A cytotoxic alkaloid
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(–)-Chaetominine

Item No. 13135

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,4R,5aS,9cS)-4,5,5a,9c-tetrahydro-5a-hydroxy-2-methyl-4-(4-oxo-3(4H)-quinazolinyl)-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione
CAS Number
918659-56-0
Molecular Formula
C22H18N4O4
Formula Weight
402.4
Purity
≥85%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly Soluble: 0.1-1 mg/ml
SMILES
O=C1N([C@H]2C)[C@]3([H])[C@](C4=CC=CC=C4N3C2=O)(O)C[C@H]1N5C=NC(C=CC=C6)=C6C5=O
InChi Code
InChI=1S/C22H18N4O4/c1-12-18(27)26-16-9-5-3-7-14(16)22(30)10-17(20(29)25(12)21(22)26)24-11-23-15-8-4-2-6-13(15)19(24)28/h2-9,11-12,17,21,30H,10H2,1H3/t12-,17+,21-,22-/m0/s1
InChi Key
GEURDGODABUDHB-TYTLQBBQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $157

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    2.5 mg

    $703

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    Product Description

    (–)-Chaetominine is a cytotoxic alkaloid originally isolated from Chaetomium sp. IFB-E015.1 It inhibits the growth of K562 leukemia and SW1116 colon cancer cells (IC50s = 20 and 28 nM, respectively). (–)-Chaetominine induces apoptosis of K562 cells via upregulation of the Bax/Bcl-2 ratio, decreasing mitochondrial membrane potential, inducing mitochondrial cytochrome C release, and activation of caspase-3 and caspase-9.2 It also decreases doxorubicin efflux mediated by multidrug resistance-associated protein 1 (MRP1) and restores sensitivity to doxorubicin (Item No. 15007) in resistant K562 cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jiao, R.H., Xu, S., Liu, J.Y., et al. Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015. Org. Lett. 8(25), 5709-5712 (2006).

    2. Yao, J., Jiao, R.H., Liu, C., et al. Assessment of the cytotoxic and apoptotic effects of chaetominine in a human leukemia cell line. Biomol. Ther. (Seoul) 24(2), 147-155 (2016).

    3. Yao, J., Wei, X., and Lu, Y. Chaetominine reduces MRP1-mediated drug resistance via inhibiting PI3K/Akt/Nrf2 signaling pathway in K562/Adr human leukemia cells. Biochem. Biophys. Res. Commun. 473(4), 867-873 (2016).