C9492
Chaetocin from Chaetomium minutum
≥95% (HPLC)
Synonym(s):
(+)-Chaetocin A
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About This Item
Empirical Formula (Hill Notation):
C30H28N6O6S4
CAS Number:
Molecular Weight:
696.84
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
MDL number:
Quality Level
assay
≥95% (HPLC)
form
powder
storage temp.
2-8°C
SMILES string
CN1C(=O)C23CC4(C(Nc5ccccc45)N2C(=O)C1(CO)SS3)C67CC89SSC(CO)(N(C)C8=O)C(=O)N9C6Nc%10ccccc7%10
InChI
1S/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
InChI key
PZPPOCZWRGNKIR-UHFFFAOYSA-N
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.
Application
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.
Biochem/physiol Actions
Methyltransferase making the compound useful in the study of heterochromatin mediated gene repression.
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.
Chaetocin is an antibacterial mycotoxin. It is a specific inhibitor of lysine-specific histone methyltransferase making the compound useful in the study of heterochromatin mediated gene repression. Chaetocin is a 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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Related Content
Instructions
Dorothea Greiner et al.
Nature chemical biology, 1(3), 143-145 (2006-01-13)
Histone methylation plays a key role in establishing and maintaining stable gene expression patterns during cellular differentiation and embryonic development. Here, we report the characterization of the fungal metabolite chaetocin as the first inhibitor of a lysine-specific histone methyltransferase. Chaetocin
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Gong L, et al.
Proceedings of the National Academy of Sciences of the USA, 115(17), E3987-E3995 (2018)