A competitive NQO1 inhibitor
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Dicoumarol

Item No. 20764

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,3'-methylenebis[4-hydroxy-2H-1-benzopyran-2-one
CAS Number
66-76-2
Synonyms
  • NSC 17860
  • NSC 41834
  • NSC 221570
Molecular Formula
C19H12O6
Formula Weight
336.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1.25 mg/mlDMSO: 2.5 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: Slight solubility
λmax
309 nm
SMILES
O=C1C(CC2=C(O)C(C=CC=C3)=C3OC2=O)=C(O)C4=CC=CC=C4O1
InChi Code
InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
InChi Key
DOBMPNYZJYQDGZ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Dicoumarol is a competitive inhibitor of NADH:quinone oxidoreductase (NQO1) with IC50 values of 2.6 and 404 nM in the absence and presence of 2 μM BSA, respectively.1 It has antiproliferative activity against MIA PaCa-2 pancreas and HCT116 colon carcinoma cells (IC50s = 52 and 19 μM, respectively, after a 96 hour incubation). Dicoumarol inhibits stress-activated protein kinase (SAPK) in HEK293 cells (IC50 = 19-33 μM) at a point upstream of MEKK1 and downstream of TNF receptor-associated factor 2 (TRAF2), and it inhibits TNF-α and LPS-induced NF-κB activation in HeLa cells.2 It also has antiproliferative activity against FL5.12 lymphocytic and MCF-7 breast carcinoma cells (100 μM) by suppressing JNK activation.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nolan, K.A., Doncaster, J.R., Dunstan, M.S., et al. Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: Quinone oxidoreductase-1 (NQO1). J. Med. Chem. 52(22), 7142-7156 (2009).

    2. Cross, J.V., Deak, J.C., Rich, E.A., et al. Quinone reductase inhibitors block SAPK/JNK and NFκB pathways and potentiate apoptosis. The Journal of Biological Chemisty 274(44), 31150-31154 (1999).

    3. Krause, D., Lyons, A., Fennelly, C., et al. Transient activation of Jun N-terminal kinases and protection from apoptosis by the insulin-like growth factor I receptor can be suppressed by dicumarol. The Journal of Biological Chemisty 276(22), 19244-19252 (2001).