Skip to Content
MilliporeSigma

C9492

Chaetocin from Chaetomium minutum

≥95% (HPLC)

Synonym(s):

(+)-Chaetocin A

Slide 1 of 1
Sign In to View Organizational & Contract Pricing.

Select a Size

1 MG

$454.00

$454.00

Available to ship TODAYDetails

About This Item

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

Key Documents

View All Documentation

Skip To

Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Chaetocin from Chaetomium minutum, ≥95% (HPLC)

InChI key

PZPPOCZWRGNKIR-UHFFFAOYSA-N

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

assay

≥95% (HPLC)

form

powder

storage temp.

2-8°C

Quality Level

200

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
C9623T4540F6771
Chaetocin from Chaetomium minutum ≥95% (HPLC)

Sigma-Aldrich

C9492

Chaetocin from Chaetomium minutum

Sigma-Aldrich

Sigma-Aldrich

C9623

Chetomin

Triacsin C from Streptomyces sp.

Sigma-Aldrich

T4540

Triacsin C from Streptomyces sp.

Fumagillin from Aspergillus fumigatus ≥90%, powder

Sigma-Aldrich

F6771

Fumagillin from Aspergillus fumigatus

form

powder

form

powder

form

powder

form

powder

assay

≥95% (HPLC)

assay

≥98% (HPLC)

assay

-

assay

≥90%

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Preparation Note

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

Application

Chaetocin from Chaetomium minutum has been used to determine its effects on sensitization of various cells.[1] It has also been used to determine the biological functions of OS-induced heterochromatin formation.[2]

Biochem/physiol Actions

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.[3]
Chaetocin is an antibacterial mycotoxin.[4] It is a specific inhibitor of lysine-specific histone methyltransferase making the compound useful in the study of heterochromatin mediated gene repression.[5] Chaetocin is a selective competitive inhibitor of thioredoxin reductase-1 (TrxR1), a putative mechanism of its anticancer activity.[6]
Methyltransferase making the compound useful in the study of heterochromatin mediated gene repression.[5]

General description

Chaetocin is a fungal metabolite with antimicrobial and cytostatic activity.[7] It belongs to the 3,6-epidithio-diketopiperazines class[3] of which gliotoxin, sporidesmin, aranotin, oryzachloride, verticillin A and the melinacidins are members.[8] Chaetocin is a molecular dimer of two five-membered rings cis fused.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000510796
0000510796
0000458760
0000458760
0000239131

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Sophie Bouchat et al.
AIDS (London, England), 26(12), 1473-1482 (2012-05-05)
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
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)
Crescent R Isham et al.
Blood, 109(6), 2579-2588 (2006-11-09)
Chaetocin, a thiodioxopiperazine natural product previously unreported to have anticancer effects, was found to have potent antimyeloma activity in IL-6-dependent and -independent myeloma cell lines in freshly collected sorted and unsorted patient CD138(+) myeloma cells and in vivo. Chaetocin largely
View All Related Papers

Related Content

Data Sheet - C9492

Instructions

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service