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Key Documents

T2580

Sigma-Aldrich

Trapoxin A

≥98% (HPLC), from Helicoma ambiens

同義詞:

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

經驗公式(希爾表示法):
C34H42N4O6
CAS號碼:
分子量::
602.72
分類程式碼代碼:
12352200
NACRES:
NA.77

生物源

Helicoma ambiens

品質等級

化驗

≥98% (HPLC)

形狀

solid

溶解度

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

運輸包裝

dry ice

儲存溫度

−20°C

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 密鑰

GXVXXETYXSPSOA-UFEOFEBPSA-N

應用

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.

特點和優勢

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.

準備報告

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.

象形圖

Skull and crossbones

訊號詞

Danger

危險聲明

防範說明

危險分類

Acute Tox. 3 Oral

儲存類別代碼

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

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


分析證明 (COA)

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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
Chemistry as a vector for understanding biology.
Christen Brownlee
ACS chemical biology, 2(9), 595-598 (2007-09-27)
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
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
[A mammalian histone deacetylase related to the yeast transcriptional regulator Rpd3p].
Hidenori Nakajima
Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme, 52(13 Suppl), 1790-1791 (2007-12-07)

文章

Epigenetic modifications are thought to occur through two key interconnected processes—DNA methylation and the covalent modification of histones.

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