Virstatin | CAS#88909-96-0 | V. cholerae inhibitor

MedKoo Cat#: 145476 | Name: Virstatin

Description:

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

Virstatin, a small molecule, has been reported to inhibit virulence regulation in V. cholerae. VIRSTATIN has been described to impair the virulence of Vibrio cholerae by preventing the expression of its virulence factor, the toxin coregulated pilus (type IV pilus). Virstatin is a small molecule that inhibits virulence regulation in Vibrio cholerae, thereby preventing intestinal colonization in an infant mouse model for cholera.

Chemical Structure

Virstatin

CAS#88909-96-0

Theoretical Analysis

MedKoo Cat#: 145476

Name: Virstatin

CAS#: 88909-96-0

Chemical Formula: C16H13NO4

Exact Mass: 283.0800

Molecular Weight: 283.28

Elemental Analysis: C, 67.84; H, 4.63; N, 4.94; O, 22.59

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Virstatin; Isodibut;

IUPAC/Chemical Name

4-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)butanoic acid

InChi Key

ZHXRDXTYPCPBTI-UHFFFAOYSA-N

InChi Code

1S/C16H13NO4/c18-13(19)8-3-9-17-15(20)11-6-1-4-10-5-2-7-12(14(10)11)16(17)21/h1-2,4-7H,3,8-9H2,(H,18,19)

SMILES Code

OC(=O)CCCN1C(=O)C2=CC=CC3=C2C(=CC=C3)C1=O

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 283.28 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.

