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Merck
모든 사진(1)

문서

C9492

Sigma-Aldrich

Chaetocin from Chaetomium minutum

≥95% (HPLC)

동의어(들):

(+)-Chaetocin A

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About This Item

실험식(Hill 표기법):
C30H28N6O6S4
CAS Number:
Molecular Weight:
696.84
MDL number:
UNSPSC 코드:
12352202
PubChem Substance ID:
NACRES:
NA.77

Quality Level

분석

≥95% (HPLC)

형태

powder

저장 온도

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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관련 카테고리

일반 설명

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.

애플리케이션

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.

생화학적/생리학적 작용

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.

제조 메모

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

픽토그램

Exclamation mark

신호어

Warning

유해 및 위험 성명서

예방조치 성명서

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

dust mask type N95 (US), Eyeshields, Gloves


시험 성적서(COA)

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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
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Gardiner D M, et al.
Microbiology, 151(4), 1021-1032 (2005)
The molecular structure and absolute configuration of chaetocin
Weber H P
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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

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