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Documenti fondamentali

T2580

Sigma-Aldrich

Trapoxin A

≥98% (HPLC), from Helicoma ambiens

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C34H42N4O6
Numero CAS:
Peso molecolare:
602.72
Codice UNSPSC:
12352200
NACRES:
NA.77

Origine biologica

Helicoma ambiens

Livello qualitativo

Saggio

≥98% (HPLC)

Forma fisica

solid

Solubilità

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

Condizioni di spedizione

dry ice

Temperatura di conservazione

−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
GXVXXETYXSPSOA-UFEOFEBPSA-N

Applicazioni

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

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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Nota sulla preparazione

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.

Pittogrammi

Skull and crossbones

Avvertenze

Danger

Indicazioni di pericolo

Consigli di prudenza

Classi di pericolo

Acute Tox. 3 Oral

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


Certificati d'analisi (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)

Articoli

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

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