8,492
Views
139
CrossRef citations to date
0
Altmetric
Review Article

Zinc binding groups for histone deacetylase inhibitors

, , , &
Pages 714-721 | Received 04 Oct 2017, Accepted 11 Dec 2017, Published online: 04 Apr 2018

References

  • Bernstein BE, Tong JK, Schreiber SL. Genomewide studies of histone deacetylase function in yeast. Proc Natl Acad Sci USA 2000;97:13708–13.
  • De Ruijter AJM, Van Gennip AH, Caron HN, et al. Histone deacetylases (HDACs): characterization of the classical HDAC family. Biochem J 2003;370:737–49.
  • Foglietti C, Filocamo G, Cundari E, et al. Dissecting the biological functions of Drosophila histone deacetylases by RNA interference and transcriptional profiling. J Biol Chem 2006;281:17968–76.
  • Soragni E, Xu C, Cooper A, et al. Evaluation of histone deacetylase inhibitors as therapeutics for neurodegenerative diseases. Method Mol Biol 2011;793:495–508.
  • Mai A, Rotili D, Valente S, Kazantsev AG. Histone deacetylase inhibitors and neurodegenerative disorders: holding the promise. Curr Pharm Design 2009;15:3940–57.
  • Roger T, Lugrin J, Le Roy D, et al. Histone deacetylase inhibitors impair innate immune responses to Toll-like receptor agonists and to infection. Blood 2011;117:1205–17.
  • Valenzuela-Fernandez A, Alvarez S, Gordon-Alonso M, et al. Histone deacetylase 6 regulates human immunodeficiency virus type 1 infection. Mol Biol Cell 2005;16:5445–54.
  • Saiyed ZM, Gandhi N, Agudelo M, et al. HIV-1 Tat upregulates expression of histone deacetylase-2 (HDAC2) in human neurons: implication for HIV-associated neurocognitive disorder (HAND). Neurochem Int 2011;58:656–64.
  • Margolis DM. Histone deacetylase inhibitors and HIV latency. Curr Opin HIV AIDS 2011;6:25–9.
  • Ylisastigui L, Archin NM, Lehrman G, et al. Coaxing HIV-1 from resting CD4 T cells: histone deacetylase inhibition allows latent viral expression. Aids 2004;18:1101–8.
  • Gallo P, Latronico MV, Gallo P, et al. Inhibition of class I histone deacetylase with an apicidin derivative prevents cardiac hypertrophy and failure. Cardiovasc Res 2008;80:416–24.
  • Kook H, Lepore JJ, Gitler AD, et al. Cardiac hypertrophy and histone deacetylase-dependent transcriptional repression mediated by the atypical homeodomain protein Hop. J Clin Invest 2003;112:863–71.
  • Marks PA, Rifkind RA, Richon VM, et al. Histone deacetylases and cancer: causes and therapies. Nat Rev Cancer 2001;1:194–202.
  • Richon VM, Emiliani S, Verdin E, et al. A class of hybrid polar inducers of transformed cell differentiation inhibits histone deacetylases. Proc Natl Acad Sci USA 1998;95:3003–7.
  • Ueda H, Nakajima H, Hori Y, et al. Fr901228, a novel antitumor bicyclic depsipeptide produced by chromobacterium-violaceum No-968.1. Taxonomy, fermentation, isolation, physicochemical and biological properties, and antitumor-activity. J Antibiot 1994;47:301–10.
  • Yang L, Xue XW, Zhang YH. Simple and efficient synthesis of belinostat. Syn Commun 2010;40:2520–4.
  • Neri P, Bahlis NJ, Lonial S. Panobinostat for the treatment of multiple myeloma. Expert Opin Investig Drugs 2012;21:733–47.
  • Manal M, Chandrasekar MJN, Priya JG, Nanjan MJ. Inhibitors of histone deacetylase as antitumor agents: a critical review. Bioorg Chem 2016;67:18–42.
  • Roche J, Bertrand P. Inside HDACs with more selective HDAC inhibitors. Eur J Med Chem 2016;121:451–83.
  • Zhang L, Han YT, Jiang QX, et al. Trend of histone deacetylase inhibitors in cancer therapy: isoform selectivity or multitargeted strategy. Med Res Rev 2015;35:63–84.
  • Clawson GA. Histone deacetylase inhibitors as cancer therapeutics. Ann Transl Med 2016;4:287
  • 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;265:17174–9.
  • Bian J, Zhang LH, Han YT, et al. Histone deacetylase inhibitors: potent anti-leukemic agents. Curr Med Chem 2015;22:2065–74.
  • Giannini G, Cabri W, Fattorusso C, Rodriquez M. Histone deacetylase inhibitors in the treatment of cancer: overview and perspectives. Future Med Chem 2012;4:1439–60.
  • Benedetti R, Conte M, Altucci L. Targeting histone deacetylases in diseases: where are we? Antioxid Redox Signal 2015;23:99–126.
