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A8851

Sigma-Aldrich

Apicidin

≥98% (HPLC), from microbial

Sinonimo/i:

Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinexcarbonyl]

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About This Item

Formula empirica (notazione di Hill):
C34H49N5O6
Numero CAS:
183506-66-3
Peso molecolare:
623.78
Numero MDL:
MFCD03452661
Codice UNSPSC:
12352200
ID PubChem:
329771019
NACRES:
NA.77

Origine biologica

microbial

Livello qualitativo

200

Sterilità

non-sterile

Saggio

≥98% (HPLC)

Forma fisica

solid

Solubilità

DMSO: ~1 mg/mL

Spettro attività antibiotica

parasites

Modalità d’azione

enzyme | inhibits

Condizioni di spedizione

wet ice

Temperatura di conservazione

−20°C

Stringa SMILE

[H][C@]12CCCCN1C(=O)[C@@H](NC(=O)[C@H](Cc3cn(OC)c4ccccc34)NC(=O)[C@H](CCCCCC(=O)CC)NC2=O)C(C)CC

InChI

1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22?,26-,27-,29+,30?/m0/s1
JWOGUUIOCYMBPV-PYAAAQPJSA-N

Categorie correlate

Descrizione generale

Apicidin is a cyclic tetrapeptide fungal metabolite.

Applicazioni

Apicidin has been used as a histone deacetylase 2 (HDAC2) inhibitor to study its effects on 5-lipoxygenase (5-LO) mRNA expression in cell lines of Mono Mac6. It has also been used to study the effects of toll-like receptor 8 (TLR-8) stimulation and histone modification on the expression of an activator protein 1 [AP-1] family member(Fra-2) and tissue inhibitor of metalloproteinases 1 (TIMP-1) in monocytes.

Azioni biochim/fisiol

Apicidin is a potent inhibitor of histone deacetylase (HDAC). It particularlyinhibits histone deacetylase 1 and 3 (HDAC1 and HDAC3). Apicidin exhibits anti-protozoal activity against apicomplexan metabolite produced by parasites. It also possesses anti-proliferative activity against several cancer cell lines. Apicidin shows anti-cancer activity against human acute promyelocytic leukemia cell.

Caratteristiche e vantaggi

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Kwon, S.H., et al.
The Journal of Biological Chemistry, 18, 2073-2073 (2002)
J S Kim et al.
Biochemical and biophysical research communications, 281(4), 866-871 (2001-03-10)
Apicidin [cyclo(N-O-methyl-L-tryptophanyl-L-isoleucinyl-D-pipecolinyl-l-2-amino-8-oxodecanoyl)], a novel histone deacetylase inhibitor, has been identified as an antiprotozoal and antiproliferative agent. In this study, we show apicidin induces transcriptional activation of p21(WAF1/CIP1) (p21) in human prostate carcinoma cells. Apicidin induces expression of p21 protein and
Beatrix Meltzer et al.
Virology, 518, 241-252 (2018-03-20)
In HIV infected macrophages, a large population of viral genomes persists as the unintegrated form (uDNA) that is transcriptionally active. However, how this transcriptional activity is controlled remains unclear. In this report, we investigated whether Tat, the viral transactivator of
J W Han et al.
Cancer research, 60(21), 6068-6074 (2000-11-21)
Apicidin [cyclo(N-O-methyl-L-tryptophanyl-L-isoleucinyl-D-pipecolinyl -L-2-amino-8-oxodecanoyl)] is a fungal metabolite shown to exhibit antiparasitic activity by the inhibition of histone deacetylase (HDAC). In this study, we evaluated apicidin as a potential antiproliferative agent. Apicidin showed a broad spectrum of antiproliferative activity against various
Jeong Gu Kang et al.
Scientific reports, 9(1), 11960-11960 (2019-08-21)
Despite the increased interest in epigenetic research, its progress has been hampered by a lack of satisfactory tools to control epigenetic factors in specific genomic regions. Until now, many attempts to manipulate DNA methylation have been made using drugs but
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