Virstatin

Last updated
Virstatin
Virstatin.svg
Identifiers
  • 4-(N-(1,8-naphthalimide))-n-butyric acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H13NO4
Molar mass 283.283 g·mol−1
3D model (JSmol)
Density 1.40 g/cm3
Melting point 180–183 °C (356–361 °F)
Boiling point 536.52 °C (997.74 °F)
  • c1cc2cccc3c2c(c1)C(=O)N(C3=O)CCCC(=O)O
  • 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]

The compound is an isoquinoline alkaloid [3] and can be synthesized by a simple two-step synthesis [4]

Reaction scheme used in original discovery and analysis of the molecule Virstatin reaction science.jpg
Reaction scheme used in original discovery and analysis of the molecule

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. ↑ 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. S2CID   205171789.
  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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