Violacein
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 584943

CAS#: 548-54-9

Description: Violacein is produced by BB-78 strain of Chromobacterium violaceum and is a bisindole antibiotic effective against Gram-positive bacteria.

Chemical Structure

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Violacein
CAS# 548-54-9
Instruction

Theoretical Analysis

MedKoo Cat#: 584943
Name: Violacein
CAS#: 548-54-9
Chemical Formula: C20H13N3O3
Exact Mass: 343.10
Molecular Weight: 343.342
Elemental Analysis: C, 69.97; H, 3.82; N, 12.24; O, 13.98

Price and Availability

Size Price Availability Quantity
1mg USD 355
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Synonym: Violacein

IUPAC/Chemical Name: 2-Indolinone, 3-(2-(5-hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene)-

InChi Key: XAPNKXIRQFHCHN-AQTBWJFISA-N

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-

SMILES Code: O=C1NC2=C(C=CC=C2)/C1=C3C=C(C4=CNC5=C4C=C(O)C=C5)NC\3=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 343.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Choi SY, Yoon KH, Lee JI, Mitchell RJ. Violacein: Properties and Production of a Versatile Bacterial Pigment. Biomed Res Int. 2015;2015:465056. doi: 10.1155/2015/465056. Epub 2015 Aug 3. Review. PubMed PMID: 26339614; PubMed Central PMCID: PMC4538413.

2: Sun H, Zhao D, Xiong B, Zhang C, Bi C. Engineering Corynebacterium glutamicum for violacein hyper production. Microb Cell Fact. 2016 Aug 24;15(1):148. doi: 10.1186/s12934-016-0545-0. PubMed PMID: 27557730; PubMed Central PMCID: PMC4997675.

3: Im H, Choi SY, Son S, Mitchell RJ. Combined Application of Bacterial Predation and Violacein to Kill Polymicrobial Pathogenic Communities. Sci Rep. 2017 Oct 31;7(1):14415. doi: 10.1038/s41598-017-14567-7. PubMed PMID: 29089523; PubMed Central PMCID: PMC5663959.

4: Ballestriero F, Daim M, Penesyan A, Nappi J, Schleheck D, Bazzicalupo P, Di Schiavi E, Egan S. Antinematode activity of Violacein and the role of the insulin/IGF-1 pathway in controlling violacein sensitivity in Caenorhabditis elegans. PLoS One. 2014 Oct 8;9(10):e109201. doi: 10.1371/journal.pone.0109201. eCollection 2014. Erratum in: PLoS One. 2018 Dec 26;13(12):e0210026. PubMed PMID: 25295516; PubMed Central PMCID: PMC4189955.

5: Dodou HV, de Morais Batista AH, Sales GWP, de Medeiros SC, Rodrigues ML, Nogueira PCN, Silveira ER, Nogueira NAP. Violacein antimicrobial activity on Staphylococcus epidermidis and synergistic effect on commercially available antibiotics. J Appl Microbiol. 2017 Oct;123(4):853-860. doi: 10.1111/jam.13547. PubMed PMID: 28744944.

6: Leal AM, de Queiroz JD, de Medeiros SR, Lima TK, Agnez-Lima LF. Violacein induces cell death by triggering mitochondrial membrane hyperpolarization in vitro. BMC Microbiol. 2015 Jun 6;15:115. doi: 10.1186/s12866-015-0452-2. PubMed PMID: 26048053; PubMed Central PMCID: PMC4457087.

7: Fang MY, Zhang C, Yang S, Cui JY, Jiang PX, Lou K, Wachi M, Xing XH. High crude violacein production from glucose by Escherichia coli engineered with interactive control of tryptophan pathway and violacein biosynthetic pathway. Microb Cell Fact. 2015 Jan 16;14:8. doi: 10.1186/s12934-015-0192-x. PubMed PMID: 25592762; PubMed Central PMCID: PMC4306242.

8: Pauer H, Hardoim CCP, Teixeira FL, Miranda KR, Barbirato DDS, de Carvalho DP, Antunes LCM, Leitão ÁADC, Lobo LA, Domingues RMCP. Impact of violacein from Chromobacterium violaceum on the mammalian gut microbiome. PLoS One. 2018 Sep 13;13(9):e0203748. doi: 10.1371/journal.pone.0203748. eCollection 2018. PubMed PMID: 30212521; PubMed Central PMCID: PMC6136722.

9: Choi SY, Kim S, Lyuck S, Kim SB, Mitchell RJ. High-level production of violacein by the newly isolated Duganella violaceinigra str. NI28 and its impact on Staphylococcus aureus. Sci Rep. 2015 Oct 22;5:15598. doi: 10.1038/srep15598. PubMed PMID: 26489441; PubMed Central PMCID: PMC4614999.

