69. Almaliti J, Al-Hamashi AA, Negmeldin AT et al (2016) Largazole analogues embodying
radical changes in the depsipeptide ring: development of a more selective and highly potent
analogue. J Med Chem 59:10642–10660
70. Kitir B, Maolanon AR, Ohm RG et al (2017) Chemical editing of macrocyclic natural products
and kinetic profiling reveal slow, tight-binding histone deacetylase inhibitors with picomolar
affinities. Biochemistry 56:5134–5146
71. Gu W, Nusinzon I, Smith RD Jr et al (2006) Carbonyl- and sulfur-containing analogs of
suberoylanilide hydroxamic acid: potent inhibition of histone deacetylases. Bioorg Med Chem
14:3320–3329
72. Saito A, Yamashita T, Mariko Y et al (1999) A synthetic inhibitor of histone deacetylase,
MS-27-275, with marked in vivo antitumor activity against human tumors. Proc Natl Acad Sci
U S A 96:4592–4597
73. Fournel M, Bonfils C, Hou Y et al (2008) MGCD0103, a novel isotype-selective histone
deacetylase inhibitor, has broad spectrum antitumor activity in vitro and in vivo. Mol Cancer
Ther 7:759–768
74. Lu XP, Ning ZQ, Li ZB et al (2016) Discovery and development of HDAC subtype selective
inhibitor chidamide: potential immunomodulatory activity against cancers. In: Fischer J,
Childers WE (eds) Successful drug discovery, vol 2. Wiley-VCH, Weinheim, pp 89–114
75. Ning ZQ, Li ZB, Newman MJ et al (2012) Chidamide (CS055/HBI-8000): a new histone
deacetylase inhibitor of the benzamide class with antitumor activity and the ability to enhance
immune cell-mediated tumor cell cytotoxicity. Cancer Chemother Pharmacol 69:901–909
76. Witter DJ, Harrington P, Wilson KJ et al (2008) Optimization of biaryl selective HDAC1&2
inhibitors (SHI-1:2). Bioorg Med Chem Lett 18:726–731
77. McClure JJ, Inks ES, Zhang C et al (2017) Comparison of the deacylase and deacetylase
activity of zinc-dependent HDACs. ACS Chem Biol 12:1644–1655
78. Candido EP, Reeves R, Davie JR (1978) Sodium butyrate inhibits histone deacetylation in
cultured cells. Cell 14:105–113
79. Kim SW, Hooker JM, Otto N et al (2013) Whole-body pharmacokinetics of HDAC inhibitor
drugs, butyric acid, valproic acid and 4-phenylbutyric acid measured with carbon-11 labeled
analogs by PET. Nucl Med Biol 40:912–918
80. Wen S, Carey KL, Nakao Y et al (2007) Total synthesis of azumamide A and azumamide E,
evaluation as histone deacetylase inhibitors, and design of a more potent analogue. Org Lett
9:1105–1108
81. Porter NJ, Christianson DW (2017) Binding of the microbial cyclic tetrapeptide trapoxin A to
the class I histone deacetylase HDAC8. ACS Chem Biol 12:2281–2286
82. Olsen CA, Montero A, Leman LJ et al (2012) Macrocyclic peptoidÀpeptide hybrids as
inhibitors of class I histone deacetylases. ACS Med Chem Lett 3:749–753
83. Islam MN, Islam MS, Hoque MA et al (2014) Bicyclic tetrapeptides as potent HDAC
inhibitors: effect of aliphatic loop position and hydrophobicity on inhibitory activity. Bioorg
Med Chem 22:3862–3870
84. Traoré MDM, Zwick V, Simões-Pires CA et al (2017) Hydroxyl ketone-based histone
deacetylase inhibitors to gain insight into class I HDAC selectivity versus that of HDAC6.
