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Merck
CN

C9623

Sigma-Aldrich

黑毛霉素

from Chaetomium cochliodes, ≥98% (HPLC)

别名:

Chaetomin, NSC 289491

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About This Item

经验公式(希尔记法):
C31H30N6O6S4
CAS号:
分子量:
710.87
MDL编号:
UNSPSC代码:
41100000
NACRES:
NA.77

生物来源

Chaetomium cochliodes

质量水平

方案

≥98% (HPLC)

表单

powder

溶解性

DMSO: soluble
acetone: soluble
ethyl acetate: soluble

储存温度

−20°C

SMILES字符串

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

生化/生理作用

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.

象形图

Skull and crossbones

警示用语:

Danger

危险声明

预防措施声明

危险分类

Acute Tox. 3 Oral

储存分类代码

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number

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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
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
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
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

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