A bacterial metabolite with anticancer properties
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Deoxyviolacein

Item No. 23477

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3E)-3-[1,2-dihydro-5-(1H-indol-3-yl)-2-oxo-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one
CAS Number
5839-61-2
Molecular Formula
C20H13N3O2
Formula Weight
327.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C(N1)/C(C2=C1C=CC=C2)=C3C(NC(C4=CNC5=C4C=CC=C5)=C/3)=O
InChi Code
InChI=1S/C20H13N3O2/c24-19-13(18-12-6-2-4-8-16(12)22-20(18)25)9-17(23-19)14-10-21-15-7-3-1-5-11(14)15/h1-10,21H,(H,22,25)(H,23,24)/b18-13+
InChi Key
OJUJNNKCVPCATE-QGOAFFKASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $296

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    2.5 mg

    $1,333

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    Cayman Chemical
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    Product Description

    Deoxyviolacein is a bacterial metabolite and byproduct in the biosynthesis of the bisindole alkaloid violacein (Item No. 27959) that has anticancer, antibacterial, and antifungal properties.1,2 It inhibits proliferation of hepatocellular carcinoma cells when used at concentrations ranging from 0.1 to 1 µM.2 Deoxyviolacein (125 µg/ml) has antibacterial activity against Gram-positive bacteria, including S. aureus, B. subtilis, and B. megaterium.1 It also has antifungal activity against R. solani when used at a concentration of 2 mg/ml.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, H., Wang, F., Zhu, X., et al. Biosynthesis and characterization of violacein, deoxyviolacein and oxyviolacein in heterologous host, and their antimicrobial activities. Biochem. Eng. J. 67, 148-155 (2012).

    2. Jiang, P.-X., Wang, H.-S., Xiao, S., et al. Pathway redesign for deoxyviolacein biosynthesis in Citrobacter freundii and characterization of this pigment. Appl. Microbiol. Biotechnol. 94(6), 1521-1532 (2012).