Chetomin

Specifications / Handling

More Information
Product Details
Synonyms	CTM; Chaetomin; NSC289491; BRN0077366
Product Type	Chemical
Properties
Formula	C₃₁H₃₀N₆O₆S₄
MW	710.9
CAS	1403-36-7
Source/Host Chemicals	Isolated from Chaetomium sp.
Purity Chemicals	≥90% (HPLC)
Appearance	Off-white to fawn solid.
Solubility	Soluble in DMSO, ethyl acetate or pyridine; fairly soluble in methanol or 100% ethanol; insoluble in water.
Identity	Determined by ¹H-NMR.
Declaration	Manufactured by BioViotica.
InChi Key	ZRZWBWPDBOVIGQ-OKMJTBRXSA-N
Smiles	[H][C@]12NC3=CC=CC=C3[C@]1(C[C@]13SS[C@@](CO)(N(C)C1=O)C(=O)N23)N1C=C(C[C@]23SS[C@@](CO)(N(C)C2=O)C(=O)N3C)C2=CC=CC=C12
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from moisture. Protect from light when in solution.
Use/Stability	Stable for at least 1 year after receipt when stored at -20°C. After reconstitution protect from light at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Anticancer antibiotic.
Inhibitor of HIF-1 formation by disrupting the binding of p300 to both HIF-1α and HIF-2α.
Histone H3K9 methyltransferases G9a and Suv39h inhibitor.
Tumor growth inhibitor.
Angiogenesis inhibitor.
Potent immunosuppressor.
Antibacterial and antifungal.
Strong inducer of retinal pigment epithelium (RPE).

Product References

The structure of chetomin: A.G. McInnes, et al.; JACS 98, 6741 (1976)
Effects of chetomin on growth and acidic fermentation products of rumen bacteria: W.C. Jen and G.A. Jones; Can. J. Microbiol. 29, 1399 (1983)
Immunomodulatory constituents from an Ascomycete, Chaetomiumseminudum: H. Fujimoto, et al.; J. Nat. Prod. 67, 98 (2004)
Small molecule blockade of transcriptional coactivation of the hypoxia-inducible factor pathway: A.L. Kung, et al.; Cancer Cell 6, 33 (2004)
Effects of HIF-1 inhibition by chetomin on hypoxia-related transcription and radiosensitivity in HT 1080 human fibrosarcoma cells: A. Staab, et al.; BMC Cancer 7, 213 (2007)
Epidithiodiketopiperazines block the interaction between hypoxia-inducible factor-1α (HIF-1α) and p300 by a zinc ejection mechanism: K.M. Cook, et al.; J. Biol. Chem. 284, 26831 (2009)
Direct inhibition of hypoxia-inducible transcription factor complex with designed dimeric epidithiodiketopiperazine: K. M. Wang, et al.; JACS 131, 18078 (2009)
Up-regulation of pro-inflammatory genes as adaptation to hypoxia in MCF-7 cells and in human mammary invasive carcinoma microenvironment: M. Tafani, et al.; Cancer Sci. 101, 1014 (2010)
Inhibition of histone H3K9 methyltransferases by gliotoxin and related epipolythiodioxopiperazines: M. Takahashi, et al., J. Antibiot. 65, 263 (2012)
Epidithiodiketopiperazines (ETPs) exhibit in vitro antiangiogenic and in vivo antitumor activity by disrupting the HIF-1α/p300 complex in a preclinical model of prostate cancer: K.M. Reece, et al.; Mol. Cancer 13, 91 (2014)
Small-molecule–directed, efficient generation of retinal pigment epithelium from human pluripotent stem cells: J. Maruotti, et al.; PNAS 112, 10950 (2015)
Chetomin, targeting HIF-1a/p300 complex, exhibits antitumour activity in multiple myeloma: E. Viziteu, et al.; Br. J. Canc. 114, 519 (2016)
Chetomin induces apoptosis in human triple-negative breast cancer cells by promoting calcium overload and mitochondrial dysfunction: J. Dewangan, et al.; BBRC 495, 1915 (2018)
Screening of a growth inhibitor library of sarcoma cell lines to identify potent anti-cancer drugs: Z. Qiao & T. Kondo; Electrophoresis 63, 1 (2019)
Chetomin, a Hsp90/HIF1a pathway inhibitor, effectively targets lung cancer stem cells and non-stem cells: S. Min, et al.; Cancer Biol. Ther. 21, 698 (2020)

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