  • Kazantsev AG, Thompson LM. Therapeutic application of histone deacetylase inhibitors for central nervous system disorders. Nat Rev Drug Discov 2008;7:854–68.
  • Dong M, Ning Z, Newman MJ, et al. Phase I study of chidamide (CS055/HBI-8000), a novel histone deacetylase inhibitor, in patients with advanced solid tumors and lymphomas. J Clin Oncol 2009;27:3529a.
  • Gojo I, Jiemjit A, Trepel JB, et al. Phase 1 and pharmacologic study of MS-275, a histone deacetylase inhibitor, in adults with refractory and relapsed acute leukemias. Blood 2007;109:2781–90.
  • Hauschild A, Trefzer U, Garbe C, et al. A phase II multicenter study on the histone deacetylase (HDAC) inhibitor MS-275, comparing two dosage schedules in metastatic melanoma. J Clin Oncol 2006;24:463s.
  • Gojo I, Gore SD, Jiemjit A, et al. Phase I study of histone deacetylase inhibitor (HDI) MS-275 in adults with refractory or realpsed hematologic malignancies. Blood 2003;102:388a.
  • Connolly RM, Jankowitz RA, Zahnow CA, et al. A phase 2 study investigating the safety, efficacy and surrogate biomarkers of response of 5-azacitidine (5-AZA) and entinostat (MS-275) in patients with advanced breast cancer. Cancer Res 2011;71:Abstract nr OT3-01-06.
  • Bonfils C, Kalita A, Dubay M, et al. Evaluation of the pharmacodynamic effects of MGCD0103 from preclinical models to human using a novel HDAC enzyme assay. Clin Cancer Res 2008;14:3441–9.
  • Martell RE, Younes A, Assouline SE, et al. Phase II study of MGCD0103 in patients with relapsed follicular lymphoma (FL): study reinitiation and update of clinical efficacy and safety. J Clin Oncol 2010;28:8086a.
  • Blum KA, Advani A, Fernandez L, et al. Phase II study of the histone deacetylase inhibitor MGCD0103 in patients with previously treated chronic lymphocytic leukaemia. Br J Haematol 2009;147:507–14.
  • Garcia-Manero G, Assouline S, Cortes J, et al. Phase 1 study of the oral isotype specific histone deacetylase inhibitor MGCD0103 in leukemia. Blood 2008;112:981–9.
  • DiPersio J, Stadtmauer EA, Nademanee AP, et al. Investigators, Phase I/II study of MGCD0103, an oral isotype-selective histone deacetylase (HDAC) inhibitor, in combination with 5-azacitidine in higher-risk myelodysplastic syndrome (MDS) and acute myelogenous leukemia (AML). Blood 2007;110:137a.
  • Undevia SD, Kindler HL, Janisch L, et al. A phase I study of the oral combination of CI-994, a putative histone deacetylase inhibitor, and capecitabine. Ann Oncol 2004;15:1705–11.
  • Pauer LR, Olivares J, Cunningham C, et al. Phase I study of oral CI-994 in combination with carboplatin and paclitaxel in the treatment of patients with advanced solid tumors. Cancer Invest 2004;22:886–96.
  • Nemunaitis JJ, Orr D, Eager R, et al. Phase I study of oral CI-994 in combination with gemcitabine in treatment of patients with advanced cancer. Cancer J 2003;9:58–66.
  • Prakash S, Foster BJ, Meyer M, et al. Chronic oral administration of CI-994: a phase 1 study. Invest New Drugs 2001;19:1–11.
  • Verna L, Whysner J, Williams GM. 2-acetylaminofluorene mechanistic data and risk assessment: DNA reactivity, enhanced cell proliferation and tumor initiation. Pharmacol Ther 1996;71:83–105.
  • Wagner JM, Hackanson B, Lubbert M, Jung M. Histone deacetylase (HDAC) inhibitors in recent clinical trials for cancer therapy. Clin Epigenetics 2010;1:117–36.
  • Krauze AV, Myrehaug SD, Chang MG, et al. A phase 2 study of concurrent radiation therapy, temozolomide, and the histone deacetylase inhibitor valproic acid for patients with glioblastoma. Int J Radiat Oncol 2015;92:986–92.
  • Kuendgen A, Strupp C, Hildebrandt B, et al. Phase 2 trial of the histone deacetylase inhibitor valproic acid as a monotherapy or in combination with all-trans retinoic acid in 24 patients with acute myeloid leukemia. Blood 2004;104:501a.
  • Aviram A, Zimrah Y, Shaklai M, et al. Comparison between the effect of butyric-acid and its prodrug pivaloyloxymethylbutyrate on histones hyperacetylation in an Hl-60 leukemic-cell line. Int J Cancer 1994;56:906–9.
