Deoxyviolacein
(Synonyms: 紫色杆菌素) 目录号 : GC40654A bacterial metabolite with anticancer properties
Cas No.:5839-61-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Deoxyviolacein is a bacterial metabolite and byproduct in the biosynthesis of the bisindole alkaloid violacein that has anticancer, antibacterial, and antifungal properties. It inhibits proliferation of hepatocellular carcinoma cells when used at concentrations ranging from 0.1 to 1 µM. Deoxyviolacein (125 µg/ml) has antibacterial activity against Gram-positive bacteria, including S. aureus, B. subtilis, and B. megaterium. It also has antifungal activity against R. solani when used at a concentration of 2 mg/ml.
| Cas No. | 5839-61-2 | SDF | |
| 别名 | 紫色杆菌素 | ||
| Canonical SMILES | O=C(N1)/C(C2=C1C=CC=C2)=C3C(NC(C4=CNC5=C4C=CC=C5)=C/3)=O | ||
| 分子式 | C20H13N3O2 | 分子量 | 327.3 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0553 mL | 15.2765 mL | 30.553 mL |
| 5 mM | 0.6111 mL | 3.0553 mL | 6.1106 mL |
| 10 mM | 0.3055 mL | 1.5277 mL | 3.0553 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Pathway redesign for Deoxyviolacein biosynthesis in Citrobacter freundii and characterization of this pigment
Appl Microbiol Biotechnol 2012 Jun;94(6):1521-32.PMID:22391969DOI:10.1007/s00253-012-3960-0.
Violacein (Vio) is an important purple pigment with many potential bioactivities. Deoxyviolacein, a structural analog of Vio, is always synthesized in low concentrations with Vio in wild-type bacteria. Due to Deoxyviolacein's low production and difficulties in isolation and purification, little has been learned regarding its function and potential applications. This study was the first effort in developing a stable and efficient biosynthetic system for producing pure Deoxyviolacein. A recombinant plasmid with vioabce genes was constructed by splicing using an overlapping extension-polymerase chain reaction, based on the Vio-synthesizing gene cluster of vioabcde, originating from Duganella sp. B2, and was introduced into Citrobacter freundii. With the viod gene disrupted in the Vio synthetic pathway, Vio production was completely abolished and the recombinant C. freundii synthesized only Deoxyviolacein. Interestingly, vioe gene expression was strongly stimulated in the viod-deleted recombinant strain, indicating that viod disruptions could potentially induce polar effects upon the downstream vioe gene within this small operon. Deoxyviolacein production by this strain reached 1.9 g/L in shaker flasks. The product exhibited significant acid/alkali and UV resistance as well as significant inhibition of hepatocellular carcinoma cell proliferation at low concentrations of 0.1-1 μM. These physical characteristics and antitumor activities of Deoxyviolacein contribute to illuminating its potential applications.
Antiplasmodial and trypanocidal activity of violacein and Deoxyviolacein produced from synthetic operons
BMC Biotechnol 2018 Apr 11;18(1):22.PMID:29642881DOI: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.
Microbial production of the drugs violacein and Deoxyviolacein: analytical development and strain comparison
Biotechnol Lett 2012 Apr;34(4):717-20.PMID:22187076DOI:10.1007/s10529-011-0827-x.
Violacein and Deoxyviolacein display a broad range of interesting biological properties but their production is rarely distinguished due to the lack of suitable analytical methods. An HPLC method has been developed for the separation and quantification of violacein and Deoxyviolacein and can determine the content of both molecules in microbial cultures. A comparison of different production microorganisms, including recombinant Escherichia coli and the natural producer Janthinobacterium lividum, revealed that the formation of violacein and Deoxyviolacein is strain-specific but showed significant variation during growth although the ratio between the two compounds remained constant.
Intermediate-sensor assisted push-pull strategy and its application in heterologous Deoxyviolacein production in Escherichia coli
Metab Eng 2016 Jan;33:41-51.PMID:26506462DOI:10.1016/j.ymben.2015.10.006.
Because high-throughput screening tools are typically unavailable when using the pathway-engineering approach, we developed a new strategy, named intermediate sensor-assisted push-pull strategy, which enables sequential pathway optimization by incorporating a biosensor targeting a key pathway intermediate. As proof of concept, we constructed an L-Trp biosensor and used it to optimize the Deoxyviolacein biosynthetic pathway, which we divided into two modules with L-Trp being the product of the upstream and the substrate of the downstream module for Deoxyviolacein synthesis. Using the biosensor and fluorescence-activated cell sorting, the activities of the two modules were sequentially and independently optimized in Escherichia coli to achieve the desired phenotypes. By this means, we increased the Deoxyviolacein titer 4.4-fold (1.92 g/L), which represents the greatest Deoxyviolacein production reported. This work suggests that a biosynthetic pathway can be enhanced to produce a value-added secondary metabolite(s) without available end-product screening method by using a central metabolic junction molecule biosensor(s).
Systems metabolic engineering of Escherichia coli for gram scale production of the antitumor drug Deoxyviolacein from glycerol
Biotechnol Bioeng 2014 Nov;111(11):2280-9.PMID:24889673DOI:10.1002/bit.25297.
Deoxyviolacein is a microbial drug with biological activity against tumors, gram-positive bacteria, and fungal plant pathogens. Here, we describe an Escherichia coli strain for heterologous production of this high-value drug from glycerol. Plasmid-based expression of the Deoxyviolacein cluster vioABCE was controlled by the araBAD promoter and induction by L-arabinose. Through elimination of L-arabinose catabolism in E. coli, the pentose sugar could be fully directed to induction of Deoxyviolacein biosynthesis and was no longer metabolized, as verified by (13) C isotope experiments. Deletion of the araBAD genes beneficially complemented with previously described (i) engineering of the pentose phosphate pathway, (ii) chorismate biosynthesis, (iii) tryptophan biosynthesis, (iv) improved supply of L-serine, (v) elimination of tryptophan repression, and (vi) of tryptophan catabolism. Subsequent screening of the created next-generation producer E. coli dVio-8 identified glycerol as optimum carbon source and a level of 100 mg L(-1) of L-arabinose as optimum for induction. Transferred to a glycerol-based fed-batch process, E. coli dVio-8 surpassed the gram scale and produced 1.6 g L(-1) Deoxyviolacein. With straightforward extraction from culture broth and purification by flash chromatography, Deoxyviolacein was obtained at >99.5% purity. Biotechnol. Bioeng. 2014;111: 2280-2289. © 2014 Wiley Periodicals, Inc.