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C9623

Sigma-Aldrich

Chetomin

from Chaetomium cochliodes, ≥98% (HPLC)

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Synonym(s):
Chaetomin, NSC 289491
Empirical Formula (Hill Notation):
C31H30N6O6S4
CAS Number:
1403-36-7
Molecular Weight:
710.87
NACRES:
NA.77

biological source

Chaetomium cochliodes

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: soluble
acetone: soluble
ethyl acetate: soluble

storage temp.

−20°C

InChI

1S/C31H30N6O6S4/c1-33-25(42)30(15-38)34(2)23(40)28(33,44-46-30)12-17-13-36(21-11-7-4-8-18(17)21)27-14-29-24(41)35(3)31(16-39,47-45-29)26(43)37(29)22(27)32-20-10-6-5-9-19(20)27/h4-11,13,22,32,38-39H,12,14-16H2,1-3H3

InChI key

ZRZWBWPDBOVIGQ-UHFFFAOYSA-N

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C9623

Chetomin

Myxothiazol from Myxococcus fulvus Mx f85, ≥98% (HPLC)

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Hymeglusin

Caffeic acid phenethyl ester ≥97% (HPLC), powder

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form

powder

form

-

form

powder

form

powder

solubility

DMSO: soluble, acetone: soluble, ethyl acetate: soluble

solubility

chloroform: soluble 9.80-10.20 mg/mL, clear, colorless to yellow, DMSO: soluble, acetone: soluble, dichloromethane: soluble, ethanol: soluble, ethyl acetate: soluble, methanol: soluble

solubility

DMSO: soluble, H2O: insoluble, acetone: soluble, chloroform: soluble, ethyl acetate: soluble

solubility

ethyl acetate: 50 mg/mL, DMSO: soluble, ethanol: soluble

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

-

biological source

Chaetomium cochliodes

biological source

Myxococcus fulvus Mx f85

biological source

Fusarium sp.

biological source

synthetic

Biochem/physiol Actions

Chetomin is a natural metabolite produced by several species of the genus Chaetomium. Chetomin disrupts the hypoxia-inducible factor (HIF) pathway, blockomg the interaction of HIF1α and HIF2α with transcriptional co-activators p300 and cAMP response element binding (CREB) binding protein (CBP), thereby attenuating hypoxia-inducible transcription. Disrupting the ability of tumors to adapt to hypoxia leads to decreased tumor growth; hypoxia can also promote resistance to radiotherapeutics. By both of these mechanisms, chetomin shows promise as a lead compound in antitumor research. Chetomin also suppresses the proliferation of LPS-induced mouse spleen lymphocytes.
Chetomin is a natural metabolite produced by several species of the genus Chaetomium. Chetomin is an epidithiodioxopiperazine known to disrupt the hypoxia-inducible factor (HIF) pathway. Chetomin blocks the interaction of HIF1α and HIF2α with transcriptional co-activators p300 and cAMP response element binding (CREB) binding protein (CBP), thereby attenuating hypoxia-inducible transcription. Disrupting the ability of tumors to adapt to hypoxia leads to decreased tumor growth and can serve as an antitumor stratagy. Chetomin also suppresses the proliferation of LPS-induced mouse spleen lymphocytes.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Zhi-Jun Wu et al.
Analytical chemistry, 80(1), 217-226 (2007-12-07)
A series of epipolythiodioxopiperazines in the fungus Chaetomium cochliodes was investigated using reversed-phase liquid chromatography with diode array detection and electrospray quadrupole time-of-flight-type tandem mass spectrometry in the positive ion mode. The fragmentation of protonated molecular ions including low-abundance parent
M Sugiyama et al.
Biochemical and biophysical research communications, 271(3), 688-692 (2000-05-18)
Bone morphogenetic protein (BMP)-2, a member of the BMP family, plays an important role in osteoblast differentiation and bone formation. To discover small molecules that induce BMP-2, a luciferase reporter vector containing the 5'-flanking promoter region of the human BMP-2
S Sekita et al.
Canadian journal of microbiology, 27(8), 766-772 (1981-08-01)
Screening for mycotoxin production by Chaetomium spp. and related fungi on rice culture was conducted by a combination of cytotoxicity tests using HeLa cells and thin-layer chromatography. Producers of sterigmatocystin, O-methylsterigmatocystin, chaetochromin, chaetocin, chetomin, cochliodinols, and mollicellin G were found
Laura K Henchey et al.
Journal of the American Chemical Society, 132(3), 941-943 (2010-01-01)
Designed ligands that inhibit hypoxia-inducible gene expression could offer new tools for genomic research and, potentially, drug discovery efforts for the treatment of neovascularization in cancers. We report a stabilized alpha-helix designed to target the binding interface between the C-terminal
Kimihiro Yano et al.
International journal of oncology, 38(2), 365-374 (2010-12-18)
Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is one of the most promising anti-cancer agents, but some tumor types develop resistance to TRAIL. Here, we report that chetomin, an inhibitor of hypoxia-inducible factors, is a potent enhancer of TRAIL-induced apoptosis. TRAIL
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