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MC1568Class II HDAC inhibitor,potent and

MC1568

Catalog No. A4094
Size Price Stock Qty
10mM (in 1mL DMSO) $55.00 In stock
Evaluation Sample $28.00 In stock
10mg $50.00 In stock
25mg $100.00 In stock

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Sample solution is provided at 25 µL, 10mM.

Product Citations

1. Ha, Soon-Duck, et al. "Inhibition of IL-1β Expression by Anthrax Lethal Toxin is Reversed by HDAC8 Inhibition in Murine Macrophages." Journal of Biological Chemistry (2016): jbc-M115. PMID:26912657

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Chemical structure

MC1568

Related Biological Data

MC1568

Related Biological Data

MC1568

Biological Activity

Description MC1568 is a selective inhibitor of HDAC for maize HD1-A with IC50 of 100 nM. It is 34-fold more selective for HD1-A than HD1-B.
Targets HD1-A (Maize) HD1-B (Maize)        
IC50 100 nM 3400 nM        

Protocol

Kinase experiment [1]:

Maize HD2, HD1-B, and HD1-A enzyme inhibition

The enzyme liberated tritiated acetic acid from the substrate, which was quantified by scintillation counting. IC50 values are results of triple determinations. A 50 μL sample of maize enzyme (at 30 °C) was incubated (30 mins) with 10 μL of total [3H]acetate-prelabeled chicken reticulocyte histones (2 mg/mL). Reaction was stopped by addition of 50 μL of 1 M HCl/0.4 M acetate and 800 μL of ethyl acetate. After centrifugation (10000 g, 5 mins), an aliquot of 600 μL of the upper phase was counted for radioactivity in 3 mL of liquid scintillation cocktail. MC1568 was tested at a starting concentration of 40 μM, and active substances were diluted further. NaB, VPA, TSA, SAHA, 85TPX, HC-toxin, and tubacin were used as the reference compounds, and blank solvents were used as negative controls.

Cell experiment [2]:

Cell lines

3T3-L1 cells

Preparation method

The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20 °C for several months.

Reaction Conditions

~ 10 μM; 8 days

Applications

In 3T3-L1 cells, MC1568 attenuated PPARγ-induced adipogenesis.

Animal experiment [2]:

Animal models

PPRE-Luc transgenic C57BL/6 mice

Dosage form

50 mg/kg; p.o.; q.d., for 7 days

Applications

In PPRE-Luc transgenic C57BL/6 mice, MC1568 (50 mg/kg) impaired PPARγ signaling mostly in the heart and adipose tissues.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Mai A, Massa S, Pezzi R, Simeoni S, Rotili D, Nebbioso A, Scognamiglio A, Altucci L, Loidl P, Brosch G. Class II (IIa)-selective histone deacetylase inhibitors. 1. Synthesis and biological evaluation of novel (aryloxopropenyl)pyrrolyl hydroxyamides. J Med Chem. 2005 May 5;48(9):3344-53.

[2]. Nebbioso A, Dell'Aversana C, Bugge A, Sarno R, Valente S, Rotili D, Manzo F, Teti D, Mandrup S, Ciana P, Maggi A, Mai A, Gronemeyer H, Altucci L. HDACs class II-selective inhibition alters nuclear receptor-dependent differentiation. J Mol Endocrinol. 2010 Oct;45(4):219-28.

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Chemical Properties

Cas No. 852475-26-4 SDF Download SDF
Synonyms MC 1568, MC-1568
Chemical Name (E)-3-[4-[(E)-3-(3-fluorophenyl)-3-oxoprop-1-enyl]-1-methylpyrrol-2-yl]-N-hydroxyprop-2-enamide
Canonical SMILES CN1C=C(C=C1C=CC(=O)NO)C=CC(=O)C2=CC(=CC=C2)F
Formula C17H15FN2O3 M.Wt 314.31
Solubility Soluble in DMSO > 10 mM Storage Store at -20°C
General tips No
Shipping Condition No

Research Update

1. Class II-specific histone deacetylase inhibitors MC1568 and MC1575 suppress IL-8 expression in human melanoma cells. Pigment Cell Melanoma Res. 2013 Mar;26(2):193-204. doi: 10.1111/pcmr.12049. Epub 2013 Jan 7.
Abstract
MC1568, an HDACi, inhibited IL-8 levels and cell proliferation in unstimulated or PMA-stimulated GR-M and OCM-3 melanoma cell lines through suppressing c-Jun binding to the IL-8 promoter, recruitment of histones 3&4, Rna polymerase II and TFIIB to the IL-8 promoter and c-Jun expression.
2. Improved Synthesis and Structural Reassignment of MC1568: A Class IIa Selective HDAC Inhibitor. J Med Chem. 2014 Feb 13;57(3):1132-5. doi: 10.1021/jm401945k. Epub 2014 Jan 30.
Abstract
MC1568, an inhibitor of class IIa HDAC has been described in terms of synthesis and structural reassignment.

Background

MC1568, a derivative of (Aryloxopropenyl)pyrrolyl hydroxyamide, is a novel, potent and specific inhibitor of class II histone deacetylase (HDAC), including two subclasses IIa (HDAC4, HDAC5, HDAC6, HDAC7 and HDAC9) and IIb (HDAC6 and HDAC 10), that exhibits strong inhibition against maize class II HDAC with 50% inhibition concentration IC50 value of 22 μM. MC1568 has been found to tissue-selectively inhibits HDAC and arrest myogenesis in cultured muscle cells through three possible mechanisms, including decreasing the expression of myocyte enhancer factor 2D, stabilizing the HDAC-HDAC3-MEF2D complex and inhibiting the acetylation of differentiation-induced MEF2D. Moreover, MC1568 is able to interfere with RAR- and PPARγ-mediated differentiation-inducing signaling pathways.

Reference

Mai A, Massa S, Pezzi R, Simeoni S, Rotili D, Nebbioso A, Scognamiglio A, Altucci L, Loidl P, Brosch G. Class II (IIa)-selective histone deacetylase inhibitors. 1. Synthesis and biological evaluation of novel (aryloxopropenyl)pyrrolyl hydroxyamides. J Med Chem. 2005 May 5;48(9):3344-53.

Nebbioso A, Dell'Aversana C, Bugge A, Sarno R, Valente S, Rotili D, Manzo F, Teti D, Mandrup S, Ciana P, Maggi A, Mai A, Gronemeyer H, Altucci L. HDACs class II-selective inhibition alters nuclear receptor-dependent differentiation. J Mol Endocrinol. 2010 Oct;45(4):219-28. doi: 10.1677/JME-10-0043. Epub 2010 Jul 16.

Nebbioso A, Manzo F, Miceli M, Conte M, Manente L, Baldi A, De Luca A, Rotili D, Valente S, Mai A, Usiello A, Gronemeyer H, Altucci L. Selective class II HDAC inhibitors impair myogenesis by modulating the stability and activity of HDAC-MEF2 complexes. EMBO Rep. 2009 Jul;10(7):776-82. doi: 10.1038/embor.2009.88. Epub 2009 Jun 5.