C9492

Chaetocin from Chaetomium minutum

≥95% (HPLC)

• Synonym(s): (+)-Chaetocin A
• Empirical Formula (Hill Notation): C₃₀H₂₈N₆O₆S₄
• CAS Number: 28097-03-2
• Molecular Weight: 696.84
• NACRES: NA.77
• PubChem Substance ID: 24893002
• UNSPSC Code: 12352202
• MDL number: MFCD00133163
• Assay: ≥95% (HPLC)
• Form: powder

Properties

• Quality Segment: 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

Description

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

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

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.

Preparation Note

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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves