Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.5.1.98 extracted from

  • Wagner, F.F.; Weiwer, M.; Steinbacher, S.; Schomburg, A.; Reinemer, P.; Gale, J.P.; Campbell, A.J.; Fisher, S.L.; Zhao, W.N.; Reis, S.A.; Hennig, K.M.; Thomas, M.; Mueller, P.; Jefson, M.R.; Fass, D.M.; Haggarty, S.J.; Zhang, Y.L.; Holson, E.B.
    Kinetic and structural insights into the binding of histone deacetylase 1 and 2 (HDAC1, 2) inhibitors (2016), Bioorg. Med. Chem., 24, 4008-4015 .
    View publication on PubMed
Search for more literature for 3.5.1.98

Inhibitors

Inhibitors Comment Organism Structure
(1R,5S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-6-oxabicyclo[3.1.1]heptane-3-carboxamide i.e. BRD7232, inhibition kinetics; i.e. BRD7232, possesses kinetic selectivity for isozyme HDAC1 versus HDAC2, inhibition kinetics; inhibition kinetics Homo sapiens
(2R)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-2-carboxamide
-
 Homo sapiens
(2S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-2-carboxamide
-
 Homo sapiens
additional information determination of structure-activity and structure-kinetic relationships of a series of selective ortho-aminoanilide inhibitors of histone deacetylase isozymes (HDACs) 1 and 2, overview. Measurements of increases in neuronal histone acetylation in mouse fore-brain primary neuronal cultures induced by HDAC inhibitor compounds. Analysis of the stability of the compounds in murine plasma and liver microsomes; determination of structure-activity and structure-kinetic relationships of a series of selective ortho-aminoanilide inhibitors of histone deacetylase isozymes (HDACs) 1 and 2, overview. Measurements of increases in neuronal histone acetylation in mouse fore-brain primary neuronal cultures induced by HDAC inhibitor compounds. Analysis of the stability of the compounds in murine plasma and liver microsomes; determination of structure-activity and structure-kinetic relationships of a series of selective ortho-aminoanilide inhibitors of histone deacetylase isozymes (HDACs) 1 and 2, overview. Measurements of increases in neuronal histone acetylation in mouse fore-brain primary neuronal cultures induced by HDAC inhibitor compounds. Analysis of the stability of the compounds in murine plasma and liver microsomes Homo sapiens
N-(4-amino-3'-fluoro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
-
 Homo sapiens
N-(4-amino-4'-chloro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
-
 Homo sapiens
N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3,4-dihydro-1H-2-benzopyran-3-carboxamide
-
 Homo sapiens
N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3,4-dihydro-2H-1-benzopyran-3-carboxamide
-
 Homo sapiens
N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3-oxabicyclo[3.1.0]hexane-6-carboxamide
-
 Homo sapiens
N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-3-carboxamide
-
 Homo sapiens
N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide i.e. BRD4884, coordinates to the Zn2+ ion via the free aniline -NH2, completing its tetrahedral coordination sphere in addition to the side chains of Asp181, His183, and Asp269 with the anilide carbonyl oxygen situated at a distance of 2.8 A to the Zn2+ ion. The anilide-NH of BRD4884 forms an H-bond to the backbone carbonyl oxygen of Gly154. The 11 A lipophilic channel harbors the tetrahydropyran moiety of BRD4884 making Van Der Waals contacts with the channel wall. The tetrahydropyran ring adopts a preferential chair conformation allowing the pyran oxygen atom to form a hydrogen bond (3.5 A) with a conserved water at the surface of HDAC2, inhibition kinetics; i.e. BRD4884, possesses kinetic selectivity for isozyme HDAC1 versus HDAC2, inhibition kinetics; inhibition kinetics Homo sapiens
N-(4-amino[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
-
 Homo sapiens
N-[2-amino-5-(pyridin-3-yl)phenyl]oxane-4-carboxamide
-
 Homo sapiens
N-[2-amino-5-(pyridin-4-yl)phenyl]oxane-4-carboxamide
-
 Homo sapiens
N-[4-amino-4'-(trifluoromethyl)[1,1'-biphenyl]-3-yl]oxane-4-carboxamide
-
 Homo sapiens

Metals/Ions

Metals/Ions Comment Organism Structure
Zn2+ bound in the catalytic pocket Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens O15379
-
-
Homo sapiens Q13547
-
-
Homo sapiens Q92769
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information enzyme assay using carboxyfluorescein (FAM)-labeled acetylated or trifluoroacetylated peptide substrates in vitro, and in a cell-based assay by measuring H3K9 and H4K12 acetylation changes in primary mouse neuronal culture Homo sapiens ?
-
-

