Bafilomycin

Bafilomycin A1[1]
Names
IUPAC name
(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16- [(1S,2R,3S)-3-[(2R,4R,5S,6R)-2,4-dihydroxy-6- isopropyl-5-methyl-2-tetrahydropyranyl]-2- hydroxy-1-methylbutyl]-8-hydroxy-3,15- dimethoxy-5,7,9,11-tetramethyl-1- oxacyclohexadeca-3,5,11,13-tetraen-2-one
Identifiers
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.150.187
Properties
C35H58O9
Molar mass 622.83 g/mol
Appearance Yellow powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The bafilomycins are a family of toxic macrolide antibiotic derived from Streptomyces griseus. These compounds all appear in the same fermentation and have quite similar biological activity. Bafilomycins are specific inhibitors of vacuolar-type H+-ATPase.

The most used bafilomycin is bafilomycin A1. This is a useful tool as it can prevent the re-acidification of synaptic vesicles once they have undergone exocytosis.

Bafilomycin has antibacterial, antifungal, antineoplastic, immunosuppressive activities. In addition, bafilomycin A1 has antimalarial activity [2] It has been shown to decrease multi-drug resistance.

Bafilomycin B1 has been mentioned as a potential antiosteoporotic agent in treating bone lytic diseases.

References

  1. ↑ Bafilomycin A1 product page from Fermentek
  2. ↑ van Schalkwyk DA, Chan XW, Misiano P, Gagliardi S, Farina C, Saliba KJ. "Inhibition of Plasmodium falciparum pH regulation by small molecule indole derivatives results in rapid parasite death" Biochem Pharmacol. 2010 May 1;79(9):1291-9. PMID 20067768


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