Chemistry:Virstatin

From HandWiki
Short description: Molecule that inhibits the activity of a cholera protein
Virstatin
Virstatin.jpg
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC16H13NO4
Molar mass283.283 g·mol−1
3D model (JSmol)
Density1.40 g/cm3
Melting point180–183 °C (356–361 °F)
Boiling point536.52 °C (997.74 °F)

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 a simple two-step synthesis[4]

References

  1. 1.0 1.1 "Chemical biology applied to the study of bacterial pathogens". Infection and Immunity 83 (2): 456–69. February 2015. doi:10.1128/IAI.02021-14. PMID 25404026. 
  2. "Small-molecule inhibitor of Vibrio cholerae virulence and intestinal colonization". Science 310 (5748): 670–4. October 2005. doi:10.1126/science.1116739. PMID 16223984. Bibcode2005Sci...310..670H. 
  3. "Alkaloids: an overview of their antibacterial, antibiotic-enhancing and antivirulence activities". International Journal of Antimicrobial Agents 44 (5): 377–86. November 2014. doi:10.1016/j.ijantimicag.2014.06.001. PMID 25130096. https://zenodo.org/record/1004771. 
  4. "A Two-Step Synthesis of Virstatin, A Virulence Inhibitor of Vibrio cholerae". J. Chem. Educ. 86 (4): 482. 2009. doi:10.1021/ed086p482. Bibcode2009JChEd..86..482M.