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Description: SUV39H1 inhibitor
Chemical Name: (3S,3'S,5aR,5aR,10bR,10'bR,11aS,11'aS)-2,2',3,3',5a,5'a,6,6'-octahydro-3,3'-bis(hydroxymethyl)-2,2'-dimethyl-[10b,10'b(11H,11'H)-bi3,11a-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone
Purity: ≥95% (HPLC)
Biological Activity for Chaetocin
Chaetocin is a histone methyltransferase SUV39H1 inhibitor (IC50 values are 0.8, 2.5 and 3 μM for dSU(VAR)3-9, mouse G9a and Neurospora crassa DIM5, respectively). Induces apoptosis in myeloma cell lines in vitro; exhibits antiproliferative activity in a mouse myeloma model in vivo.
Chaetocin potently inhibits cell proliferation and colony formation in a wide range of cancer cell lines (IC50 of 2-10 nM) and inhibits tumor growth by deregulating HIF-1α-mediated angiogenesis. Sensitizes glioblastoma multiforme cells to pro-apoptotic agents.
Chaetocin is also an inhibitor of the oxidative stress remediation enzyme thioredoxin reductase (TrxR), and so induces oxidative stress.
In addition, Chaetocin promotes osteogenic differentiation through modulating Wnt/Beta-catenin signaling in mesenchymal stem cells. Chaetocin treatment increased osteogenic ability and reduced adipogenic ability.
Technical Data for Chaetocin
| M. Wt | 696.84 |
| Formula | C30H28N6O6S4 |
| Storage | Store at -20°C |
| Purity | ≥95% (HPLC) |
| CAS Number | 28097-03-2 |
| PubChem ID | 161591 |
| InChI Key | PZPPOCZWRGNKIR-UHFFFAOYSA-N |
| Smiles | [H][C@]12NC3=C(C=CC=C3)[C@]1(C[C@]13SS[C@](CO)(N(C)C1=O)C(=O)N23)[C@]12C[C@]34SS[C@](CO)(N(C)C3=O)C(=O)N4[C@@]1([H])NC1=C2C=CC=C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Chaetocin
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 6.97 | 10 |
Preparing Stock Solutions for Chaetocin
The following data is based on the product molecular weight 696.84. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.1 mM | 14.35 mL | 71.75 mL | 143.5 mL |
| 0.5 mM | 2.87 mL | 14.35 mL | 28.7 mL |
| 1 mM | 1.44 mL | 7.18 mL | 14.35 mL |
| 5 mM | 0.29 mL | 1.44 mL | 2.87 mL |
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Product Datasheets for Chaetocin
References for Chaetocin
References are publications that support the biological activity of the product.
Isham et al (2007) Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress. Blood 109 2579 PMID: 17090648
Greiner et al (2005) Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9. Nat.Chem.Biol. 1 143 PMID: 16408017
Cherblanc et al (2013) Chaetocin is a nonspecific inhibitor of histone lysine methyltransferases. Nat.Chem.Biol. 9 136 PMID: 23416387
Greiner et al (2013) Reply to "Chaetocin is a nonspecific inhibitor of histone lysine methyltransferases". Nat.Chem.Biol. 9 137 PMID: 23416388
Ozyerli-Goknar et al (2019) The fungal metabolite chaetocin is a sensitizer for pro-apoptotic therapies in glioblastoma. Cell Death Dis 10 894 PMID: 31772153
Liang et al (2021) Chaetocin Promotes Osteogenic Differentiation via Modulating Wnt/Beta-Catenin Signaling in Mesenchymal Stem Cells. Stem Cells Int. doi: 10.1155/2021/88 PMID: 33628276
Nakajima et al (2017) Inhibition of the HDAC/Suv39/G9a pathway restores the expression of DNA damage-dependent major histocompatibility complex class I-related chain A and B in cancer cells. Oncol Rep. 38 693 PMID: 28677817
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Keywords: Chaetocin, Chaetocin supplier, histone, lysine, methyltransferase, HMTase, SUV39H1, su(var)3-9, epigenetics, inhibits, inhibitors, antiproliferative, myeloma, selective, G9a, glioblastoma, thioredoxin, reductases, bone, osteogenic, stem, cell, differentiation, Lysine, Methyltransferases, Other, Osteogenic, Stem, Cells, Thioredoxin, Reductases, 4504, Tocris Bioscience
1 Citation for Chaetocin
Citations are publications that use Tocris products. Selected citations for Chaetocin include:
Bjoern et al (2021) Topoisomerase I inhibition and peripheral nerve injury induce DNA breaks and ATF3-associated axon regeneration in sensory neurons. Cell Rep 36 109666 PMID: 34496254
Do you know of a great paper that uses Chaetocin from Tocris? Please let us know.
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