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T2580 Sigma-Aldrich

Trapoxin A

≥98% (HPLC), from Helicoma ambiens

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

  • CAS Number 133155-89-2

  • Empirical Formula (Hill Notation) C34H42N4O6

  • Molecular Weight 602.72

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Bioactive Small Molecules for Epigenetic Research, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   200
biological source   Helicoma ambiens
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

Description

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.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Discover Bioactive Small Molecules for Gene Regulation

The loss of regulation of gene expression is a key component to many human disease states, including neurodegenerative disorders, autoimmune conditions and, most prominently, cancers. Regulation of g...
Keywords: Acetylations, Epigenetics, Gene expression, Genomics, Methylations, PAGE, Post translational modifications, Transcription

Histone Modification and Chromatin Remodeling

Gene expression is governed by complex mechanisms including transcription factor binding to DNA and coordinated changes in chromatin structure. The primary protein components of chromatin are the his...
Savita Bagga, PhD.
BioFiles v7 n3, 2012, 10–16
Keywords: Acetylations, Amplification, Cancer, Cell culture, Chromatin immunoprecipitation, Cloning, DNA purification, Diseases, Epigenetics, Gene expression, Immunoprecipitation, Indicators, Methylations, Microarray Analysis, Polymerase chain reaction, Polymerase chain reaction - quantitative, Polymorphisms, Purification, Sequencing, Transcription, Whole genome amplification

Peer-Reviewed Papers
15

References

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