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Merck
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安全信息

T2580

Sigma-Aldrich

Trapoxin A

≥98% (HPLC), from Helicoma ambiens

别名:

Cyclo((S)-phenylalanyl-(S)-phenylalanyl-(R)-pipecolinyl-(2S,9S)-2-amino-8-oxo-9,10-epoxydecanoyl), RF 1023A

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About This Item

经验公式（希尔记法）:
C34H42N4O6
CAS号:
133155-89-2
分子量:
602.72
UNSPSC代码:
12352200
NACRES:
NA.77

生物来源

Helicoma ambiens

质量水平

200

方案

≥98% (HPLC)

表单

solid

溶解性

DMSO: soluble 0.9-1.10 mg/ml, clear, colorless to faintly yellow (may be further diluted 20 fold in H2O)
chloroform: soluble
methanol: soluble

运输

dry ice

储存温度

−20°C

SMILES字符串

N21[C@H](CCCC2)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C1=O)Cc5ccccc5)Cc4ccccc4)CCCCCC(=O)[C@H]3OC3

InChI

1S/C34H42N4O6/c39-29(30-22-44-30)18-9-3-8-16-25-31(40)36-26(20-23-12-4-1-5-13-23)32(41)37-27(21-24-14-6-2-7-15-24)34(43)38-19-11-10-17-28(38)33(42)35-25/h1-2,4-7,12-15,25-28,30H,3,8-11,16-22H2,(H,35,42)(H,36,40)(H,37,41)/t25-,26-,27-,28+,30-/m0/s1

InChI key

GXVXXETYXSPSOA-UFEOFEBPSA-N

应用

Trapoxin A has been used:
  • to study its effects on the inhibition of histone deacetylase 11 (HDAC11)
  • to study its effects on the inhibition of HDAC3 in human cell lines
  • to study its effects on the inhibition of HDAC6 in rat pyramidal neurons

生化/生理作用

Trapoxin A is a cyclotetrapeptide and a histone deacetylase (HDAC) inhibitor. It increases the level of chromatin acetylation associated with histone H3 at low nanomolar concentrations. Unlike the reversible HDAC inhibition induced by TCA, Trapoxin A irreversibly inhibites HDAC activity in crude cell lysates, and induces the accumulation of hyperacetylated core histones in a number of mammalian cell lines and tissues. Histone acetylation and methylation have been studied extensively for their anti-tumor activities in carcinogenesis and Trapoxin has been suggested as a potential anticancer agent for pre-clinical trials.
Trapoxin is a cyclotetrapeptide and a histone deacetylase (HDAC) inhibitor.

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.

制备说明

Trapoxin A is soluble in DMSO at a concentration ranging from 0.9-1.10 mg/ml and yields a clear, colorless to faint yellow solution. It is also soluble in chloroform and methanol.

象形图

Skull and crossbones
GHS06

警示用语：

Danger

危险声明

H301

预防措施声明

P301 + P310

危险分类

Acute Tox. 3 Oral

储存分类代码

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

新产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000202809
0000202810
0000194379
0000194379
0000202809

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Janine B Lee et al.
The Journal of physiology, 590(7), 1535-1546 (2012-02-15)
The prefrontal cortex (PFC), a region responsible for high-order cognitive functions, such as decision-making, attention and working memory, is highly influenced by stress and corticosteroid stress hormones. Recently it has been shown that acute stress affects PFC functions by potentiating
Shaowen Wang et al.
Novartis Foundation symposium, 259, 238-245 (2004-06-03)
Dynamic changes in the post-translational modification pattern of histories such as acetylation, deacetylation, phosphorylation, methylation and ubiquitination are thought to provide a code for correct regulation of gene expression by affecting chromatin structure and interaction with regulatory factors. Our studies
P Stein et al.
Molecular reproduction and development, 47(4), 421-429 (1997-08-01)
In the preimplantation mouse embryo, activation of the embryonic genome is accompanied by a transient enrichment of histone H4 acetylated at lysines 5, 8, and 12 at the nuclear periphery (Worrad et al., 1995: Development 121:2949-2959). In the present report
Carlos Moreno-Yruela et al.
Cell chemical biology, 25(7), 849-856 (2018-05-08)
Histone deacetylase (HDAC) enzymes regulate diverse biological function, including gene expression, rendering them potential targets for intervention in a number of diseases, with a handful of compounds approved for treatment of certain hematologic cancers. Among the human zinc-dependent HDACs, the
Hua Cao et al.
Blood, 103(2), 701-709 (2003-08-16)
We investigated the induction of human gamma globin gene activity by 3 classes of histone deacetylase inhibitors: amide analogues of trichostatin A, hydroxamic acid analogues of trapoxin, and scriptaid and its analogues. The screening consisted of measuring the effects of
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