Chaetocin

from Chaetomium minutum

Product Code C9492

Synonym: Chetocin
CAS Number: 28097-03-2
Molecular Formula : C₃₀H₂₈O₆N₆S₄
Molecular weight : 696.84

Chaetocin is a fungal metabolite with antimicrobial and cytostatic activity.^{1, 2} It belongs to the 3,6-epidithio-diketopiperazines class of which gliotoxin, sporidesmin, aranotin, oryzachloride, verticillin A and the melinacidins are members.^1,3 Chaetocin is a molecular dimer of two five-membered rings cis fused. ¹ Interestingly, the chirality of the 3,6-epidithio-diketopiperazine moiety in chaetocin is opposite to the chirality in gliotoxin, sporidesmin, aranotin and oryzachloride and while the later compounds show antiviral activity, chaetocin does not.¹ This fungal toxin showed strong cytotoxicity against HeLa cells (IC₅₀=0.05 µg/ml).²

Chaetocin was found to be a specific inhibitor of the lysine-specific histone methyltransferase SU(VAR)3-9 (IC₅₀= 0.6 µM) of Drosophila melanogaster and of its human ortholog (IC₅₀= 0.8 µM), and acts as a competitive inhibitor for S-adenosylmethionine.⁴ The specificity of chaetocin for SU(VAR)3-9 makes this compound an excellent tool for the study of heterochromatin-mediated gene repression.⁴

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

Storage/Stability
Store at 2-8 °C. Under these conditions the product is stable for 2 years.

References

1. Weber, H. P., et al., The molecular structure and absolute configuration of chaetocin. Acta Cryst., B28, 2945-2951 (1972).
2. Udagawa, S., et al., The production of chaetoglobosins, sterigmatocystin, O-methylsterigmatocystin, and chaetocin by Chaetomium spp. and related fungi. Can. J. microbiol., 25, 170-177 (1979).
3. Gardiner, D. M., et al., The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis. Microbiol., 151, 1021-1032 (2005).
4. Greiner, D., et al., Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9. Nat. Chem. Biol., 1, 143-145 (2005).

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