ACS Omega 2:1550–1562
85. Whitehead L, Dobler MR, Radetich B et al (2011) Human HDAC isoform selectivity achieved
via exploitation of the acetate release channel with structurally unique small molecule inhibitors. Bioorg Med Chem 19:4626–4634
86. Lobera M, Madauss KP, Pohlhaus DT et al (2013) Selective class IIa histone deacetylase
inhibition via a nonchelating zinc-binding group. Nat Chem Biol 9:319–325
87. Attenni B, Ontoria JM, Cruz JC et al (2009) Histone deacetylase inhibitors with a primary
amide zinc binding group display antitumor activity in xenograft model. Bioorg Med Chem
Lett 19:3081–3084
Targeting the Zinc-Dependent Histone Deacetylases (HDACs) for Drug Discovery
25
radical changes in the depsipeptide ring: development of a more selective and highly potent
analogue. J Med Chem 59:10642–10660
70. Kitir B, Maolanon AR, Ohm RG et al (2017) Chemical editing of macrocyclic natural products
and kinetic profiling reveal slow, tight-binding histone deacetylase inhibitors with picomolar
affinities. Biochemistry 56:5134–5146
71. Gu W, Nusinzon I, Smith RD Jr et al (2006) Carbonyl- and sulfur-containing analogs of
suberoylanilide hydroxamic acid: potent inhibition of histone deacetylases. Bioorg Med Chem
14:3320–3329
72. Saito A, Yamashita T, Mariko Y et al (1999) A synthetic inhibitor of histone deacetylase,
MS-27-275, with marked in vivo antitumor activity against human tumors. Proc Natl Acad Sci
U S A 96:4592–4597
73. Fournel M, Bonfils C, Hou Y et al (2008) MGCD0103, a novel isotype-selective histone
deacetylase inhibitor, has broad spectrum antitumor activity in vitro and in vivo. Mol Cancer
Ther 7:759–768
74. Lu XP, Ning ZQ, Li ZB et al (2016) Discovery and development of HDAC subtype selective
inhibitor chidamide: potential immunomodulatory activity against cancers. In: Fischer J,
Childers WE (eds) Successful drug discovery, vol 2. Wiley-VCH, Weinheim, pp 89–114
75. Ning ZQ, Li ZB, Newman MJ et al (2012) Chidamide (CS055/HBI-8000): a new histone
deacetylase inhibitor of the benzamide class with antitumor activity and the ability to enhance
immune cell-mediated tumor cell cytotoxicity. Cancer Chemother Pharmacol 69:901–909
76. Witter DJ, Harrington P, Wilson KJ et al (2008) Optimization of biaryl selective HDAC1&2
inhibitors (SHI-1:2). Bioorg Med Chem Lett 18:726–731
77. McClure JJ, Inks ES, Zhang C et al (2017) Comparison of the deacylase and deacetylase
activity of zinc-dependent HDACs. ACS Chem Biol 12:1644–1655
78. Candido EP, Reeves R, Davie JR (1978) Sodium butyrate inhibits histone deacetylation in
cultured cells. Cell 14:105–113
79. Kim SW, Hooker JM, Otto N et al (2013) Whole-body pharmacokinetics of HDAC inhibitor
drugs, butyric acid, valproic acid and 4-phenylbutyric acid measured with carbon-11 labeled
analogs by PET. Nucl Med Biol 40:912–918
80. Wen S, Carey KL, Nakao Y et al (2007) Total synthesis of azumamide A and azumamide E,
evaluation as histone deacetylase inhibitors, and design of a more potent analogue. Org Lett
9:1105–1108
81. Porter NJ, Christianson DW (2017) Binding of the microbial cyclic tetrapeptide trapoxin A to
the class I histone deacetylase HDAC8. ACS Chem Biol 12:2281–2286
82. Olsen CA, Montero A, Leman LJ et al (2012) Macrocyclic peptoidÀpeptide hybrids as
inhibitors of class I histone deacetylases. ACS Med Chem Lett 3:749–753
83. Islam MN, Islam MS, Hoque MA et al (2014) Bicyclic tetrapeptides as potent HDAC
inhibitors: effect of aliphatic loop position and hydrophobicity on inhibitory activity. Bioorg
Med Chem 22:3862–3870
84. Traoré MDM, Zwick V, Simões-Pires CA et al (2017) Hydroxyl ketone-based histone
deacetylase inhibitors to gain insight into class I HDAC selectivity versus that of HDAC6.
ACS Omega 2:1550–1562
85. Whitehead L, Dobler MR, Radetich B et al (2011) Human HDAC isoform selectivity achieved
via exploitation of the acetate release channel with structurally unique small molecule inhibitors. Bioorg Med Chem 19:4626–4634
86. Lobera M, Madauss KP, Pohlhaus DT et al (2013) Selective class IIa histone deacetylase
inhibition via a nonchelating zinc-binding group. Nat Chem Biol 9:319–325
87. Attenni B, Ontoria JM, Cruz JC et al (2009) Histone deacetylase inhibitors with a primary
amide zinc binding group display antitumor activity in xenograft model. Bioorg Med Chem
Lett 19:3081–3084
Targeting the Zinc-Dependent Histone Deacetylases (HDACs) for Drug Discovery
25