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T2580

Trapoxin A

Name: Trapoxin A
Brand: SIGMA

From Helicoma ambiens, ≥98% (HPLC), cyclotetrapeptide and a histone deacetylase (HDAC) inhibitor, solid

别名:

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

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关于此项目

经验公式（希尔记法）:

C₃₄H₄₂N₄O₆

化学文摘社编号:

133155-89-2

分子量:

602.72

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

200

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属性

产品名称

Trapoxin A, ≥98% (HPLC), from Helicoma ambiens

biological source

Helicoma ambiens

Quality Level

200

assay

≥98% (HPLC)

form

solid

solubility

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

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

说明

Application

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

Biochem/physiol Actions

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.

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.

Preparation Note

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.

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

存储类别

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

107M4061V

119K4026

119K4026V

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商品

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Chemistry as a vector for understanding biology.

Christen Brownlee

ACS chemical biology, 2(9), 595-598 (2007-09-27)

Inhibition of histone deacetylases: a new strategy to target epigenetic modifications for anticancer treatment.

U H Weidle et al.

Anticancer research, 20(3A), 1471-1485 (2000-08-06)

The role of epigenetic modifications due to deregulated acetylation of nucleosomes with respect to its role in progression and etiology of human cancer is discussed. Among the mediators of these phenomena are the histone deacetylases, a class of enzymes consisting

Induction of human gamma globin gene expression by histone deacetylase inhibitors.

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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全球贸易项目编号

货号	GTIN
T2580-1MG	04061826274712
T2580-5MG	04061832649436