28097-03-2

Basic information

• Product Name: CHAETOCIN FROM CHAETOMIUM MINUTUM
• Synonyms: chetocin;CHAETOCIN FROM CHAETOMIUM MINUTUM;CHAETOCIN(SH);(3S,3'S,5aR,5'aR,10bR,10'bR,11aS,11'aS)-2,2',3,3',5a,5'a,6,6'-Octahydro-3,3'-bis(hydroxymethyl)-2,2'-dimethyl-[10b,10'b(11H,11'H)-bi-3,11a-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone;Chaetocin A;[10b,10'b(11H,11'H)-Bi-3,11a-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone,2,2',3,3',5a,5'a,6,6'-octahydro-3,3'-bis(hydroxymethyl)-2,2'-dimethyl-,(3S,3'S,5aR,5'aR,10bR,10'bR,11aS,11'aS)-;HMTase Inhibitor II, Chaetocin;(3S,3'S,6R,6'R,14R,14'R,16S,16'S)-3,3'-bis(hydroxymethyl)-2,2'-dimethyl-2,2',3,3',6,6',7,7'-octahydro-1H,1'H-[14,14'-bi(3,11a-epidithiopyrazino[1',2':1,5]pyrrolo[2,3-b]indole)]-1,1',4,4'(15H,15'H)-tet
• CAS NO: 28097-03-2
• Molecular Formula: C30H28N6O6S4
• Molecular Weight: 696.851
• EINECS: 200-258-5
• Product Categories: Miscellaneous Enzyme
• Mol File: 28097-03-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.87g/cm³
• Refractive Index: 1.93
• 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)
• 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.
• CAS DataBase Reference: CHAETOCIN FROM CHAETOMIUM MINUTUM(CAS DataBase Reference)
• NIST Chemistry Reference: CHAETOCIN FROM CHAETOMIUM MINUTUM(28097-03-2)
• EPA Substance Registry System: CHAETOCIN FROM CHAETOMIUM MINUTUM(28097-03-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• RIDADR: 1544
• WGK Germany: 3
• RTECS: FM3032000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 28097-03-2(Hazardous Substances Data)

Usage

Description

Chaetocin from Chaetomium minutum is an antimicrobial fungal metabolite belonging to the 3,6-epidithio-diketopiperazines class. It is a molecular dimer of two five-membered rings cis fused and exhibits antimicrobial and cytostatic activity. Chaetocin is a potent inhibitor of lysine-specific methyltransferase SU(VAR)3-9, both in vitro and in vivo, and is known for its strong cytotoxicity against HeLa cells. It is also a specific inhibitor of the lysine-specific histone methyltransferase SU(VAR)3-9 of Drosophila melanogaster and its human ortholog, acting as a competitive inhibitor for S-adenosylmethionine. Chaetocin has an antimyeloma activity linked to the induction of oxidative stress and subsequent apoptosis.

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 this compound 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

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

Relevant articles and documents

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

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