Chaetocin

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Chaetocin

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Cat No: 13156

Biochemicals - Small Molecule Inhibitors

The methylation of histones by histone methyltransferases (HMT) is an important mechanism by which gene expression is stably altered during cellular differentiation and embryonic development. Chaetocin is a fungal mycotoxin that inhibits the HMT SU(VAR...

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Territorial Availability: Available through Bertin Technologies only in France

                                            Technical Warning: Bertin Technologies restricts the sale of this product to licensed controlled substance laboratories and qualified academic research institutions. Please contact us for further details.
                    

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Synonyms:

2,2',3S,3'S,5aR,5'aR,6,6'-octahydro-3,3'-bis(hydroxymethyl)-2,2'-dimethyl-[10bR,10'bR(11aS,11'aS)-bi-3,11a-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone

Correlated keywords:

histones methyltransferases HMTs genes expressions epigenetics inhibitors oxidative stress cancers theoredoxin reductase-1 TrxR1 inhibits inhibition chetocin chaetocin A (+)-chaetocin piperazines regulations

Product Overview:
The methylation of histones by histone methyltransferases (HMT) is an important mechanism by which gene expression is stably altered during cellular differentiation and embryonic development. Chaetocin is a fungal mycotoxin that inhibits the HMT SU(VAR)3-9 (IC50 = 0.8 μM).{18476} It inhibits other Lys9-specific HMTs, including G9a (IC50 = 2.5 μM) and DIM5 (IC50 = 3 μM).{18476} Selectivity for Lys9-HMTs is indicated by higher IC50 values (>90 μM) for Lys20-specific PRSET7, Lys27-specific EZH2, and Lys4-specific SET7/9. Chaetocin potently induces cellular oxidative stress, selectively killing cancer cells and rapidly-proliferating primary cells.{18475,18476} Chaetocin’s effects on oxidative stress are, at least in part, due to its capacity to act as a competitive and selective substrate for thioredoxin reductase-1 (Km = 4.6 μM).{18477} Chaetocin is useful both in epigenetic studies as an HMT inhibitor and in cancer research.{18398,17782,18480}

Size	500 µg
Shipping	dry ice
CAS Number	28097-03-2
Molecular Formula	C₃₀H₂₈N₆O₆S₄
SMILES	O=C1[C@](CO)(SS2)N(C)C([C@]32N1[C@@H](NC4=CC=CC=C45)[C@]5([C@@]6(C7=CC=CC=C7N8)[C@H]8N(C([C@](CO)(SS9)N(C)C%10=O)=O)[C@]%109C6)C3)=O
Molecular Weight	696,8
Formulation	A crystalline solid
Purity	≥95%
Custom Code	2933.49
UNSPSC code	12352100

Technical File

MSDS

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Cayman Chemical's mission is to help make research possible by supplying scientists worldwide with the basic research tools necessary for advancing human and animal health. Our utmost commitment to healthcare researchers is to offer the highest quality products with an affordable pricing policy.

Our scientists are experts in the synthesis, purification, and characterization of biochemicals ranging from small drug-like heterocycles to complex biolipids, fatty acids, and many others. We are also highly skilled in all aspects of assay and antibody development, protein expression, crystallization, and structure determination.

Over the past thirty years, Cayman developed a deep knowledge base in lipid biochemistry, including research involving the arachidonic acid cascade, inositol phosphates, and cannabinoids. This knowledge enabled the production of reagents of exceptional quality for cancer, oxidative injury, epigenetics, neuroscience, inflammation, metabolism, and many additional lines of research.

Our organic and analytical chemists specialize in the rapid development of manufacturing processes and analytical methods to carry out clinical and commercial GMP-API production. Pre-clinical drug discovery efforts are currently underway in the areas of bone restoration and repair, muscular dystrophy, oncology, and inflammation. A separate group of Ph.D.-level scientists are dedicated to offering Hit-to-Lead Discovery and Profiling Services for epigenetic targets. Our knowledgeable chemists can be contracted to perform complete sample analysis for analytes measured by the majority of our assays. We also offer a wide range of analytical services using LC-MS/MS, HPLC, GC, and many other techniques.

Accreditations
ISO/IEC 17025:2005
ISO Guide 34:2009

Cayman is a leader in the field of emerging drugs of abuse, providing high-purity Schedule I-V Controlled Substances to federally-licensed laboratories and qualified academic research institutions for forensic analyses. We are certified by ACLASS Accreditation Services with dual accreditation to ISO/IEC 17025:2005 and ISO Guide 34:2009.