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HomeProduct name listChaetocin

Chaetocin

Synonym(s):(+)-Chaetocin A;EHMT2/G9a Inhibitor II, HMT Inhibitor II, Histone Lysine Methyltransferase Inhibitor II;HMT Inhibitor II, Histone Lysine Methyltransferase Inhibitor II, EHMT2/G9a Inhibitor II;HMTase Inhibitor II, Chaetocin - CAS 28097-03-2 - Calbiochem

  • CAS NO.:28097-03-2
  • Empirical Formula: C30H28N6O6S4
  • Molecular Weight: 696.84
  • MDL number: MFCD00133163
  • EINECS: 200-258-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-06-30 15:45:59
Chaetocin Structural

What is Chaetocin?

Description

Chaetocin (28097-69-1) is an antimicrobial fungal metabolite. It was found to be a specific inhibitor of the lysine-specific histone methyltransferase SU(VAR)3-9 (IC50 = 0.6 mM) of Drosophila melanogaster and of its human ortholog (IC50 = 0.8 mM). It acts as a competitive inhibitor for S-adenosylmethionine. The specificity of chaetocin for SU(VAR)3-9 makes this compound an excellent tool for the study of heterochromatin-mediated gene repression. Chaetocin has an antimyeloma activity which has been linked to induction of oxidative stress and subsequent apoptosis.

Chemical properties

Chaetocin is supplied as a crystalline solid. A stock solution may be made by dissolving the chaetocin in the solvent of choice, which should be purged with an inert gas. Chaetocin is soluble in organic solvents such as DMSO. The solubility of chaetocin in DMSO is approximately 25 mg/ml.

The Uses of Chaetocin

Chaetocin is an epithiodioxopiperazine antibiotic that has recently shown promise as a selective antitumour agent. Chaetocin is an inhibitor of lysine-specific methyltransferase SU(VAR)3-9 both in vitro and in vivo. Chaetocin is dramatically accumulated in cancer cells via a process inhibited by glutathione. Inside the cell, its activity is mediated by the imposition of oxidative stress.

What are the applications of Application

Chaetocin is a natural metabolite isolated from Chaetomium minutum. It is a nonspecific inhbitor of histone lysine methyltransferases which are important epigenetic enzymes . Induces apoptosis in myeloma cell lines and exhibits antiproliferative activity in mammals. Chaetocin from Chaetomium minutum has been used to determine its effects on sensitization of various cells. It has also been used to determine the biological functions of OS-induced heterochromatin formation.

What are the applications of Application

Chaetocin is a lysine-specific histone methyltransferase inhibitor

General Description

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

Biochem/physiol Actions

Chaetocin is a competitive inhibitor for S-adenosylmethionine. The specificity of chaetocin for SU(VAR)3-9 makes this compound an excellent tool for the study of heterochromatin-mediated gene repression.

storage

-20°C

References

1) Greiner et al. (2005), Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9; Nat. Chem. Biol., 1 143
2) Isham et al. (2007), Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress; Blood, 109 2579

Properties of Chaetocin

Density  1.87±0.1 g/cm3(Predicted)
storage temp.  2-8°C
solubility  Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
pka 12.39±0.10(Predicted)
form  White to off-white solid
color  White
Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.

Safety information for Chaetocin

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P501:Dispose of contents/container to..…

Computed Descriptors for Chaetocin

InChIKey PZPPOCZWRGNKIR-PNVYSBBASA-N

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