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安全信息

A8851

Sigma-Aldrich

Apicidin

≥98% (HPLC), from microbial

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别名:
Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinexcarbonyl]
经验公式（希尔记法）:
C34H49N5O6
CAS号:
183506-66-3
分子量:
623.78
MDL编号:
MFCD03452661
UNSPSC代码:
12352200
PubChem化学物质编号:
329771019
NACRES:
NA.77

生物来源

microbial

质量水平

200

无菌性

non-sterile

检测方案

≥98% (HPLC)

形式

solid

溶解性

DMSO: ~1 mg/mL

抗生素抗菌谱

parasites

作用机制

enzyme | inhibits

运输

wet ice

储存温度

−20°C

SMILES字符串

[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

相关类别

一般描述

Apicidin is a cyclic tetrapeptide fungal metabolite.

应用

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.

生化/生理作用

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.

特点和优势

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.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

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

法规信息

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Kwon, S.H., et al.
The Journal of Biological Chemistry, 18, 2073-2073 (2002)
Marzena Ciechomska et al.
European journal of clinical investigation, 47(8), 555-564 (2017-06-24)
Systemic sclerosis (SSc) is a chronic autoimmune disease characterised by tissue fibrosis and immune abnormalities. Recent evidence suggests that activated circulating monocytes from patients with SSc play an important role in early stages of SSc pathogenesis due to enhanced expression
Seong Hwan Kim et al.
Biochemical and biophysical research communications, 315(4), 964-970 (2004-02-27)
Apicidin has been identified as a histone deacetylase (HDAC) inhibitor. Since HDAC inhibitors are emerging as an exciting new class of potential anti-cancer agents, in the present study, we have examined the inhibitory effect of apicidin on cancer invasion and
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
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
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