Cat. No. Name Size Price Add Cart
KI0254MC156810 mg$192
MC156825 mg$432

Chemical Characteristic

Product NameMC1568
CAS No.852475-26-4
Molecular Weight 314.31
FormulaC17H15FN2O3
Chemical Name3-[4-[3-(3-Fluorophenyl)-3-oxo-1-propenyl]-1-methyl-1H-pyrrol-2-yl]-N-hydroxy-2-propenamide
SmilesC(=O)(/C=C/c1n(cc(c1)/C=C/C(=O)c1cc(ccc1)F)C)NO
Chemical Structure

Biological activities

MC1568 is a selective class II (IIa) histone deacetylas (HDAC II) inhibitor. MC1568 inhibits HDAC II with an IC50 of 220 nM and shows 176-fold class II selectivity against class I. MC1568 arrests myogenesis by decreasing myocyte enhancer factor 2D (MEF2D) expression, by stabilizing the HDAC4??DAC3??EF2D complex, and by inhibiting differentiation-induced MEF2D acetylation. [1] At the cellular level, MC1568 inhibits HDAC6 in both breast (ZR75.1) and haematological (U937) cancer cells, as revealed by hyper-acetylation of α-tubulin. MC1568 blocks the class II HDAC enzymatic activity, concomitantly stabilizing the interaction of MEF2 with the HDAC4??COR??DAC3 complex, without altering HDAC4 acetylation levels. In vitro, MC1568 blocks the induction of myogenin and α-myosin heavy chain (αMHC) gene expression 48 hours after the addition of differentiation medium. MC1568 inhibits the acetylation of MEF2D immunoprecipitation and blocks the concomitant release of co-precipitated HDAC4. The inhibition of MC1568 for histone H3 acetylation at the MEF2D target gene myogenin promoter is revealed by quantitative PCR chromatin immunoprecipitation. Meanwhile, MC1568 induces cell cycle arrest, showing accumulation of cells in the G2/M phase of the cell cycle for TSA, and in the G1 phase. [2] MC1568 inhibits MCF-7 and MDA-MB 231 cell proliferation in a dose-dependent manner and induces different effects on cell cycle and cyclin D1 expression. [3] In vivo, after a 6 hours acute administration of MC1568, tubulin acetylation increases in organs such as the kidney, spleen, muscle and heart. In the presence of MC1568, the MEF2D complex also retains class I HDAC-dependent deacetylase activity. In skeletal muscle and heart, MC1568 inhibits the activity of HDAC4 and HDAC5 without affecting HDAC3 activity. [2]

Protocols

MC1568 is dissolved in DMSO and stored at -20°C before use. [1]

References

[1] Mai A, et al. Class II (IIa)-selective histone deacetylase inhibitors. 1. Synthesis and biological evaluation of novel (aryloxopropenyl) pyrrolyl hydroxyamides. J Med Chem. 2005, 48(9): 3344-3353.
[2] Nebbioso A, et al. Selective class II HDAC inhibitors impair myogenesis by modulating the stability and activity of HDAC??EF2 complexes. EMBO Rep. 2009, 10(7): 776-782.
[3] Duong V, et al. Specific activity of class II histone deacetylases in human breast cancer cells. Mol Cancer Res. 2008, 6(12): 1908-1919.

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