10: He L, Xiu Y, Jones JA, Baidoo EEK, Keasling JD, Tang YJ, Koffas MAG. Deciphering flux adjustments of engineered E. coli cells during fermentation with changing growth conditions. Metab Eng. 2017 Jan;39:247-256. doi: 10.1016/j.ymben.2016.12.008. Epub 2016 Dec 23. PubMed PMID: 28017690.

11: Hashimi SM, Xu T, Wei MQ. Violacein anticancer activity is enhanced under hypoxia. Oncol Rep. 2015 Apr;33(4):1731-6. doi: 10.3892/or.2015.3781. Epub 2015 Feb 4. PubMed PMID: 25652759.

12: Platt D, Amara S, Mehta T, Vercuyssee K, Myles EL, Johnson T, Tiriveedhi V. Violacein inhibits matrix metalloproteinase mediated CXCR4 expression: potential anti-tumor effect in cancer invasion and metastasis. Biochem Biophys Res Commun. 2014 Dec 5;455(1-2):107-12. PubMed PMID: 25450700; PubMed Central PMCID: PMC4293260.

13: Zhou Y, Fang MY, Li G, Zhang C, Xing XH. Enhanced Production of Crude Violacein from Glucose in Escherichia coli by Overexpression of Rate-Limiting Key Enzyme(S) Involved in Violacein Biosynthesis. Appl Biochem Biotechnol. 2018 Dec;186(4):909-916. doi: 10.1007/s12010-018-2787-2. Epub 2018 May 25. PubMed PMID: 29797295.

14: Woodhams DC, LaBumbard BC, Barnhart KL, Becker MH, Bletz MC, Escobar LA, Flechas SV, Forman ME, Iannetta AA, Joyce MD, Rabemananjara F, Gratwicke B, Vences M, Minbiole KPC. Prodigiosin, Violacein, and Volatile Organic Compounds Produced by Widespread Cutaneous Bacteria of Amphibians Can Inhibit Two Batrachochytrium Fungal Pathogens. Microb Ecol. 2018 May;75(4):1049-1062. doi: 10.1007/s00248-017-1095-7. Epub 2017 Nov 9. PubMed PMID: 29119317.

15: Devescovi G, Kojic M, Covaceuszach S, Cámara M, Williams P, Bertani I, Subramoni S, Venturi V. Negative Regulation of Violacein Biosynthesis in Chromobacterium violaceum. Front Microbiol. 2017 Mar 7;8:349. doi: 10.3389/fmicb.2017.00349. eCollection 2017. PubMed PMID: 28326068; PubMed Central PMCID: PMC5339254.

16: Immanuel SRC, Banerjee D, Rajankar MP, Raghunathan A. Integrated constraints based analysis of an engineered violacein pathway in Escherichia coli. Biosystems. 2018 Sep;171:10-19. doi: 10.1016/j.biosystems.2018.06.002. Epub 2018 Jul 3. PubMed PMID: 30008425.

17: Jiang Y, Sigmund F, Reber J, Deán-Ben XL, Glasl S, Kneipp M, Estrada H, Razansky D, Ntziachristos V, Westmeyer GG. Violacein as a genetically-controlled, enzymatically amplified and photobleaching-resistant chromophore for optoacoustic bacterial imaging. Sci Rep. 2015 Jun 19;5:11048. doi: 10.1038/srep11048. PubMed PMID: 26091543; PubMed Central PMCID: PMC4473533.

18: Mehta T, Vercruysse K, Johnson T, Ejiofor AO, Myles E, Quick QA. Violacein induces p44/42 mitogen-activated protein kinase-mediated solid tumor cell death and inhibits tumor cell migration. Mol Med Rep. 2015 Jul;12(1):1443-8. doi: 10.3892/mmr.2015.3525. Epub 2015 Mar 20. PubMed PMID: 25816226; PubMed Central PMCID: PMC4438925.

19: Kothari V, Sharma S, Padia D. Recent research advances on Chromobacterium violaceum. Asian Pac J Trop Med. 2017 Aug;10(8):744-752. doi: 10.1016/j.apjtm.2017.07.022. Epub 2017 Aug 19. Review. PubMed PMID: 28942822.

20: Aruldass CA, Masalamany SRL, Venil CK, Ahmad WA. Antibacterial mode of action of violacein from Chromobacterium violaceum UTM5 against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA). Environ Sci Pollut Res Int. 2018 Feb;25(6):5164-5180. doi: 10.1007/s11356-017-8855-2. Epub 2017 Mar 31. PubMed PMID: 28361404.