Violacein

Violacein is a bacterial metabolite originally isolated from C. violaceum that has antibacterial and antiprotozoal activities. It is produced by C. violaceum as a purple pigment in response to N-hexanoyl homoserine lactone (Cay-10007896), a property that has been modified to create a strain of C. violaceum used in detecting quorum-sensing molecules. 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). 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.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: 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.