone deacetylases by cyclic tetrapeptides. Bioorg Med Chem 16:437-445. doi: 10.1016/j.bmc.2007.09.021
20. Shivashimpi GM, Amagai S, Kato T et al (2007) Molecular design of histone deacetylase inhibitors by aromatic ring shifting in chlamydocin framework. Bioorg Med Chem 15:7830-7839. doi: 10.1016/j.bmc.2007.08.041
21. Suzuki T, Kouketsu A, Itoh Y et al (2006) Highly potent and selective histone deacetylase 6 inhibitors designed based on small-molecular substrate. J Med Chem 49:4809-4812. doi: 10.1021/jm060554y
22. Taori K, Paul VJ, 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. doi: 10.1021/ja7110064
23. Watanabe LA, Jose B, Kato T, Nishino N, Yoshida M (2004) Synthesis of L-a-amino-w-bromoalkanoic acid for side chain modification. Tetrahedron Lett 45(3):491-494. doi: 10.1016/j.tetlet.2003.11.007
24. Yoshida M, Matsuayama A, Komatsu Y, Nishino N (2003) From discovery to the coming generation of histone deacetylase inhibitors. Curr Med Chem 10:2351-2358. doi: 10.2174/092986708784049612
25. Zain J, Kaminetzky D, O'Connor OA (2010) Emerging role of epigenetic therapies in cutaneous T-cell lymphomas. Expert Rev Hematol 3:187-203. doi: 10.1586/ehm.10.9