A tight-binding inhibitor of class I HDACs
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Pimelic Diphenylamide 106

Item No. 13212

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N1-(2-aminophenyl)-N7-(4-methylphenyl)-heptanediamide
CAS Number
937039-45-7
Synonyms
  • TC-H 106
  • Histone Deacetylase Inhibitor VII
Molecular Formula
C20H25N3O2
Formula Weight
339.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/mlEthanol: 0.3 mg/ml
λmax
205, 243, 288 nm
SMILES
O=C(CCCCCC(=O)Nc1ccccc1N)Nc1ccc(C)cc1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $29

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    5 mg

    $90

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    10 mg

    $161

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    25 mg

    $354

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    Product Description

    Pimelic diphenylamide 106 is a slow, tight-binding inhibitor of class I histone deacetylases (HDACs).1 Unlike the HDAC inhibitor suberoylanilide hydroamic acid, which has a fast-on/fast-off HDAC binding rate, pimelic diphenylamide 106 progressively binds HDACs and remains bound after wash-out. As a result, the IC50 of pimelic diphenylamide 106 decreases over time. With prolonged preincubation (1-3 hours), pimelic diphenylamide inhibits the class I HDACs (IC50 = 150, 760, 370, and 5,000 nM for HDAC1, 2, 3, and 8, respectively) but not the class II HDACs (IC50 > 180 μM for HDAC4, 5, and 7).1 Pimelic diphenylamide 106 and related benzamide HDAC inhibitors may have therapeutic value in Friedrich’s ataxia1,2,3 and Huntington’s disease,4 in part due to their low animal toxicity.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chou, C.J., Herman, D., and Gottesfeld, J.M. Pimelic diphenylamide 106 is a slow, tight-binding inhibitor of class I histone deacetylases. The Journal of Biological Chemisty 283(51), 35402-35409 (2008).

    2. Rai, M., Soragni, E., Jenssen, K., et al. HDAC inhibitors correct frataxin deficiency in a Friedreich ataxia mouse model. PLoS One 3(4), (2008).

    3. Herman, D., Jenssen, K., Burnett, R., et al. Histone deacetylase inhibitors reverse gene silencing in Friedreich’s ataxia. Nat. Chem. Biol. 2(10), 551-558 (2006).

    4. Thomas, E.A., Coppola, G., Desplats, P.A., et al. The HDAC inhibitor 4b ameliorates the disease phenotype and transcriptional abnormalities in Huntington’s disease transgenic mice. Proc. Natl. Acad. Sci. USA 105(40), 15564-15569 (2008).