| Identification | Back Directory | [Name]
PTACH | [CAS]
848354-66-5 | [Synonyms]
NCH 51
NCH51, >98%
PTACH?, >98%
PTACH (NCH-51)
HDAC Inhibitor XXII, NCH51
HDAC Inhibitor XXII, NCH51 - CAS 848354-66-5 - Calbiochem
Cpd 51, S-[6-(4-Phenyl-2-thiazolylcarbamoyl)hexyl] thioisobutyrate
S-(7-Oxo-7-((4-phenylthiazol-2-yl)amino)-heptyl) 2-methylpropanethioate
2-MethylpropanethioicacidS-[7-oxo-7-[(4-phenyl-2-thiazolyl)amino]heptyl]ester
Propanethioic acid,2-methyl-, S-[7-oxo-7-[(4-phenyl-2-thiazolyl)amino]heptyl] ester | [Molecular Formula]
C20H26N2O2S2 | [MDL Number]
MFCD08705329 | [MOL File]
848354-66-5.mol | [Molecular Weight]
390.56 |
| Chemical Properties | Back Directory | [Melting point ]
127-128 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6)) | [density ]
1.181±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble26mg/mL | [form ]
White powder | [pka]
9.52±0.50(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
NCH 51 is a Histone deacetylase inhibitor. | [Definition]
ChEBI: 2-methylpropanethioic acid S-[7-oxo-7-[(4-phenyl-2-thiazolyl)amino]heptyl] ester is an aromatic amide. | [General Description]
A cell-permeable S-isobutyryl prodrug that is processed intracellularly to form the potent HDAC inhibitor NCH-31 (IC50 = 48 and 170 nM, respectively, using partially purified HDAC1 or HeLa nuclear extract) that is predicted to exhibit a similar HADC binding mode as that of SAHA with its sulfhydryl replacing SAHA′s hydroxamate as the active-site zinc-targeting group. NCH-51 is shown to exhibit comparable antiproliferative (mean IC50 = 3.8 μM vs. 3.7 μM for SAHA; 48 h treatment) and apoptotic activity as SAHA against various cancer cell lines, but not PBMCs from 4 healthy individuals (IC50 >30 μM with either drug), and the antioxidant N-Acetyl-L-Cysteine (NAC; Cat. No. 106425) at 2 mM is reported to abolish the cell-growth inhibition caused by either 3 μM NCH-51 or SAHA in the Multiple Myeloma U266 cultures. Half-life in human plasma at 37 °C = 24 h. | [Biological Activity]
Histone deacetylase (HDAC) inhibitor. Inhibits growth of various cancer cells in vitro (EC 50 = 1.1-9.1 μ M). | [Biochem/physiol Actions]
HDAC inhibitor; more potent than the majority of HDAC inhibitors except for SAHA (gold standard). | [References]
[1]. suzuki t, hisakawa s, itoh y, et al. identification of a potent and stable antiproliferative agent by the prodrug formation of a thiolate histone deacetylase inhibitor. bioorg med chem lett, 2007, 17(6): 1558-1561.
[2]. suzuki t, nagano y, kouketsu a, et al. novel inhibitors of human histone deacetylases: design, synthesis, enzyme inhibition, and cancer cell growth inhibition of saha-based non-hydroxamates. j med chem, 2005, 48(4): 1019-1032.
[3]. sanda t, okamoto t, uchida y, et al. proteome analyses of the growth inhibitory effects of nch-51, a novel histone deacetylase inhibitor, on lymphoid malignant cells. leukemia, 2007, 21(11): 2344-2353.
[4]. victoriano af, imai k, togami h, et al. novel histone deacetylase inhibitor nch-51 activates latent hiv-1 gene expression. febs lett, 2011, 585(7): 1103-1111. |
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