Virstatin

Virstatin
Identifiers
	IUPAC name 4-(N-(1,8-naphthalimide))-n-butyric acid;
CAS Number	88909-96-0 ;
PubChem CID	145949;
ChemSpider	128749;
ChEMBL	ChEMBL403272;
CompTox Dashboard (EPA)	DTXSID10237406 ;
Chemical and physical data
Formula	C16H13NO4
Molar mass	283.283 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.40 g/cm3
Melting point	180–183 °C (356–361 °F)
Boiling point	536.52 °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]

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

References

^ ^a ^b 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.
^ 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.
^ 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.
^ 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.

[Anthouard2015rev-1] 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.

[Hung2005-2] 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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