Violacein is an intense violet pigment formed by the condensation of two tryptophan units, found in a number of bacteria, notably Chromobacterium violaceum. The regulation of pigment biosynthesis is the chromogenic basis for the use of C. violaceum CV26 for the detection of quorum sensing mediators. Violacein cell toxicity resembles TNF-α signal transduction.</br>Violacein exhibits broad spectrum activity against bacteria, protozoans (including malaria), viruses and mammalian cell lines.
| Catalog Number | R004181 |
| CAS Number | 548-54-9 |
| Molecular Formula | C20H13N3O3 |
| Purity | 95% |
| Storage | -20°C |
| IUPAC Name | (3E)-3-[5-(5-hydroxy-1H-indol-3-yl)-2-oxo-1H-pyrrol-3-ylidene]-1H-indol-2-one |
| InChI | 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+ |
| InChIKey | XAPNKXIRQFHCHN-QGOAFFKASA-N |
| SMILES | C1=CC=C2C(=C1)C(=C3C=C(NC3=O)C4=CNC5=C4C=C(C=C5)O)C(=O)N2 |
| Reference | The chemistry of bacteria. Part II. Some degradation products of violacein. Beer R.J.S. et al. J. Chem Soc. 1949, 885.<br/><br/>Quorum sensing and Chromobacterium violaceum: exploitation of violacein production and inhibition for the detection of N-acyl homoserine lactones. McClean K.H. et al. Microbiol. 1997, 143, 3703.<br/><br/>Molecular mechanism of violacein-mediated human leukemia cell death. Ferreira C.V. et al. Blood 2004, 104, 1459.</span></p> |
