Bafilomycin B1
Molecular Formula
C44H65NO13
M.W.
816.00
CAS number
88899-56-3
Source
Streptomyces sp.
Fermentek product Code
BFB-001
Brand/grade
For research
Appearance
Yellow powder
Purity by HPLC
≥95% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Solubility test
Clear yellow solution at 5mg/ml Methanol ;
Clear yellow solution at 5mg/ml DMSO ;
Names and identifiers

Synonyms

  • Hygrolidin, 37-decarboxy-2-demethyl-37-[[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]carbonyl]-2-methoxy-24-methyl
  • Setamycin
  • Bafilomycin B1

IUPAC Name

  • (5R)-2,4-Dideoxy-1-C-{(2S,3R,4S)-3-hydroxy-4-[(3S,4Z,9S,10S,11R)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxooxacyclohexadeca-4,6,12,14-tetraen-2-yl]-2-pentanyl}-3-O-{(2E)-4-[(2-hydroxy-5-ox ;o-1-cyclopenten-1-yl)amino]-4-oxo-2-butenoyl}-5-isopropyl-4-methyl-α-D-threo-pentopyranose

 RTECS: NG8841000

EU number
635-481-1
Chemical name
Bafilomycin B1
Description

Bafilomycin B1 is a specific inhibitor of vacuolar type H+-ATPase (V-ATPase) in animal cells, plant cells and microorganisms.

Bafilomycin B1  can prevent the re-acidification of synaptic vesicles once they have undergone exocytosis.

It displays Antibacterial, Antifungal, Antineoplastic, Immunosuppressive properties.

Bafilomycin B1 shares the same mode of action and activity as its more accessible Bafilomycin A1 analogue. Bafilomycin B1 is broadly active against bacteria, fungi, insects, nematodes and protozoans. Bafilomycin B1 has attracted interest as a potential antiosteoporotic agent in treating bone lytic diseases.

Bafilomycins have been considered as possible therapeutic agents in the treatment of gastritis.

InChl Key
KFUFLYSBMNNJTF-MZYUNMTESA-N
Canonical SMILES
CC1CC(=CC=CC(C(OC(=O)C(=CC(=CC(C1O)C)C)OC)C(C)C(C(C)C2(CC(C(C(O2)C(C)C)C)OC(=O)C=CC(=O)NC3=C(CCC3=O)O)O)O)OC)C
Isomeric SMILES
C[C@H]1C/C(=C\C=C/[C@@H](C(OC(=O)/C(=C\C(=C/[C@H]([C@H]1O)C)\C)/OC)[C@@H](C)[C@H]([C@H](C)[C@]2(C[C@H]([C@@H]([C@H](O2)C(C)C)C)OC(=O)/C=C/C(=O)NC3=C(CCC3=O)O)O)O)OC)/C
Solubility ( literature )

Reportedly soluble in ethanol, methanol, DMF or DMSO. Attention: may form methyl ketal on long term storage in methanol

Compound Classification

Macrolide antibiotic

Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Protect from light !
Use the original container to store the product.
Keep the lid tightly closed.
Store under argon.
shipped at ambient temperature. Stored under inert atmosphere.
Applications

Bafilomycins specificly  inhibit  vacuolar type H+-ATPase (V-ATPase) in animal cells, plant cells and microorganisms. Bafilomycin A1 is useful in distinguishing among different types of ATPases. Bafilomycin A1 can prevent the re-acidification of synaptic vesicles once they have undergone exocytosis. Bafilomycin A1 and B1 significantly attenuate cerebellar granule neuron death resulting from agents that disrupt lysosome. As vacuolar ATPase inhibitors bafilomycins overcome Bcl-​xL-​mediated chemoresistance through restoration of a caspase-​independent apoptotic pathway.

Disclaimer
For Research use only
Not for Human or Drug use
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Ingredient type
Fermentek product
Available since
Title
Transport information
Value
II or III but basic information is not credible, no quantitative data available
Title
Deleted CAS Numbers
Value
80112-34-1; used with name Setamycin only
Signal to sort
B