C9623

Chetomin

Name: Chetomin
Brand: SIGMA

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

Product Name

Chetomin, from Chaetomium cochliodes, ≥98% (HPLC)

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

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

GHS06

signalword

Danger

hcodes

H301

pcodes

P301 + P310

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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Lot/Batch Number

0000427374

0000395814

0000216563

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TLR2 and TLR4 agonists induce production of the vasoactive peptide endothelin-1 by human dendritic cells.

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

Role of hypoxia and autophagy in MDA-MB-231 invasiveness.

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

Compactin and simvastatin, but not pravastatin, induce bone morphogenetic protein-2 in human osteosarcoma cells.

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

Chetomin induces degradation of XIAP and enhances TRAIL sensitivity in urogenital cancer cells.

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

Mycotoxin production by Chaetomium spp. and related fungi.

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

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