LKT Labs

Biochemicals for Life Science Research

Apicidin

Product ID A6132
Cas No. 183506-66-3
Purity ≥98%
Product Unit SizeCostQuantityStock
1 mg $102.10 In stock
5 mg $381.50 In stock
10 mg $678.60 Please Inquire
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Description

Apicidin is a cyclic tetrapeptide that inhibits histone deacetylase (HDAC) and exhibits anticancer benefit. In oral squamous cell carcinoma cells, apicidin upregulates expression of p21, inducing G2/M phase cell cycle arrest, apoptosis, and autophagy. In non-small cell lung cancer (NSCLC) cells, apicidin downregulates expression of checkpoint kinase (CHK) 1, decreases phosphorylation of cdc25C and cdc2, and upregulates expression of cdc25A, inducing apoptotic cell death. Additionally, apicidin increases apoptosis in Brc-Abl positive leukemia cells through disruption of the mitochondrial membrane potential, activation of caspases 3, 8, and 9, cleavage of poly(ADP)-ribose polymerase (PARP), and release of cytochrome c. Apicidin also induces apoptosis in eosinophils and neutrophils.

Product Info

Cas No.

183506-66-3
Purity

≥98%
Formula

C34H49N5O6
Formula Wt.

623.78
IUPAC Name

methyl 6-[(3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxyindol-3-yl)methyl]-2,5,8, 11-tetraoxo-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-9-yl]hexanoate InChI: InChI=1S/C33H47N5O7/c1-5-21(2)29-33(43)37-18-12-11-16-27(37)32(42)34-24 (14-7-6-8-17-28(39)44-3)30(40)35-25(31(41)36-29)19-22-20-38(45-4)26-15- 10-9-13-23(22)26/h9-10,13,15,20-21,24-25,27,29H,5-8,11-12,14,16-19H2, 1-4H3,(H,34,42)(H,35,40)(H,36,41)/t21?,24-,25-,27+,29-/m0/s1
Melting Point

190°C
Solubility

Ethano (0.9 mg/mL)l, DMSO (0.9 mg/mL), Dichloromethane. Slightly soluble in water, methanol
Appearance

White Crystal Powder

Shipping and Storage

Store Temp

4°C
Ship Temp

Ambient

Downloads

MSDS

A6132 MSDS PDF
Info Sheet

A6132 Info Sheet PDF
Brochures

Epigenetic Modifiers Booklet

References

Ahn MY, Ahn SG, Yoon JH. Apicidin, a histone deaceylase inhibitor, induces both apoptosis and autophagy in human oral squamous carcinoma cells. Oral Oncol. 2011 Nov;47(11):1032-8. PMID: 21856210.

Brazelle W, Kreahling JM, Gemmer J, et al. Histone deacetylase inhibitors downregulate checkpoint kinase 1 expression to induce cell death in non-small cell lung cancer cells. PLoS One. 2010 Dec 14;5(12):e14335. PMID: 21179472.

Kankaanranta H, Janka-Junttila M, Ilmarinen-Salo P, et al. Histone deacetylase inhibitors induce apoptosis in human eosinophils and neutrophils. J Inflamm (Lond). 2010 Feb 4;7:9. PMID: 20181093.

Cheong JW, Chong SY, Kim JY, et al. Induction of apoptosis by apicidin, a histone deacetylase inhibitor, via the activation of mitochondria-dependent caspase cascades in human Bcr-Abl-positive leukemia cells. Clin Cancer Res. 2003 Oct 15;9(13):5018-27. PMID: 14581377.

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