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SML0313

Sigma-Aldrich

Pimelic Diphenylamide 106

≥98% (HPLC)

Synonym(s):

Compound 106, Inhibitor 106, N1-(2-Aminophenyl)-N7-(4-methylphenyl)-heptanediamide, RGFA 8, TC-H 106

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About This Item

Empirical Formula (Hill Notation):
C20H25N3O2
CAS Number:
937039-45-7
Molecular Weight:
339.43
MDL number:
MFCD17010287
UNSPSC Code:
12352200
PubChem Substance ID:
329825318
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: ≥15 mg/mL

storage temp.

2-8°C

SMILES string

Cc1ccc(NC(=O)CCCCCC(=O)Nc2ccccc2N)cc1

InChI

1S/C20H25N3O2/c1-15-11-13-16(14-12-15)22-19(24)9-3-2-4-10-20(25)23-18-8-6-5-7-17(18)21/h5-8,11-14H,2-4,9-10,21H2,1H3,(H,22,24)(H,23,25)

InChI key

WTKBRPXPNAKVEQ-UHFFFAOYSA-N

Biochem/physiol Actions

106 is a Class I HDAC inhibitor, demonstrating no activity against class II HDACs. It is a slow, tight-binding inhibitor of HDACs 1, 2, and 3, with a preference toward HDAC3 with Ki of 14 nM, 15 times lower than the Ki for HDAC1.
Pimelic diphenylamides has the ability to enhance the expression of the frataxin gene in lymphocytes from Friedreich ataxia patients.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Pimelic diphenylamide 106 is a slow, tight-binding inhibitor of class I histone deacetylases
Chou CJ, et al.
The Journal of Biological Chemistry, 283(51), 35402-35409 (2008)
Yifei Liao et al.
PLoS pathogens, 17(2), e1009307-e1009307 (2021-02-18)
Marek's disease virus (MDV) is a potent oncogenic alphaherpesvirus that elicits a rapid onset of malignant T-cell lymphomas in chickens. Three MDV types, including GaHV-2 (MDV-1), GaHV-3 (MDV-2) and MeHV-1 (HVT), have been identified and all encode a US3 protein
Jason A Pfister et al.
PloS one, 14(4), e0215208-e0215208 (2019-04-12)
SIRT1, a NAD+-dependent deacetylase, protects neurons in a variety of in vitro and in vivo models of neurodegenerative disease. We have previously described a neuroprotective effect by SIRT1 independent of its catalytic activity. To confirm this conclusion we tested a
Angela K Carrillo et al.
Bioorganic & medicinal chemistry, 23(16), 5151-5155 (2015-02-01)
Two of the histone deacetylases, TbDAC1 and TbDAC3, have been reported to be essential genes in trypanosomes. Therefore, we tested the activity of a panel of human histone deacetylase inhibitors (HDACi) for their ability to block proliferation of Trypanosoma brucei
Dominik Stammler et al.
Journal of immunology (Baltimore, Md. : 1950), 195(11), 5421-5431 (2015-11-01)
Histone deacetylase (HDAC) inhibitors (HDACi) are clinically approved anticancer drugs that have important immune-modulatory properties. We report the surprising finding that HDACi promote LPS-induced IL-1β processing and secretion in human and murine dendritic cells and murine macrophages. HDACi/LPS-induced IL-1β maturation

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