Inhibitor of lys9-specific HMTs
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Chaetocin

Item No. 13156

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
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
CAS Number
28097-03-2
Molecular Formula
C30H28N6O6S4
Formula Weight
696.8
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 25 mg/ml
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
InChi Code
InChI=1S/C30H28N6O6S4/c1-33-21(39)27-11-25(15-7-3-5-9-17(15)31-19(25)35(27)23(41)29(33,13-37)45-43-27)26-12-28-22(40)34(2)30(14-38,46-44-28)24(42)36(28)20(26)32-18-10-6-4-8-16(18)26/h3-10,19-20,31-32,37-38H,11-14H2,1-2H3/t19-,20-,25+,26+,27+,28+,29+,30+/m1/s1
InChi Key
PZPPOCZWRGNKIR-PNVYSBBASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Chaetocin is a fungal mycotoxin that inhibits the HMT SU(VAR)3-9 (IC50 = 0.8 μM).1 It inhibits other Lys9-specific HMTs, including G9a (IC50 = 2.5 μM) and DIM5 (IC50 = 3 μM).1 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.2,1 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).3 Chaetocin is useful both in epigenetic studies as an HMT inhibitor and in cancer research.4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Greiner, D., Bonaldi, T., Eskeland, R., et al. Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9. Nat. Chem. Biol. 1(3), 143-145 (2005).

    2. Isham, C.R., Tibodeau, J.D., Jin, W., et al. Chaetocin: A promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress. Blood 109(6), 2579-2588 (2007).

    3. Tibodeau, J.D., Benson, L.M., Isham, C.R., et al. The anticancer agent chaetocin is a competitive substrate and inhibitor of thioredoxin reductase. Antioxid. Redox Signal. 11(5), 1097-1106 (2009).

    4. Bissinger, E.M., Heinke, R., Sippl, W., et al. Targeting epigenetic modifiers: Inhibitors of histone methyltransferases. Med. Chem. Commun. 1(2), (2010).

    5. Spannhoff, A., Sippl, W., and Jung, M. Cancer treatment of the future: Inhibitors of histone methyltransferases. Int. J. Biochem. Cell Biol. 41, 4-11 (2009).

    6. Copeland, R.A., Solomon, M.E., and Richon, V.M. Protein methyltransferases as a target class for drug discovery. Nat. Rev. Drug Discov. 8, 724-732 (2009).

    Product Citations

    Coussens, N.P., Kales, S.C., Henderson, M.J., et al. High-throughput screening with nucleosome substrate identifies small-molecule inhibitors of the human histone lysine methyltransferase NSD2. The Journal of Biological Chemisty 293(35), 13750-13765 (2018).