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

1: Jana SK, Gucchait A, Paul S, Saha T, Acharya S, Hoque KM, Misra AK, Chatterjee BK, Chatterjee T, Chakrabarti P. Virstatin-Conjugated Gold Nanoparticle with Enhanced Antimicrobial Activity against the Vibrio cholerae El Tor Biotype. ACS Appl Bio Mater. 2021 Apr 19;4(4):3089-3100. doi: 10.1021/acsabm.0c01483. Epub 2021 Mar 23. PMID: 35014397. 2: Nait Chabane Y, Mlouka MB, Alexandre S, Nicol M, Marti S, Pestel-Caron M, Vila J, Jouenne T, Dé E. Virstatin inhibits biofilm formation and motility of Acinetobacter baumannii. BMC Microbiol. 2014 Mar 12;14:62. doi: 10.1186/1471-2180-14-62. PMID: 24621315; PMCID: PMC4007623. 3: Shakhnovich EA, Hung DT, Pierson E, Lee K, Mekalanos JJ. Virstatin inhibits dimerization of the transcriptional activator ToxT. Proc Natl Acad Sci U S A. 2007 Feb 13;104(7):2372-7. doi: 10.1073/pnas.0611643104. Epub 2007 Feb 5. PMID: 17283330; PMCID: PMC1892951. 4: Shakhnovich EA, Sturtevant D, Mekalanos JJ. Molecular mechanisms of virstatin resistance by non-O1/non-O139 strains of Vibrio cholerae. Mol Microbiol. 2007 Dec;66(6):1331-41. doi: 10.1111/j.1365-2958.2007.05984.x. Epub 2007 Nov 6. PMID: 17986190. 5: Chatterjee T, Pal A, Dey S, Chatterjee BK, Chakrabarti P. Interaction of virstatin with human serum albumin: spectroscopic analysis and molecular modeling. PLoS One. 2012;7(5):e37468. doi: 10.1371/journal.pone.0037468. Epub 2012 May 23. PMID: 22649528; PMCID: PMC3359307. 6: Wang H, Silva AJ, Benitez JA. 3-Amino 1,8-naphthalimide, a structural analog of the anti-cholera drug virstatin inhibits chemically-biased swimming and swarming motility in vibrios. Microbes Infect. 2017 Jun;19(6):370-375. doi: 10.1016/j.micinf.2017.03.003. Epub 2017 Apr 6. PMID: 28392408; PMCID: PMC5457706. 7: Oh MH, Choi CH. Role of LuxIR Homologue AnoIR in Acinetobacter nosocomialis and the Effect of Virstatin on the Expression of anoR Gene. J Microbiol Biotechnol. 2015 Aug;25(8):1390-400. doi: 10.4014/jmb.1504.04069. PMID: 25975610. 8: Reffuveille F, Nicol M, Dé E, Thébault P. Design of an anti-adhesive surface by a pilicide strategy. Colloids Surf B Biointerfaces. 2016 Oct 1;146:895-901. doi: 10.1016/j.colsurfb.2016.07.037. Epub 2016 Jul 20. PMID: 27469573. 9: Chatterjee T, Mukherjee D, Dey S, Pal A, Hoque KM, Chakrabarti P. Accessory cholera enterotoxin, Ace, from Vibrio cholerae: structure, unfolding, and virstatin binding. Biochemistry. 2011 Apr 12;50(14):2962-72. doi: 10.1021/bi101673x. Epub 2011 Mar 18. PMID: 21366345. 10: Cushnie TP, Cushnie B, Lamb AJ. Alkaloids: an overview of their antibacterial, antibiotic-enhancing and antivirulence activities. Int J Antimicrob Agents. 2014 Nov;44(5):377-86. doi: 10.1016/j.ijantimicag.2014.06.001. Epub 2014 Jul 15. PMID: 25130096. 11: Hung DT, Shakhnovich EA, Pierson E, Mekalanos JJ. Small-molecule inhibitor of Vibrio cholerae virulence and intestinal colonization. Science. 2005 Oct 28;310(5748):670-4. doi: 10.1126/science.1116739. Epub 2005 Oct 13. PMID: 16223984. 12: Plecha SC, Withey JH. Mechanism for inhibition of Vibrio cholerae ToxT activity by the unsaturated fatty acid components of bile. J Bacteriol. 2015 May;197(10):1716-25. doi: 10.1128/JB.02409-14. Epub 2015 Mar 2. PMID: 25733618; PMCID: PMC4402388. 13: Anthouard R, DiRita VJ. Chemical biology applied to the study of bacterial pathogens. Infect Immun. 2015 Feb;83(2):456-69. doi: 10.1128/IAI.02021-14. Epub 2014 Nov 17. PMID: 25404026; PMCID: PMC4294262. 14: Nicol M, Alexandre S, Luizet JB, Skogman M, Jouenne T, Salcedo SP, Dé E. Unsaturated Fatty Acids Affect Quorum Sensing Communication System and Inhibit Motility and Biofilm Formation of Acinetobacter baumannii. Int J Mol Sci. 2018 Jan 10;19(1):214. doi: 10.3390/ijms19010214. PMID: 29320462; PMCID: PMC5796163. 15: Childers BM, Cao X, Weber GG, Demeler B, Hart PJ, Klose KE. N-terminal residues of the Vibrio cholerae virulence regulatory protein ToxT involved in dimerization and modulation by fatty acids. J Biol Chem. 2011 Aug 12;286(32):28644-55. doi: 10.1074/jbc.M111.258780. Epub 2011 Jun 14. PMID: 21673111; PMCID: PMC3151105. 16: Satitsri S, Pongkorpsakol P, Srimanote P, Chatsudthipong V, Muanprasat C. Pathophysiological mechanisms of diarrhea caused by the Vibrio cholerae O1 El Tor variant: an in vivo study in mice. Virulence. 2016 Oct 2;7(7):789-805. doi: 10.1080/21505594.2016.1192743. Epub 2016 May 24. PMID: 27222028; PMCID: PMC5029298. 17: Hsiao A, Xu X, Kan B, Kulkarni RV, Zhu J. Direct regulation by the Vibrio cholerae regulator ToxT to modulate colonization and anticolonization pilus expression. Infect Immun. 2009 Apr;77(4):1383-8. doi: 10.1128/IAI.01156-08. Epub 2009 Jan 21. PMID: 19168737; PMCID: PMC2663140. 18: Waldor MK. Disarming pathogens--a new approach for antibiotic development. N Engl J Med. 2006 Jan 19;354(3):296-7. doi: 10.1056/NEJMcibr054591. PMID: 16421373.