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Merck

C9492

Sigma-Aldrich

Chaetocin from Chaetomium minutum

≥95% (HPLC)

Sinónimos:

(+)-Chaetocin A

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About This Item

Fórmula empírica (notación de Hill):
C30H28N6O6S4
Número de CAS:
Peso molecular:
696.84
Número MDL:
Código UNSPSC:
12352202
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

Análisis

≥95% (HPLC)

formulario

powder

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

PZPPOCZWRGNKIR-UHFFFAOYSA-N

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Descripción general

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.

Aplicación

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.

Acciones bioquímicas o fisiológicas

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.

Nota de preparación

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

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Acute Tox. 4 Oral

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

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)
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
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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