C9492

Sigma-Aldrich

Chaetocin from Chaetomium minutum

≥95% (HPLC)

Empirical Formula (Hill Notation):
C30H28N6O6S4
CAS Number:
Molecular Weight:
696.84
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

assay

≥95% (HPLC)

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

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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

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.
Methyltransferase making the compound useful in the study of heterochromatin mediated gene repression.

Preparation Note

Soluble in DMSO. At 1 mg/ml the solution is stable for 1 week at 2-8 °C.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Heterochromatin protects retinal pigment epithelium cells from oxidative damage by silencing p53 target genes
Gong L, et al.
Proceedings of the National Academy of Sciences of the USA, 115(17), E3987-E3995 (2018)
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...
The molecular structure and absolute configuration of chaetocin
Weber H P
Acta Crystallographica Section B, Structural Crystallography and Crystal Chemistry, 28(10), 2945-2951 (1972)
Hyun Seung Ban et al.
Expert opinion on therapeutic patents, 21(2), 131-146 (2011-01-08)
Hypoxia-inducible factor (HIF) is a heterodimeric transcription factor consisting of α and β subunits that regulates the expression of angiogenic factors, including VEGF, which are involved in angiogenesis, invasion/metastasis, glucose uptake and cell survival during cancer development. This review summarizes...
Xiao-Gang Weng et al.
Theriogenology, 146, 162-170 (2019-12-04)
Aberrant epigenetic reprogramming is a major cause of the developmental failure of embryos after somatic cell nuclear transfer (SCNT). Histone H3 lysine 9 trimethylation (H3K9me3), a histone marker of transcriptional repression, is considered a key barrier to the development of...
Articles
Epigenetic modifications are thought to occur through two key interconnected processes—DNA methylation and the covalent modification of histones.
Read More

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