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C9623

Chetomin

from Chaetomium cochliodes, ≥98% (HPLC)

Synonym(s):

Chaetomin, NSC 289491

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About This Item

Empirical Formula (Hill Notation):
C31H30N6O6S4
CAS Number:
1403-36-7
Molecular Weight:
710.87
MDL number:
MFCD28137713
UNSPSC Code:
41100000
NACRES:
NA.77

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SMILES string

S1SC9(N(C(=O)C1(N(C9=O)C)CO)C)Cc2c3c([n](c2)C54C(N7C8(SSC(N(C8=O)C)(C7=O)CO)C5)Nc6c4cccc6)cccc3

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

biological source

Chaetomium cochliodes

assay

≥98% (HPLC)

form

powder

solubility

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

storage temp.

−20°C

Quality Level

200

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1 of 4

This Item
T5580SML0301H1667
Sigma-Aldrich

Sigma-Aldrich

C9623

Chetomin

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

Sigma-Aldrich

T5580

Myxothiazol

Hymeglusin ≥98% (HPLC), from Fusarium sp.

Sigma-Aldrich

SML0301

Hymeglusin

Hypothemycin from Hypomyces trichothecoides, ≥98% (HPLC)

Sigma-Aldrich

H1667

Hypothemycin

form

powder

form

-

form

powder

form

-

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

DMSO: soluble, ethyl acetate: soluble, acetone: 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

DMSO: soluble, acetone: soluble, deionized water: insoluble

biological source

Chaetomium cochliodes

biological source

Myxococcus fulvus Mx f85

biological source

Fusarium sp.

biological source

Hypomyces trichothecoides

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.
Chetomin is a natural metabolite, which 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. Chetomin also suppresses the proliferation of LPS-induced mouse spleen lymphocytes.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
0000427374
0000427374
0000204999
0000395814
0000204999

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Rolf Spirig et al.
Molecular immunology, 46(15), 3178-3182 (2009-06-30)
Endothelin-1 (ET-1) is mainly secreted by endothelial cells and acts as a potent vasoconstrictor. In addition ET-1 has also been shown to have pleiotropic effects on a variety of other systems including adaptive immunity. There are two main ET-1 receptors
Huimin Lu et al.
The FEBS journal, 276(24), 7291-7304 (2009-11-17)
Aberrant differentiation is a characteristic feature of neoplastic transformation, while hypoxia in solid tumors is believed to be linked to aggressive behavior and poor prognosis. However, the possible relationship between hypoxia and differentiation in malignancies remains poorly defined. Here we
Adrian Staab et al.
BMC cancer, 7, 213-213 (2007-11-15)
Hypoxia-inducible factor-1 (HIF-1) overexpression has been linked to tumor progression and poor prognosis. We investigated whether targeting of HIF-1 using chetomin, a disrupter of the interaction of HIF-1 with the transcriptional coactivator p300, influences the radiosensitivity of hypoxic HT 1080
Manuela Indelicato et al.
Journal of cellular physiology, 223(2), 359-368 (2010-01-30)
Survival strategies adopted by tumor cells in response to a hypoxic stress include activation of hypoxia-inducible factor 1 (HIF-1) and autophagy. However, the importance and the function of each molecular response is not well defined. In the present study, we
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
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