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T2580

Sigma-Aldrich

Trapoxin A

≥98% (HPLC), from Helicoma ambiens

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Synonym(s):
Cyclo((S)-phenylalanyl-(S)-phenylalanyl-(R)-pipecolinyl-(2S,9S)-2-amino-8-oxo-9,10-epoxydecanoyl), RF 1023A
Empirical Formula (Hill Notation):
C34H42N4O6
CAS Number:
133155-89-2
Molecular Weight:
602.72
UNSPSC Code:
12352200
NACRES:
NA.77

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

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

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.

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

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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
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
[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)
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