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A8851

Sigma-Aldrich

Apicidin

≥98% (HPLC), from microbial

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C34H49N5O6
Numéro CAS:
183506-66-3
Poids moléculaire :
623.78
Numéro MDL:
MFCD03452661
Code UNSPSC :
12352200
ID de substance PubChem :
329771019
Nomenclature NACRES :
NA.77

Source biologique

microbial

Niveau de qualité

200

Stérilité

non-sterile

Pureté

≥98% (HPLC)

Forme

solid

Solubilité

DMSO: ~1 mg/mL

Spectre d'activité de l'antibiotique

parasites

Mode d’action

enzyme | inhibits

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

[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

Clé InChI

JWOGUUIOCYMBPV-PYAAAQPJSA-N

Catégories apparentées

Description générale

Apicidin is a cyclic tetrapeptide fungal metabolite.

Application

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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Articles

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

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