A hydroxamate-based HDAC inhibitor
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LAQ824

Item No. 16427

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E)-N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2-propenamide
CAS Number
404951-53-7
Synonyms
  • Dacinostat
  • NVP-LAQ824
Molecular Formula
C22H25N3O3
Formula Weight
379.5
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 50 mg/ml
λmax
222, 281, 352 nm
SMILES
O=C(NO)/C=C/C1=CC=C(CN(CCC2=CNC3=C2C=CC=C3)CCO)C=C1
InChi Code
InChI=1S/C22H25N3O3/c26-14-13-25(12-11-19-15-23-21-4-2-1-3-20(19)21)16-18-7-5-17(6-8-18)9-10-22(27)24-28/h1-10,15,23,26,28H,11-14,16H2,(H,24,27)/b10-9+
InChi Key
BWDQBBCUWLSASG-MDZDMXLPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    LAQ824 is a hydroxamate-based inhibitor of histone deacetylases (HDACs) with an IC50 value of 30 nM.1,2 It inhibits the growth of colon, breast, prostate, and non-small cell lung cancer cell lines at concentrations of less than 1 µM.1,3 LAQ824 augments the actions of fludarabine (Item No. 14128) and imatinib mesylate (Item No. 13139) in human leukemia cells.4,5 Through its effects on HDACs, LAQ824 induces acetylation of histones, α-tubulin, and heat shock protein 90 (Hsp90).5,6 Acetylation of Hsp90 blocks its chaperone function, resulting in changes in levels of several client proteins, including estrogen receptor-α, Hsp72, and Raf-1.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Catley, L., Weisberg, E., Tai, Y.T., et al. NVP-LAQ824 is a potent novel histone deacetylase inhibitor with significant activity against multiple myeloma. Blood 102(7), 2615-2622 (2003).

    2. Dokmanovic, M., Clarke, C., and Marks, P.A. Histone deacetylase inhibitors: Overview and perspectives. Mol. Cancer Res. 5(10), 981-989 (2007).

    3. Zheng, Y.G., Wu, J., Chen, Z., et al. Chemical regulation of epigenetic modifications: Opportunities for new cancer therapy. Med. Res. Rev. 28(5), 645-687 (2008).

    4. Rosato, R.R., Almenara, J.A., Maggio, S.C., et al. Role of histone deacetylase inhibitor-induced reactive oxygen species and DNA damage in LAQ-824/fludarabine antileukemic interactions. Mol. Cancer Ther. 7(10), 3285-3297 (2008).

    5. Nimmanapalli, R., Fuino, L., Bali, P., et al. Histone deacetylase inhibitor LAQ824 both lowers expression and promotes proteasomal degradation of Bcr-Abl and induces apoptosis of imatinib mesylate-sensitive or -refractory chronic myelogenous leukemia-blast crisis cells. Cancer Res. 63(16), 5126-5135 (2003).

    6. Fiskus, W., Ren, Y., Mohapatra, A., et al. Hydroxamic acid analogue histone deacetylase inhibitors attenuate estrogen receptor-α levels and transcriptional activity: A result of hyperacetylation and inhibition of chaperone function of heat shock protein 90. Clin. Cancer Res. 13(16), 4882-4890 (2007).

    7. de Bono, J.S., Kristeleit, R., Tolcher, A., et al. Phase I pharmacokinetic and pharmacodynamic study of LAQ824, a hydroxamate histone deacetylase inhibitor with a heat shock protein-90 inhibitory profile, in patients with advanced solid tumors. Clin. Cancer Res. 14(20), 6663-6673 (2008).