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C9623

Sigma-Aldrich

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
UNSPSC Code:
12352200
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

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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
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
Chetomin an antibiotic substance from Chaetomium cochliodes; composition and functional groups.
W B GEIGER
Archives of biochemistry, 21(1), 125-131 (1949-03-01)
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