A bacterial metabolite with diverse biological activities
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Bafilomycin B1

Item No. 14005

Technical Information
Formal Name
4-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-4-oxo-2E-butenoic acid, (2R,4R,5S,6R)-tetrahydro-2-hydroxy-2-[(1S,2R,3S)-2-hydroxy-3-[(2R,3S,4E,6E,9S,10S,11R,12E,14Z)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxooxacyclohexadeca-4,6,12,14-tetraen-2-yl]-1-methylbutyl]-5-methyl-6-(1-methylethyl)-2H-pyran-4-yl ester
CAS Number
88899-56-3
Synonyms
  • Setamycin
Molecular Formula
C44H65NO13
Formula Weight
Purity
≥97%
A crystalline solid
DMSO: SolubleMethanol: Unstable
SMILES
C[C@H]([C@@](C[C@H]1OC(/C=C/C(NC(C(CC2)=O)=C2O)=O)=O)(O[C@H](C(C)C)[C@H]1C)O)[C@H](O)[C@@H]([C@](OC(/C(OC)=C/C(C)=C/[C@@H](C)[C@@H](O)[C@@H](C)C3)=O)([H])[C@H](/C=C/C=C3\C)OC)C
InChi Code
InChI=1S/C44H65NO13/c1-23(2)41-28(7)35(56-37(49)18-17-36(48)45-38-31(46)15-16-32(38)47)22-44(53,58-41)30(9)40(51)29(8)42-33(54-10)14-12-13-24(3)19-26(5)39(50)27(6)20-25(4)21-34(55-11)43(52)57-42/h12-14,17-18,20-21,23,26-30,33,35,39-42,46,50-51,53H,15
InChi Key
KFUFLYSBMNNJTF-ANDWMEETSA-N
Origin
Bacterium/Streptomyces hygroscopicus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Bafilomycin B1 is a bacterial metabolite that has been found in Streptomyces and has diverse biological activities.1,2,3,4,5,6 It inhibits the activity of rat liver lysosomal vacuolar H+-ATPase (V-ATPase) in a concentration-dependent manner.4 Bafilomycin B1 (10-1,000 nM) induces autophagosome accumulation in MCF-7 cells.5 It inhibits chloroquine-induced apoptosis in primary cerebellar granule neurons (CGNs) when used at a concentration of 1 nM.3 Bafilomycin B1 reduces viral genome copy numbers in the culture supernatant of Vero E6 cells infected with H1N1 influenza A.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bowman, E.J., Siebers, A., and Altendorf, K. Bafilomycins: A class of inhibitors of membrane ATPases from microorganisms, animal cells, and plant cells. Proc. Natl. Acad. Sci. USA 85(21), 7972-7976 (1988).

    2. Yamamoto, A., Tagawa, Y., Yoshimori, T., et alBafilomycin A1 prevents maturation of autophagic vacuoles by inhibiting fusion between autophagosomes and lysosomes in rat hepatoma cell line, H-4-II-E cells. Cell Struct. Funct. 23(1), 33-42 (1998).

    3. Shacka, J.J., Klocke, B.J., and Roth, K.A. Autophagy, bafilomycin and cell death: The "A-B-Cs" of plecomacrolide-induced neuroprotection. Autophagy 2(3), 228-230 (2006).

    4. Papini, E., de Bernard, M., Bugnoli, M., et alCell vacuolization induced by Helicobacter pylori: Inhibition by bafilomycins A1, B1, C1 and D. FEMS Microbiol. Lett. 113(2), 155-159 (1993).

    5. Carr, G., Williams, D.E., Díaz-Marrero, A.R., et alBafilomycins produced in culture by Streptomyces spp. isolated from marine habitats are potent inhibitors of autophagy. J. Nat. Prod. 73(3), 422-427 (2010).

    6. Xie, X., Lu, S., Pan, X., et alAntiviral bafilomycins from a feces-inhabiting Streptomyces sp. J. Nat. Prod. 84(2), 537-543 (2021).