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C9492 Sigma-Aldrich

Chaetocin from Chaetomium minutum

≥95% (HPLC)

  • CAS Number 28097-03-2

  • Empirical Formula (Hill Notation) C30H28N6O6S4

  • Molecular Weight 696.84

  •  MDL number MFCD00133163

  •  PubChem Substance ID 24893002

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Properties

Related Categories Bioactive Small Molecules for Epigenetic Research, Epigenetics, Histone Lysine Methyltransferase (HKMT) Inhibitors, Histone Methylation Modulators, Molecular Biology More...
InChI Key   PZPPOCZWRGNKIR-UHFFFAOYSA-N
assay   ≥95% (HPLC)
storage temp.   2-8°C

Description

General description

Chaetocin is a fungal metabolite with antimicrobial and cytostatic activity.1, 2 It belongs to the 3,6-epidithio-diketopiperazines class of which gliotoxin, sporidesmin, aranotin, oryzachloride, verticillin A and the melinacidins are members.1,3 Chaetocin is a molecular dimer of two five-membered rings cis fused. 1 Interestingly, the chirality of the 3,6-epidithio-diketopiperazine moiety in chaetocin is opposite to the chirality in gliotoxin, sporidesmin, aranotin and oryzachloride and while the later compounds show antiviral activity, chaetocin does not.1 This fungal toxin showed strong cytotoxicity against HeLa cells (IC50=0.05 μg/ml).2

Chaetocin was found to be a specific inhibitor of the lysine-specific histone methyltransferase SU(VAR)3-9 (IC50= 0.6 μM) of Drosophila melanogaster and of its human ortholog (IC50= 0.8 μM), and acts as a competitive inhibitor for S-adenosylmethionine.4 The specificity of chaetocin for SU(VAR)3-9 makes this compound an excellent tool for the study of heterochromatin-mediated gene repression.4

References:
1. Weber, H. P., et al., The molecular structure and absolute configuration of chaetocin. Acta Cryst., B28, 2945-2951 (1972).
2. Udagawa, S., et al., The production of chaetoglobosins, sterigmatocystin, O-methylsterigmatocystin, and chaetocin by Chaetomium spp. and related fungi. Can. J. microbiol., 25, 170-177 (1979).
3. Gardiner, D. M., et al., The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis. Microbiol., 151, 1021-1032 (2005).
4. Greiner, D., et al., Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9. Nat. Chem. Biol., 1, 143-145 (2005).

Biochem/physiol Actions

Antibacterial mycotoxin. Specific inhibitor of lysine-specific histone methyltransferase making the compound useful in the study of heterochromatin mediated gene repression. Selective competitive inhibitor of thioredoxin reductase-1 (TrxR1), a putative mechanism of its anticancer activity.

methyltransferase making the compound useful in the study of heterochromatin mediated gene repression. Selective competitive inhibitor of thioredoxin reductase-1 (TrxR1), a putative mechanism of its anticancer activity.

Preparation Note

Soluble in DMSO. At 1 mg/ml the solution is stable for 1 week at 2-8 °C.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
FM3032000

Documents

Certificate of Analysis

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Protocols & Articles

Articles

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, Gene expression, Immunoprecipitation, Indicators, Methylations, Microarray Analysis, PAGE, Polymerase chain reaction, Polymerase chain reaction - quantitative, Polymorphisms, Purification, Sequencing, Transcription, Whole genome amplification

Peer-Reviewed Papers
15

References

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