  • Gore SD, Weng LJ, Yu K, Fu S. Phenylbutyrate in myeloid malignancies: relationship between inhibition of histone deacetylase, cytostasis and differentiation. Clin Cancer Res 1999;5:3817s.
  • Suzuki T, Kouketsu A, Matsuura A, et al. Thiol-based SAHA analogues as potent histone deacetylase inhibitors. Bioorg Med Chem Lett 2004;14:3313–17.
  • Nishino N, Jose B, Okamura S, et al. Cyclic tetrapeptides bearing a sulfhydryl group potently inhibit histone deacetylases. Org Lett 2003;5:5079–82.
  • Wen JC, Niu Q, Liu J, et al. Novel thiol-based histone deacetylase inhibitors bearing 3-phenyl-1H-pyrazole-5-carboxamide scaffold as surface recognition motif: design, synthesis and SAR study. Bioorg Med Chem Lett 2016;26:375–9.
  • Suzuki T, Kouketsu A, Itoh Y, et al. Highly potent and selective histone deacetylase 6 inhibitors designed based on a small-molecular substrate. J Med Chem 2006;49:4809–12.
  • Giannini G, Vesci L, Battistuzzi G, et al. ST7612AA1, a thioacetate-omega(gamma-lactam carboxamide) derivative selected from a novel feneration of oral HDAC inhibitors. J Med Chem 2014;57:8358–77.
  • Vesci L, Bernasconi E, Milazzo FM, et al. Preclinical antitumor activity of ST7612AA1: a new oral thiol-based histone deacetylase (HDAC) inhibitor. Oncotarget 2015;6:5735–48.
  • Battistuzzi G, Giannini G. Synthesis of ST7612AA1, a novel oral HDAC inhibitor, via radical thioacetic acid addition. Curr Bioact Compd 2016;12:282–8.
  • Hu ED, Dul E, Sung CM, et al. Identification of novel isoform-selective inhibitors within class I histone deacetylases. J Pharmacol Exp Ther 2003;307:720–8.
  • Kleinschek A, Meyners C, Digiorgio E, et al. Non-hydroxamate histone deacetylase 8 inhibitors. ChemMedChem 2016;11:2598–606.
  • Ononye SN, VanHeyst MD, Oblak EZ, et al. Tropolones as lead-like natural products: the development of potent and selective histone deacetylase inhibitors. Acs Med Chem Lett 2013;4:757–61.
  • Patil V, Sodji QH, Kornacki JR, et al. 3-Hydroxypyridin-2-thione as novel zinc binding group for selective histone deacetylase inhibition. J Med Chem 2013;56:3492–506.
  • Attenni B, Ontoria JM, Cruz JC, et al. Histone deacetylase inhibitors with a primary amide zinc binding group display antitumor activity in xenograft model. Bioorg Med Chem Lett 2009;19:3081–4.
  • Valente S, Conte M, Tardugno M, et al. Developing novel non-hydroxamate histone deacetylase inhibitors: the chelidamic warhead. MedChemComm 2012;3:298–304.
  • Wang YF, Stowe RL, Pinello CE, et al. Identification of histone deacetylase inhibitors with benzoylhydrazide scaffold that selectively inhibit class I histone deacetylases. Chem Biol 2015;22:273–84.
  • McClure J, Zhang C, Inks E, et al. Development of allosteric hydrazide-containing class I histone deacetylase inhibitors for use in acute myeloid leukemia. J Med Chem 2016;59:9942–59.
  • Lobera M, Madauss KP, Pohlhaus DT, et al. Selective class IIa histone deacetylase inhibition via a nonchelating zinc-binding group. Nat Chem Biol 2013;9:319–25.
  • Li YX, Woster PM. Discovery of a new class of histone deacetylase inhibitors with a novel zinc binding group. MedChemComm 2015;6:613–18.
  • Kemp MM, Wang Q, Fuller JH, et al. A novel HDAC inhibitor with a hydroxy-pyrimidine scaffold. Bioorg Med Chem Lett 2011;21:4164–9.
  • Park H, Kim S, Kim YE, Lima SJ. A structure-based virtual screening approach toward the discovery of histone deacetylase inhibitors: identification of promising zinc-chelating groups. ChemMedChem 2010;5:591–7.
  • Musso L, Cincinelli R, Zuco V, et al. Investigation on the ZBG-functionality of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase inhibitors. Bioorg Med Chem Lett 2015;25:4457–60.
  • Zhou JW, Li M, Chen NH, et al. Computational design of a time-dependent histone deacetylase 2 selective inhibitor. Acs Chem Biol 2015;10:687–92.
  • Chakrabarti A, Oehme I, Witt O, et al. HDAC8: a multifaceted target for therapeutic interventions. Trends Pharmacol Sci 2015;36:481–92.
  • Mann BS, Johnson JR, Cohen MH, et al. FDA approval summary: vorinostat for treatment of advanced primary cutaneous T-cell lymphoma. Oncologist 2007;12:1247–52.