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
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
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
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