Direkt zum Inhalt
Merck
Alle Fotos(1)

Key Documents

Weitere Dokumente

C9492

Sigma-Aldrich

Chaetocin aus Chaetomium minutum

≥95% (HPLC)

Synonym(e):

(+)-Chaetocin A

Anmeldenzur Ansicht organisationsspezifischer und vertraglich vereinbarter Preise
Alle Fotos(1)

About This Item

Empirische Formel (Hill-System):
C30H28N6O6S4
CAS-Nummer:
28097-03-2
Molekulargewicht:
696.84
MDL-Nummer:
MFCD00133163
UNSPSC-Code:
12352202
PubChem Substanz-ID:
24893002
NACRES:
NA.77

Qualitätsniveau

200

Assay

≥95% (HPLC)

Form

powder

Lagertemp.

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

InChIKey

PZPPOCZWRGNKIR-UHFFFAOYSA-N

Suchen Sie nach ähnlichen Produkten? Aufrufen Leitfaden zum Produktvergleich

Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

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.

Angaben zur Herstellung

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

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

Besitzen Sie dieses Produkt bereits?

In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

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)
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
Justin Kim et al.
Journal of the American Chemical Society, 132(41), 14376-14378 (2010-09-28)
A highly stereoselective and systematic strategy for the introduction of polysulfides in the synthesis of epipolythiodiketopiperazines is described. We report the first total synthesis of dimeric epitri- and epitetrathiodiketopiperazines.
Identification of a specific inhibitor of the histone methyltransferase SU (VAR) 3-9
Greiner D, et al.
Nature Chemical Biology, 1(3), 143-143 (2005)
Yoon-Mi Lee et al.
Hepatology (Baltimore, Md.), 53(1), 171-180 (2010-12-09)
Chaetocin, an antibiotic produced by Chaetomium species fungi, was recently found to have antimyeloma activity. Here we examined whether chaetocin has anticancer activities against solid tumors. Chaetocin inhibited the growth of mouse and human hepatoma grafts in nude mice. Immunohistochemical
Alle zugehörigen Dokumente anzeigen

Artikel

Histone Modification and Chromatin Remodeling | Epigenetics

Epigenetic modifications are thought to occur through two key interconnected processes—DNA methylation and the covalent modification of histones.

Unser Team von Wissenschaftlern verfügt über Erfahrung in allen Forschungsbereichen einschließlich Life Science, Materialwissenschaften, chemischer Synthese, Chromatographie, Analytik und vielen mehr..

Setzen Sie sich mit dem technischen Dienst in Verbindung.