Apicidin An HDAC inhibitor and apoptosis inducer

Apicidin (CAS 183506-66-3)

Apicidin | CAS 183506-66-3 is rated 4.0 out of 5 by 1.
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Synonym: Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinexcarbonyl]
Application: An HDAC inhibitor and apoptosis inducer
CAS Number: 183506-66-3
Purity: ≥95%
Molecular Weight: 623.78
Molecular Formula: C34H49N5O6
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Apicidin, a fungal metabolite, contains potent and broad antiprotozoal characteristics in vitro against Apicomplexan parasites. This compound has also been shown to be active in mice against Plasmodium berghei. Apicidin is an HDAC inhibitor. Mechanistic studies utilizing Apicidin inhibition in low nanomolar concentration has been shown to cause hyperacetylation of histones in the Apicomplexan HDAC (histone deacetylase), which causes hyperacetylation of histones within the parasite. It has been reported that Apicidin also contains a wide range of antiproliferative activity against various cancer cell lines in mice, again through HDAC inhibition. Apicidin has also been shown to stimulate apoptosis via induction of Fas/Fas ligand. Furthermore, it has been reported to dramatically decrease HIF-1α levels and therefore reduce transcriptional activity of HIF-1 in murine cell lines. Apicidin is an inhibitor of HDAC3 and N-CoR.


References

1. Darkin-Rattray, S J., et al., 1996. Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase. Proceedings of the National Academy of Sciences of the United States of America. 93(23): 13143-7. PMID: 8917558
2. Han, J W., et al., 2000. Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin. Cancer research. 60(21): 6068-74. PMID: 11085529
3. Colletti, S L., et al., 2001. Broad spectrum antiprotozoal agents that inhibit histone deacetylase: structure-activity relationships of apicidin. Part 1. Bioorganic & medicinal chemistry letters. 11(2): 107-11. PMID: 11206438
4. Singh, Sheo B., et al., 2002. Structure and chemistry of apicidins, a class of novel cyclic tetrapeptides without a terminal alpha-keto epoxide as inhibitors of histone deacetylase with potent antiprotozoal activities. The Journal of organic chemistry. 67(3): 815-25. PMID: 11856024
5. Hong, JangJa., et al., 2003. Apicidin, a histone deacetylase inhibitor, induces differentiation of HL-60 cells. Cancer letters. 189(2): 197-206. PMID: 12490313
6. Kim, Se-Hee., et al., 2007. Regulation of the HIF-1alpha stability by histone deacetylases. Oncology reports. 17(3): 647-51. PMID: 17273746

Physical State :
Solid
Derived From :
Fusarium sp.
Solubility :
Soluble in DMSO (~1 mg/mL), acetonitrile (~1 mg/mL), ethanol (1 mg/mL), and methanol.
Storage :
Store at -20° C
Melting Point :
190° C
Refractive Index :
n20D 1.62
IC50 :
HDACs: IC50 = 0.7 nM (Apicomplexan parasites); HDAC3: IC50 = 8 nM; p21: IC50 = 0.5-2 µM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
467801
MDL Number :
MFCD03452661
SMILES :
CCC(C)[C@H]1C(=O)N2CCCC[C@@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC3=CN(C4=CC=CC=C43)OC)CCCCCC(=O)CC

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Apicidin  Product Citations

See how others have used Apicidin. Click on the entry to view the PubMed entry .

Citations 1 to 7 of 7 total

PMID: # 27869761  Springler, A. et al. 2016. Toxins (Basel). 8:

PMID: # 26912657  Ha, SD. et al. 2016. J. Biol. Chem. 291: 8745-55.

PMID: # 25316709  Nicholas, D. et al. 2015. Mol. Cell Proteomics. 14: 15-29.

PMID: # 18275843  Kim, YK. et al. 2008. Biochem. Biophys. Res. Commun. 368: 959-964.

PMID: # 16870149  Kim, YK. et al. 2006. Biochem. Biophys. Res. Commun. 347: 1088-1093.

PMID: # 12490313  Hong, J. et al. 2003. Cancer Lett. 189: 197-206.

PMID: # 11551946  Han, JW. et al. 2001. J. Biol. Chem. 276: 42084-42090.

Citations 1 to 7 of 7 total

How long will this product be stable at 4°C?

Asked by: Io5ay
Thank you for your question. We do not know the half life of this chemical, Apicidin: sc-202061, but based on our experience Apicidin (solid) should be stable at 4°C for more than a few weeks.
Answered by: Technical Support
Date published: 2016-12-15
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Rated 4 out of 5 by from Product sc Product sc-202061 was successfully used to study Histone H2B acetylation. An increase in acetylated H2B is observed by WB in HeLa cells. -SCBT QC
Date published: 2015-03-10
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