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A8851

Apicidin

Name: Apicidin
Brand: SIGMA

≥98% (HPLC), from microbial

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₃₄H₄₉N₅O₆

CAS Number:

183506-66-3

Molecular Weight:

623.78

NACRES:

NA.77

PubChem Substance ID:

329771019

UNSPSC Code:

12352200

MDL number:

MFCD03452661

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

200

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Properties

biological source

microbial

Quality Level

200

sterility

non-sterile

assay

≥98% (HPLC)

form

solid

solubility

DMSO: ~1 mg/mL

antibiotic activity spectrum

parasites

mode of action

enzyme | inhibits

shipped in

wet ice

storage temp.

−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

InChI key

JWOGUUIOCYMBPV-PYAAAQPJSA-N

Description

General description

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.

Biochem/physiol Actions

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.

Potent (nM) cell permeable inhibitor of histone deacetylase.

Features and Benefits

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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