Virstatin

Virstatin
Identifiers
IUPAC name
  • 4-(N-(1,8-naphthalimide))-n-butyric acid
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H13NO4
Molar mass283.283 g·mol−1
3D model (JSmol)
Density1.40 g/cm3
Melting point86–88 °C (187–190 °F)
Boiling point536.52 °C (997.74 °F)
SMILES
  • c1cc2cccc3c2c(c1)C(=O)N(C3=O)CCCC(=O)O
InChI
  • InChI=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)
  • Key:ZHXRDXTYPCPBTI-UHFFFAOYSA-N

Virstatin is a small molecule that inhibits the activity of the cholera protein, ToxT.[1]

Its activity in cholera was first published in 2005 in a paper that described the screening of a chemical library in a phenotypic screen and subsequent testing of one of the hits in infected mice.[1][2]

Reaction scheme used in original discovery and analysis of the molecule

The compound is an isoquinoline alkaloid[3] and can be synthesized by reacting 1,8-naphthalic anhydride with 4-amino-n-butyric acid[2] or by a simple two-step synthesis[4]

References

  1. 1 2 Anthouard R, DiRita VJ (February 2015). "Chemical biology applied to the study of bacterial pathogens". Infection and Immunity. 83 (2): 456–69. doi:10.1128/IAI.02021-14. PMC 4294262. PMID 25404026.
  2. 1 2 Hung DT, Shakhnovich EA, Pierson E, Mekalanos JJ (October 2005). "Small-molecule inhibitor of Vibrio cholerae virulence and intestinal colonization". Science. 310 (5748): 670–4. Bibcode:2005Sci...310..670H. doi:10.1126/science.1116739. PMID 16223984. S2CID 30557147.
  3. ↑ Cushnie TP, Cushnie B, Lamb AJ (November 2014). "Alkaloids: an overview of their antibacterial, antibiotic-enhancing and antivirulence activities". International Journal of Antimicrobial Agents. 44 (5): 377–86. doi:10.1016/j.ijantimicag.2014.06.001. PMID 25130096.
  4. ↑ McDonald CE (2009). "A Two-Step Synthesis of Virstatin, A Virulence Inhibitor of Vibrio cholerae". J. Chem. Educ. 86 (4): 482. Bibcode:2009JChEd..86..482M. doi:10.1021/ed086p482.
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