Molecular structure of Apicidin, CAS Number: 183506-66-3
Apicidin (CAS 183506-66-3)
See product citations (9)
Alternate Names:
Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinexcarbonyl]
Application:
Apicidin is 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.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
QUICK LINKS
Ordering Information
Product Citations
Description
Technical Information
Safety Information
SDS & Certificate of Analysis
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 may act 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-1alpha levels and therefore reduce transcriptional activity of HIF-1 in murine cell lines. Apicidin is an inhibitor of HDAC3 and N-CoR.
Apicidin (CAS 183506-66-3) References
- Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin. | Han, JW., et al. 2000. Cancer Res. 60: 6068-74. PMID: 11085529
- Broad spectrum antiprotozoal agents that inhibit histone deacetylase: structure-activity relationships of apicidin. Part 1. | Colletti, SL., et al. 2001. Bioorg Med Chem Lett. 11: 107-11. PMID: 11206438
- 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. | Singh, SB., et al. 2002. J Org Chem. 67: 815-25. PMID: 11856024
- Apicidin, a histone deacetylase inhibitor, induces differentiation of HL-60 cells. | Hong, J., et al. 2003. Cancer Lett. 189: 197-206. PMID: 12490313
- Regulation of the HIF-1alpha stability by histone deacetylases. | Kim, SH., et al. 2007. Oncol Rep. 17: 647-51. PMID: 17273746
- Apicidin, a histone deaceylase inhibitor, induces both apoptosis and autophagy in human oral squamous carcinoma cells. | Ahn, MY., et al. 2011. Oral Oncol. 47: 1032-8. PMID: 21856210
- Apicidin sensitizes pancreatic cancer cells to gemcitabine by epigenetically regulating MUC4 expression. | Ansari, D., et al. 2014. Anticancer Res. 34: 5269-76. PMID: 25275019
- Apicidin inhibits cell growth by downregulating IGF-1R in salivary mucoepidermoid carcinoma cells. | Ahn, MY., et al. 2015. Oncol Rep. 33: 1899-907. PMID: 25647264
- Histone deacetylase inhibitor apicidin increases expression of the α-secretase ADAM10 through transcription factor USF1-mediated mechanisms. | Hu, XT., et al. 2017. FASEB J. 31: 1482-1493. PMID: 28003340
- Apicidin Inhibited Proliferation and Invasion and Induced Apoptosis via Mitochondrial Pathway in Non-small Cell Lung Cancer GLC-82 Cells. | Zhang, J., et al. 2017. Anticancer Agents Med Chem. 17: 1374-1382. PMID: 28425856
- Apicidin Attenuates MRSA Virulence through Quorum-Sensing Inhibition and Enhanced Host Defense. | Parlet, CP., et al. 2019. Cell Rep. 27: 187-198.e6. PMID: 30943400
- Calmodulin/CaMKII-γ mediates prosurvival capability in apicidin-persistent hepatocellular carcinoma cells via ERK1/2/CREB/c-fos signaling pathway. | Hsu, WC., et al. 2021. J Cell Biochem. 122: 612-625. PMID: 33459431
- Apicidin biosynthesis is linked to accessory chromosomes in Fusarium poae isolates. | Witte, TE., et al. 2021. BMC Genomics. 22: 591. PMID: 34348672
- Retraction Note: Apicidin induces endoplasmic reticulum stress- and mitochondrial dysfunction-associated apoptosis via phospholipase Cγ1- and Ca2+-dependent pathway in mouse Neuro-2a neuroblastoma cells. | Choi, JH., et al. 2022. Apoptosis. 27: 1060. PMID: 36169758
- Apicidin attenuates memory deficits by reducing the Aβ load in APP/PS1 mice. | Luo, B., et al. 2023. CNS Neurosci Ther. 29: 1300-1311. PMID: 36708130
- Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase. | Darkin-Rattray, SJ., et al. 1996. Proc Natl Acad Sci U S A. 93: 13143-7. PMID: 8917558
Inhibitor of:
A830080D01Rik, BUD31, CD42d, GATA-4, GOLGA6L6, H2-M10.3, HDA2, HDA6, HDAC, HDAC2, HDAC3, HDAC5, HERPUD2, HHV-4 EBNA-2, Histone cluster 1 H3G, Histone cluster 1 H3J, Histone cluster 1 H4I, Histone cluster 2 H3B, Histone cluster 3 H2BB, Histone H1, Histone H10, hyccin, IFIT5, IFITM1, IFN-αB, ING5, JRK, KRTAP8-2, LOC100041004, N-CoR, p150, parvalbumin β, PCDHGA8, PCDHGB5, Pericentrin 2, RFX8, SMRT/SMRTe, TCEAL8, TTC1, ZFP106, ZKSCAN2, ZNF161, and ZNF276.Activator of:
C1orf94, Clm3, granzyme D, Histone cluster 1 H2AH, Histone cluster 1 H2BC, Histone cluster 1 H2BI, Histone cluster 1 H3C, Histone cluster 1 H3E, Histone cluster 1 H3J, Histone cluster 1 H4F, Histone cluster 2 H3C, Histone cluster 2 H3D, Histone cluster 2 H4, INO80B, LOC100041231, RBBP1, ZNF226, and ZNF597.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Apicidin, 1 mg | sc-202061 | 1 mg | $110.00 | |||
Apicidin, 5 mg | sc-202061A | 5 mg | $343.00 |