| Identification | Back Directory | [Name]
BAFILOMYCIN B1 | [CAS]
88899-56-3 | [Synonyms]
BAFILOMYCIN B1
BAFILOMYCIN B1 USP/EP/BP
ino)carbonyl)-2-methoxy-24-methyl-
bafilomycin b1from streptomyces sp.
BafilomycinB1fromStreptomycesgriseus
BAFILOMYCIN B1 MONOHYDRATE FROM STREPTO- MYCES SPECIES
hygrolidin,37-decarboxy-2-demethyl-37-(((2-hydroxy-5-oxo-1-cyclopenten-1-yl)am
37-De(carboxy)-2-demethyl-37-[[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]carbonyl]-2-methoxy-24-methylhygrolidin
2-Butenoic acid, 4-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-4-oxo-, (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-methylethy... | [Molecular Formula]
C44H65NO13 | [MDL Number]
MFCD00242671 | [MOL File]
88899-56-3.mol | [Molecular Weight]
815.99 |
| Chemical Properties | Back Directory | [storage temp. ]
−20°C
| [solubility ]
DMSO: Soluble; Methanol: Unstable | [form ]
powder or crystals | [color ]
faint yellow to yellow | [BRN ]
4640118 | [Stability:]
Hygroscopic | [InChIKey]
KFUFLYSBMNNJTF-JUFZODOZSA-N | [SMILES]
C1(O)(C(C)C(O)C(C)C2OC(=O)C(OC)=CC(C)=CC(C(O)C(C)CC(C)=CC=CC2OC)C)OC(C(C)C(OC(=O)/C=C/C(=O)NC2=C(O)CCC2=O)C1)C(C)C |c:28,t:14,17,26| |
| Hazard Information | Back Directory | [Description]
Bafilomycin B1 is a fungal 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 | [Uses]
Bafilomycin B1 is a member of a potent family of macrocyclic lactones. Bafilomycin B1 shares the same mode of action and activity as its more accessible A1 analogue. Bafilomycin B1 is broadly active against bacteria, fungi, insects, nematodes and protozoans. Bafilomycin B1 has attracted interest as a potential agent for treating osteoporosis. | [IC 50]
Macrolide | [References]
[1] E J BOWMAN K A A Siebers. Bafilomycins: a class of inhibitors of membrane ATPases from microorganisms, animal cells, and plant cells.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1988, 85 21: 7972-7976. DOI: 10.1073/pnas.85.21.7972
[2] A YAMAMOTO. Bafilomycin A1 prevents maturation of autophagic vacuoles by inhibiting fusion between autophagosomes and lysosomes in rat hepatoma cell line, H-4-II-E cells.[J]. Cell structure and function, 1998, 23 1: 33-42. DOI: 10.1247/csf.23.33
[3] JOHN J SHACKA Kevin A R Barbara J Klocke. Autophagy, bafilomycin and cell death: the “a-B-cs” of plecomacrolide-induced neuroprotection.[J]. Autophagy, 2006, 2 3: 228-230. DOI: 10.4161/auto.2703
[4] EMANUELE PAPINI . Cell vacuolization induced by Helicobacter pylori: Inhibition by bafilomycins A1, B1, C1 and D[J]. Fems Microbiology Letters, 1993, 113 2: Pages 155-159.
[5] GAVIN CARR. Bafilomycins Produced in Culture by Streptomyces spp. Isolated from Marine Habitats Are Potent Inhibitors of Autophagy?[J]. Journal of Natural Products , 2009, 73 3: 422-427. DOI: 10.1021/np900632r
[6] XI XIE. Antiviral Bafilomycins from a Feces-Inhabiting Streptomyces sp.[J]. Journal of Natural Products , 2021, 84 2: 537-543. DOI: 10.1021/acs.jnatprod.0c01243 |
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