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Merck

C9492

Sigma-Aldrich

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
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

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

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1 of 4

This Item
C9623T4540F6771
Sigma-Aldrich

C9623

Chetomin

form

powder

form

powder

form

powder

form

powder

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

General description

Chaetocin is a fungal metabolite with antimicrobial and cytostatic activity.[1] It belongs to the 3,6-epidithio-diketopiperazines class[2] of which gliotoxin, sporidesmin, aranotin, oryzachloride, verticillin A and the melinacidins are members.[3] 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.[4] It has also been used to determine the biological functions of OS-induced heterochromatin formation.[5]

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.[2]
Chaetocin is an antibacterial mycotoxin.[6] It is a specific inhibitor of lysine-specific histone methyltransferase making the compound useful in the study of heterochromatin mediated gene repression.[7] Chaetocin is a selective competitive inhibitor of thioredoxin reductase-1 (TrxR1), a putative mechanism of its anticancer activity.[8]
Methyltransferase making the compound useful in the study of heterochromatin mediated gene repression.[7]

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

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
Romains Joubert et al.
Journal of personalized medicine, 11(1) (2020-12-31)
Facioscapulohumeral dystrophy (FSHD, OMIM: 158900, 158901) is the most common dystrophy in adults and so far, there is no treatment. Different loci of the disease have been characterized and they all lead to the aberrant expression of the DUX4 protein
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)
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)
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

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