382185

HDAC Inhibitor XXII, NCH51

The HDAC Inhibitor XXII, NCH51, also referenced under CAS 848354-66-5, controls the biological activity of HDAC. This small molecule/inhibitor is primarily used for Cell Structure applications.

• Synonym(s): HDAC Inhibitor XXII, NCH51, Thioisobutyric acid(S-(6-(4-phenyl-2-thiazolylcarbamoyl)hexyl) ester
• Empirical Formula (Hill Notation): C₂₀H₂₆N₂O₂S₂
• CAS Number: 848354-66-5
• Molecular Weight: 390.56
• MDL number: MFCD08705329
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• assay: ≥97% (HPLC)
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: DMSO: 100 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• 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)
• InChI key: MDYDGUOQFUQOGE-UHFFFAOYSA-N

Description

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.

Warning

Toxicity: Regulatory Review (Z)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

#31: Thiol - 7-Mercaptoheptanoic acid (4-phenyl-2-thiazolyl)amide

Sanda, T., et al. 2007. Leukemia21, 2344.
Suzuki, T., et al. 2007. Bioorg. Med. Chem. Lett.17, 1558.
Suzuki, T., et al. 2005. J. Med. Chem.48, 1019.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable