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:
Molecular Weight:
710.87
MDL number:
UNSPSC Code:
41100000
NACRES:
NA.77
biological source
Chaetomium cochliodes
Quality Level
assay
≥98% (HPLC)
form
powder
solubility
DMSO: soluble, acetone: soluble, ethyl acetate: soluble
storage temp.
−20°C
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
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.
signalword
Danger
hcodes
pcodes
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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Instructions
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
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
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