C9492

Chaetocin aus Chaetomium minutum

≥95% (HPLC)

• Synonym(e): (+)-Chaetocin A
• Empirische Formel (Hill-System): C₃₀H₂₈N₆O₆S₄
• CAS-Nummer: 28097-03-2
• Molekulargewicht: 696.84
• NACRES: NA.77
• PubChem Substance ID: 24893002
• UNSPSC Code: 12352202
• MDL number: MFCD00133163
• Assay: ≥95% (HPLC)
• Form: powder

Eigenschaften

• 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

Beschreibung

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.[1]

Biochem/physiol Actions

Methyltransferase making the compound useful in the study of heterochromatin mediated gene repression.[2]

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.[2] Chaetocin is a selective competitive inhibitor of thioredoxin reductase-1 (TrxR1), a putative mechanism of its anticancer activity.[3]

Preparation Note

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

Sicherheitshinweise

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