| Identification | Back Directory | [Name]
CHAETOCIN FROM CHAETOMIUM MINUTUM | [CAS]
28097-03-2 | [Synonyms]
chetocin
Chaetocin A
CHAETOCIN(SH)
Chaetocin, from fungus
Chaetocin, 98%, from fungus
HMTase Inhibitor II, Chaetocin
CHAETOCIN FROM CHAETOMIUM MINUTUM
CHAETOCIN FROM CHAETOMIUM MINUTUM USP/EP/BP
Chaetocin from Chaetomium minutum >=95% (HPLC)
HMTase Inhibitor II, Chaetocin - CAS 28097-03-2 - Calbiochem
(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
(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
[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)- | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C30H28N6O6S4 | [MDL Number]
MFCD00133163 | [MOL File]
28097-03-2.mol | [Molecular Weight]
696.851 |
| Chemical Properties | Back Directory | [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). | [form ]
White to off-white solid | [pka]
12.39±0.10(Predicted) | [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. | [InChIKey]
PZPPOCZWRGNKIR-PNVYSBBASA-N | [SMILES]
CN1C(=O)C23CC4(C(Nc5ccccc45)N2C(=O)C1(CO)SS3)C67CC89SSC(CO)(N(C)C8=O)C(=O)N9C6Nc%10ccccc7%10 |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P264-P270-P301+P312-P501 | [Hazard Codes ]
Xn | [Risk Statements ]
20/21/22 | [RIDADR ]
1544 | [WGK Germany ]
3 | [RTECS ]
FM3032000 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29419090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Description]
Chaetocin (28097-69-1) is an antimicrobial fungal metabolite. Selective inhibitor of lysine specific histone methytransferase.1 Chaetocin has an antimyeloma activity which has been linked to induction of oxidative stress and subsequent apoptosis.2 | [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. | [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. | [Uses]
Chaetocin is an epithiodioxopiperazine antibiotic that has recently shown promise as a selective antitumor 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. | [Uses]
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. | [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. | [Biological Activity]
Chaetocin, an antitumor antibiotic, is a thiodioxopiperazine natural product produced by Chaetomium species. Specific inhibitor of the lysine-specific methyltransferase SU (VAR)3-9 both in vitro and in vivo. It displays potent antimyeloma activity in IL-6-dependent myeloma cell lines. Its antimyeloma activity appears to be due to induction of oxidative stress and consequent apoptosis. | [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]
Store at -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 |
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