Deoxyviolacein
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| Category | Others |
| Catalog number | BBF-04224 |
| CAS | 5839-61-2 |
| Molecular Weight | 327.34 |
| Molecular Formula | C20H13N3O2 |
| Purity | >99% by HPLC |
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Description
It is a minor, more hydrophobic co-metabolite of violacein, a useful bacterial pigment.
Specification
| Synonyms | (3E)-3-[1,2-Dihydro-5-(1H-indol-3-yl)-2-oxo-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one2H-Indol-2-one; 3-[(4E)-2-(1H-Indole-3-yl)-5-oxo-2-pyrroline-4-ylidene]indoline-2-one |
| Storage | Store at -20°C |
| IUPAC Name | 3-[2-hydroxy-5-(1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one |
| Canonical SMILES | C1=CC=C2C(=C1)C(=CN2)C3=CC(=C(N3)O)C4=C5C=CC=CC5=NC4=O |
| InChI | 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/h1-10,21,23-24H |
| InChI Key | JHKIFAKMDLEWJK-UHFFFAOYSA-N |
| Source | Chromobacterium violaceum |
Properties
| Appearance | Violet Blue Solid |
| Boiling Point | 755.2±60.0°C (Predicted) |
| Melting Point | >300°C |
| Density | 1.466±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Antiplasmodial and trypanocidal activity of violacein and deoxyviolacein produced from synthetic operons
Elizabeth Bilsland, Stephen G Oliver, Tatyana A Tavella, James Ajioka, Renata Krogh, Jamie E Stokes, Annabelle Roberts, David R Spring, Adriano D Andricopulo, Fabio T M Costa BMC Biotechnol . 2018 Apr 11;18(1):22. doi: 10.1186/s12896-018-0428-z.
Background:Violacein is a deep violet compound that is produced by a number of bacterial species. It is synthesized from tryptophan by a pathway that involves the sequential action of 5 different enzymes (encoded by genes vioA to vioE). Violacein has antibacterial, antiparasitic, and antiviral activities, and also has the potential of inducing apoptosis in certain cancer cells.Results:Here, we describe the construction of a series of plasmids harboring the complete or partial violacein biosynthesis operon and their use to enable production of violacein and deoxyviolacein in E.coli. We performed in vitro assays to determine the biological activity of these compounds against Plasmodium, Trypanosoma, and mammalian cells. We found that, while deoxyviolacein has a lower activity against parasites than violacein, its toxicity to mammalian cells is insignificant compared to that of violacein.Conclusions:We constructed E. coli strains capable of producing biologically active violacein and related compounds, and propose that deoxyviolacein might be a useful starting compound for the development of antiparasite drugs.
2. Bioprocess for co-production of polyhydroxybutyrate and violacein using Himalayan bacterium Iodobacter sp. PCH194
Vijay Kumar, Sanjay Kumar, Sanyukta Darnal, Subhash Kumar, Dharam Singh Bioresour Technol . 2021 Jan;319:124235. doi: 10.1016/j.biortech.2020.124235.
The co-production of industrially relevant biopolymers/biomolecules from microbes is of biotechnological importance. Herein, a unique bacterium, Iodobacter sp. PCH 194 from the kettle lake at Sach Pass in western Indian Himalaya was identified. It co-produces biopolymer polyhydroxyalkanoates (PHA) and biomolecule (violacein pigment). Statistical optimization yielded dual products in the medium augmented with glucose (4.0% w/v) and tryptone (0.5% w/v) as carbon and nitrogen sources, respectively. The purified PHA was polyhydroxybutyrate (PHB), and pigment constitutes of violacein (50-60%) and deoxyviolacein (40-50%). A bench-scale bioprocess in 22.0 L fermentor with 20% dissolved O2supply produced PHB (11.0 ± 1.0 g/L, 58% of dry cell mass) and violacein pigment (1.5 ± 0.08 g/L). PHB obtained was used for the preparation of bioplastic film. Violacein pigment experimentally validated for anticancerous and antimicrobial activities. In summary, a commercially implied bioprocess developed for the co-production of PHB and violacein pigment using the Himalayan bacterium.
3. Metabolic engineering of the violacein biosynthetic pathway toward a low-cost, minimal-equipment lead biosensor
Nai-Xing Zhang, De-Long Zhu, Juan Yi, Chang-Ye Hui, Yan Guo, Li-Mei Li Biosens Bioelectron . 2022 Oct 15;214:114531. doi: 10.1016/j.bios.2022.114531.
Metabolic engineered bacteria have been successfully employed to produce various natural colorants, which are expected to be used as the visually recognizable signals to develop mini-equipment biological devices for monitoring toxic heavy metals. The violacein biosynthetic pathway has been reconstructed in Escherichia coli (E. coli). Here the successful production of four violacein derivatives was achieved by integrating metabolic engineering and synthetic biology. Lead binding to the metalloregulator enables whole-cell colorimetric biosensors capable of assessing bioavailable lead. Deoxyviolacein-derived signal showed the most satisfied biosensing properties among prodeoxyviolacein (green), proviolacein (blue), deoxyviolacein (purple), and violacein (navy). The limit of detection (LOD) of pigment-based biosensors was 2.93 nM Pb(II), which is lower than that of graphite furnace atomic absorption spectrometry. Importantly, a good linear dose-response model in a wide dose range (2.93-6000 nM) was obtained in a non-cytotoxic deoxyviolacein-based biosensor, which was significantly better than cytotoxic violacein-based biosensor (2.93-750 nM). Among ten metal ions, only Cd(II) and Hg(II) exerted a slight influence on the response of the deoxyviolacein-based biosensor toward Pb(II). The deoxyviolacein-based biosensor was validated in detecting bioaccessible Pb(II) in environmental samples. Factors such as low cost and minimal-equipment requirement make this biosensor a suitable biological device for monitoring toxic lead in the environment.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
