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Sigma-Aldrich

Histone Deacetylase Inhibitor IV

The Histone Deacetylase Inhibitor IV, also referenced under CAS 537034-15-4, controls the biological activity of Histone Deacetylase. This small molecule/inhibitor is primarily used for Cell Structure applications.

Synonym(s):

Histone Deacetylase Inhibitor IV, N¹-(2-Aminophenyl)-N⁷-phenylheptanediamide

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About This Item

Empirical Formula (Hill Notation):
C19H23N3O2
CAS Number:
537034-15-4
Molecular Weight:
325.40
UNSPSC Code:
12352200

Quality Level

100

Assay

≥97% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

beige

solubility

DMSO: 100 mg/mL
methanol: 5 mg/mL

shipped in

ambient

storage temp.

−20°C

InChI

1S/C19H23N3O2/c20-16-11-7-8-12-17(16)22-19(24)14-6-2-5-13-18(23)21-15-9-3-1-4-10-15/h1,3-4,7-12H,2,5-6,13-14,20H2,(H,21,23)(H,22,24)

InChI key

ZAIULUYKQLVQFH-UHFFFAOYSA-N

General description

A cell-permeable pimeloylanilide compound that acts as a FXN- (frataxin gene) specific HDAC (histone deacetylase) inhibitor. Reverses the silencing of FXN transcription in FRDA (Friedreich′s ataxia) cells (~3-fold increase of FXN mRNA at 5 µM in primary FRDA lymphocytes and ~3-fold frataxin expression in FRDA cell line at 2.5 µM) due to hypoacetylation of histones H3 and H4 by increasing acetylation at H3K14, H4K5 and H4K12, without significant changes in acetylation at H3K9, H4K8 and H4K16. In comparison, Trichostatin-A (Cat. No. 647925 and 647926) and SAHA, two other commonly used HDAC inhibitors, exhibit no effect on FXN transcription.
A cell-permeable pimeloylanilide compound that acts as a FXN- (frataxin gene) specific HDAC (histone deacetylase) inhibitor. Reverses the silencing of FXN transcription in FRDA (Friedreich′s ataxia) cells (~3-fold increase of FXN mRNA at 5 µM in primary FRDA lymphocytes and ~3-fold frataxin expression in FRDA cell line at 2.5 µM) due to hypoacetylation of histones H3 and H4 by increasing acetylation at H3K14, H4K5 and H4K12, without significant changes in acetylation at H3K9, H4K8 and H4K16. In comparison, Trichostatin-A (Cat. No. 647925 and 647926) and SAHA, two other commonly used HDAC inhibitors, exhibit no effect on FXN transcription.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Histone Deacetylase
Product does not compete with ATP.
Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Harmful (C)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Herman, D., et al. 2006. Nat. Chem. Biol.2, 551.

Legal Information

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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