28097-03-2

Usage

Uses

Used in Anticancer Applications:
Chaetocin from Chaetomium minutum is used as an antitumor agent for its selective action against cancer cells. It has shown promise in inhibiting the growth and progression of various types of cancer, including solid malignancies, by modulating oncological signaling pathways and inducing apoptosis.
Used in Epigenetic Research:
Chaetocin is used as a specific inhibitor of the lysine-specific histone methyltransferase SU(VAR)3-9, making it an excellent tool for studying heterochromatin-mediated gene repression and the biological functions of oxidative stress-induced heterochromatin formation.
Used in Drug Development:
Chaetocin from Chaetomium minutum is used as a nonspecific inhibitor of histone lysine methyltransferases, which are important epigenetic enzymes. Its ability to induce apoptosis in myeloma cell lines and exhibit antiproliferative activity in mammals makes it a valuable compound in the development of new drugs for cancer treatment and other applications.
Used in Cellular Sensitization Studies:
Chaetocin has been used to determine its effects on the sensitization of various cells, providing insights into its potential applications in enhancing the sensitivity of cells to certain treatments or conditions.
Used in Pharmaceutical Industry:
Chaetocin from Chaetomium minutum is used as a raw material in the development of new drugs and therapies, particularly in the field of cancer treatment and epigenetic research. Its unique properties and mechanisms of action make it a promising candidate for further investigation and application in the pharmaceutical industry.

Biochem/physiol Actions

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

References

1) Greiner et al. (2005), Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9; Nat. Chem. Biol., 1 1432) 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

InChI:InChI=1/C30H28N6O6S4/c1-33-21(39)27-11-25(15-7-3-5-9-17(15)31-19(25)35(27)23(41)29(33,13-37)45-43-27)26-12-28-22(40)34(2)30(14-38,46-44-28)24(42)36(28)20(26)32-18-10-6-4-8-16(18)26/h3-10,19-20,31-32,37-38H,11-14H2,1-2H3

Upstream product

• 1219135-51-9 C₅₂H₇₆N₆O₁₄Si₂ 
• 1219135-73-5 C₅₂H₇₆N₆O₁₄Si₂ 
• 28097-04-3 (+)-chaetocin A diacetate 
• 118111-08-3 chaetocin C 
• 118101-82-9 chaetocin B 

Relevant academic research and scientific papers

Epidithiodiketopiperazine as a pharmacophore for protein lysine methyltransferase G9a inhibitors: Reducing cytotoxicity by structural simplification

Chaetocin (1), a structurally complex epidithiodiketopiperazine (ETP) alkaloid produced by Chaetomium minutum, is a potent inhibitor of protein lysine methyltransferase G9a, which plays important roles in many biological processes. Here we present our syn

General approach to epipolythiodiketopiperazine alkaloids: Total synthesis of (+)-chaetocins A and C and (+)-12,12′-dideoxychetracin A

A highly stereoselective and systematic strategy for the introduction of polysulfides in the synthesis of epipolythiodiketopiperazines is described. We report the first total synthesis of dimeric epitri- and epitetrathiodiketopiperazines.

Total synthesis of (+)-chaetocin and its analogues: Their histone methyltransferase g9a inhibitory activity

Chemical Equation Presentation The first total synthesis of (+)-chaetorin has been accomplished in only nine steps starting from the known N-Cbz-N-Me-serie using radical α-bromlnatlon reaction of diketopiperazine 10 and Co(I)-mediated reductive dimerizati