Synonyms

Synonyms Comment Organism
HDAC1
-
 Homo sapiens
HDAC2
-
 Homo sapiens
HDAC3
-
 Homo sapiens
histone deacetylase 1
-
 Homo sapiens
histone deacetylase 2
-
 Homo sapiens
histone deacetylase 3
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
22
-
 assay at room temperature Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
 assay at Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00002
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.000045
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3,4-dihydro-1H-2-benzopyran-3-carboxamide
0.000062
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.000072
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3,4-dihydro-2H-1-benzopyran-3-carboxamide
0.000119
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-(4-amino[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.000119
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3,4-dihydro-1H-2-benzopyran-3-carboxamide
0.000123
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3-oxabicyclo[3.1.0]hexane-6-carboxamide
0.000156
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3,4-dihydro-2H-1-benzopyran-3-carboxamide
0.000168
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens (1R,5S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-6-oxabicyclo[3.1.1]heptane-3-carboxamide
0.000192
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens (1R,5S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-6-oxabicyclo[3.1.1]heptane-3-carboxamide
0.000219
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3-oxabicyclo[3.1.0]hexane-6-carboxamide
0.000312
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-(4-amino[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.000467
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens (2R)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-2-carboxamide
0.00109
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.00122
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-3-carboxamide
0.00129
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens (2R)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-2-carboxamide
0.00142
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-[2-amino-5-(pyridin-4-yl)phenyl]oxane-4-carboxamide
0.00143
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens (2S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-2-carboxamide
0.00145
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens (1R,5S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-6-oxabicyclo[3.1.1]heptane-3-carboxamide
0.00145
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens (2S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-2-carboxamide
0.00149
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3-oxabicyclo[3.1.0]hexane-6-carboxamide
0.00152
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-(4-amino-4'-chloro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.00159
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens (1R,5S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-6-oxabicyclo[3.1.1]heptane-3-carboxamide
0.00228
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens (1R,5S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-6-oxabicyclo[3.1.1]heptane-3-carboxamide
0.00235
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-[2-amino-5-(pyridin-4-yl)phenyl]oxane-4-carboxamide
0.00253
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-(4-amino-4'-chloro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.00385
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens N-(4-amino[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.00473
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-3-carboxamide
0.00559
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-3-carboxamide
0.00573
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens (2R)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-2-carboxamide
0.00595
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens (2S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-2-carboxamide
0.00626
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-3-carboxamide
0.00645
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-[2-amino-5-(pyridin-3-yl)phenyl]oxane-4-carboxamide
0.00656
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-3-carboxamide
0.00732
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-[2-amino-5-(pyridin-3-yl)phenyl]oxane-4-carboxamide
0.00967
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-(4-amino-3'-fluoro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.0123
-
 pH 7.4, 22°C, HDAC2 isozyme Homo sapiens N-(4-amino-3'-fluoro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.0137
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens (1R,5S)-N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-6-oxabicyclo[3.1.1]heptane-3-carboxamide
0.0142
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens N-(4-amino-4'-chloro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.0198
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)oxane-3-carboxamide
0.0208
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens N-[2-amino-5-(pyridin-3-yl)phenyl]oxane-4-carboxamide
0.0259
-
 pH 7.4, 22°C, HDAC3 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3,4-dihydro-1H-2-benzopyran-3-carboxamide
0.0267
-
 pH 7.4, 22°C, HDAC1 isozyme Homo sapiens N-[4-amino-4'-(trifluoromethyl)[1,1'-biphenyl]-3-yl]oxane-4-carboxamide
0.033
-
 pH 7.4, 22°C, above, HDAC2 isozyme Homo sapiens N-[4-amino-4'-(trifluoromethyl)[1,1'-biphenyl]-3-yl]oxane-4-carboxamide
0.033
-
 pH 7.4, 22°C, above, HDAC3 isozyme Homo sapiens N-(4-amino-3'-fluoro[1,1'-biphenyl]-3-yl)oxane-4-carboxamide
0.033
-
 pH 7.4, 22°C, above, HDAC3 isozyme Homo sapiens N-(4-amino-4'-fluoro[1,1'-biphenyl]-3-yl)-3,4-dihydro-2H-1-benzopyran-3-carboxamide
0.033
-
 pH 7.4, 22°C, above, HDAC3 isozyme Homo sapiens N-[2-amino-5-(pyridin-4-yl)phenyl]oxane-4-carboxamide
0.033
-
 pH 7.4, 22°C, above, HDAC3 isozyme Homo sapiens N-[4-amino-4'-(trifluoromethyl)[1,1'-biphenyl]-3-yl]oxane-4-carboxamide