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T2580

Sigma-Aldrich

Trapoxin A

≥98% (HPLC), from Helicoma ambiens

Sinônimo(s):

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

Fórmula empírica (Notação de Hill):
C34H42N4O6
Número CAS:
Peso molecular:
602.72
Código UNSPSC:
12352200
NACRES:
NA.77

fonte biológica

Helicoma ambiens

Nível de qualidade

Ensaio

≥98% (HPLC)

forma

solid

solubilidade

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

Condições de expedição

dry ice

temperatura de armazenamento

−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

chave InChI

GXVXXETYXSPSOA-UFEOFEBPSA-N

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Nota de preparo

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.

Pictogramas

Skull and crossbones

Palavra indicadora

Danger

Frases de perigo

Declarações de precaução

Classificações de perigo

Acute Tox. 3 Oral

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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John Nielsen
Current opinion in chemical biology, 6(3), 297-305 (2002-05-23)
Combinatorial syntheses allow production of compound libraries in an expeditious and organized manner immediately applicable for high-throughput screening. Natural products possess a pedigree to justify quality and appreciation in drug discovery and development. Currently, we are seeing a rapid increase
P L Sheridan et al.
Genes & development, 11(24), 3327-3340 (1998-02-07)
Specific inhibitors of histone deacetylase, such as trichostatin A (TSA) and trapoxin (TPX), are potent inducers of HIV-1 transcription in latently infected T-cell lines. Activation of the integrated HIV-1 promoter is accompanied by the loss or rearrangement of a positioned
[A new target of cancer therapy: advances in the study of histone deacetylase].
Ai-Lin Liu et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 40(7), 585-590 (2005-10-04)
R Furumai et al.
Proceedings of the National Academy of Sciences of the United States of America, 98(1), 87-92 (2001-01-03)
Trichostatin A (TSA) and trapoxin (TPX) are potent inhibitors of histone deacetylases (HDACs). TSA is proposed to block the catalytic reaction by chelating a zinc ion in the active-site pocket through its hydroxamic acid group. On the other hand, the
Chemistry as a vector for understanding biology.
Christen Brownlee
ACS chemical biology, 2(9), 595-598 (2007-09-27)

Artigos

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