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A8851

Sigma-Aldrich

Apicidin

≥98% (HPLC), from microbial

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C34H49N5O6
CAS-Nummer:
183506-66-3
Molekulargewicht:
623.78
MDL-Nummer:
MFCD03452661
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329771019
NACRES:
NA.77

Biologische Quelle

microbial

Qualitätsniveau

200

Sterilität

non-sterile

Assay

≥98% (HPLC)

Form

solid

Löslichkeit

DMSO: ~1 mg/mL

Wirkungsspektrum von Antibiotika

parasites

Wirkungsweise

enzyme | inhibits

Versandbedingung

wet ice

Lagertemp.

−20°C

SMILES String

[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

InChIKey

JWOGUUIOCYMBPV-PYAAAQPJSA-N

Allgemeine Beschreibung

Apicidin is a cyclic tetrapeptide fungal metabolite.

Anwendung

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.

Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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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