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
CAS Number	88899-55-2^N
ChemSpider	10251049^Y
DrugBank	DB06733^Y
ECHA InfoCard	100.150.187
PubChem CID	6436223
Properties
Chemical formula	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).
N verify (what is ^YN ?)
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

↑ Bafilomycin A1 product page from Fermentek
↑ 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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