Polyene antimycotic

Polyene antimycotics, sometimes referred to as polyene antibiotics, are a class of antimicrobial polyene compounds that target fungi.[1] These polyene antimycotics are typically obtained from some species of Streptomyces bacteria. The polyenes bind to ergosterol in the fungal cell membrane and promote leakiness which may contribute to fungal cell death. Amphotericin B, nystatin, and natamycin are examples of polyene antimycotics.

Contents

Structures

Their chemical structures feature a large ring of atoms (essentially a cyclic ester ring) containing multiple conjugated carbon-carbon double bonds (hence polyene) on one side of the ring and multiple hydroxyl groups bonded to the other side of the ring. Their structures also often have a d-mycosamine (a type of amino-glycoside) group bonded to the molecule.[2] The series of conjugated double bonds typically absorbs strongly in the ultraviolet-visible region of the electromagnetic spectrum, often resulting in the polyene antibiotics having a yellow color.

Biosynthesis

The natural route to synthesis includes polyketide synthase components.[3]

Other examples of polyenes

References

  1. ^ NCBI Bookshelf (1996). "Polyene Antifungal Drugs". The University of Texas Medical Branch at Galveston. http://www.ncbi.nlm.nih.gov/bookshelf/br.fcgi?book=mmed&part=A4050. Retrieved 29 January 2010. 
  2. ^ Solution NMR structure of five representative glycosylated polyene macrolide antibiotics
  3. ^ Khan N, Rawlings B, Caffrey P (2011 Jan 26). "A labile point in mutant amphotericin polyketide synthases". Biotechnol Lett.. PMID 21267757.