A bacterial metabolite with antibacterial and antiprotozoal activities
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Violacein

Item No. 27959

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3E)-3-[1,2-dihydro-5-(5-hydroxy-1H-indol-3-yl)-2-oxo-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one
CAS Number
548-54-9
Molecular Formula
C20H13N3O3
Formula Weight
343.3
Purity
≥85%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
SMILES
O=C(N1)/C(C2=C1C=CC=C2)=C3C(NC(C4=CNC5=C4C=C(O)C=C5)=C/3)=O
InChi Code
InChI=1S/C20H13N3O3/c24-10-5-6-15-12(7-10)14(9-21-15)17-8-13(19(25)23-17)18-11-3-1-2-4-16(11)22-20(18)26/h1-9,21,24H,(H,22,26)(H,23,25)/b18-13+
InChi Key
XAPNKXIRQFHCHN-QGOAFFKASA-N
Origin
Bacterium/Chromobacterium violaceum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $325

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    Product Description

    Violacein is a bacterial metabolite originally isolated from C. violaceum that has antibacterial and antiprotozoal activities.1,2 It is produced by C. violaceum as a purple pigment in response to N-hexanoyl homoserine lactone (Item No. 10007896), a property that has been modified to create a strain of C. violaceum used in detecting quorum-sensing molecules.3 Violacein is active against Gram-positive bacteria, including B. subtilis and S. aureus (MICs = 0.8 and 1.6 µM, respectively). It is also active against P. falciparum, including chloroquine-susceptible and -resistant strains (IC50s = 0.85 and 0.63 µM, respectively).2 It reduces parasitemia in a mouse model of nonlethal P. chabaudi chabaudi infection when administered at a dose of 7.5 mg/kg and increases survival in a mouse model of lethal P. chabaudi chabaudi infection. Violacein permeabilizes the cytoplasmic membrane of bacterial cells but does not affect the cell wall.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cauz, A.C.G., Carretero, G.P.B., Saraiva, G.K.V., et al. Violacein targets the cytoplasmic membrane of bacteria. ACS Infect. Dis. 5(4), 539-549 (2019).

    2. Lopes, S.C.P., Blanco, Y.C., Justo, G.Z., et al. Violacein extracted from Chromobacterium violaceum inhibits Plasmodium growth in vitro and in vivo. Antimicrob. Agents Chemother. 53(5), 2149-2152 (2009).

    3. Blosser, R.S., and Gray, K.M. Extraction of violacein from Chromobacterium violaceum provides a new quantitative bioassay for N-acyl homoserine lactone autoinducers. J. Microbiol. Methods 40(1), 47-55 (2000).