PTACH Chemical Properties

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

InChI

1S/C20H26N2O2S2/c1-15(2)19(24)25-13-9-4-3-8-12-18(23)22-20-21-17(14-26-20)16-10-6-5-7-11-16/h5-7,10-11,14-15H,3-4,8-9,12-13H2,1-2H3,(H,21,22,23)

InChIKey

MDYDGUOQFUQOGE-UHFFFAOYSA-N

SMILES

CC(C)C(=O)SCCCCCCC(=O)Nc1nc(cs1)-c2ccccc2

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

WGK Germany 

3

Storage Class

11 - Combustible Solids

PTACH Usage And Synthesis

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.

PTACH(848354-66-5)Related Product Information

• PTACH