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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:
28097-03-2
Peso molecular:
696.84
MDL number:
MFCD00133163
UNSPSC Code:
12352202
PubChem Substance ID:
24893002
NACRES:
NA.77

Quality Level

200

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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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
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Sophie Bouchat et al.
AIDS (London, England), 26(12), 1473-1482 (2012-05-05)
Reactivation of HIV-1 expression in persistent reservoirs together with an efficient HAART has been proposed as an adjuvant therapy aimed at reaching a functional cure for HIV. Previously, H3K9 methylation was shown to play a major role in chromatin-mediated repression
Jennifer D Tibodeau et al.
Antioxidants & redox signaling, 11(5), 1097-1106 (2008-11-13)
We recently reported that the antineoplastic thiodioxopiperazine natural product chaetocin potently induces cellular oxidative stress, thus selectively killing cancer cells. In pursuit of underlying molecular mechanisms, we now report that chaetocin is a competitive and selective substrate for the oxidative
The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis
Gardiner D M, et al.
Microbiology, 151(4), 1021-1032 (2005)
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)
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