Bafilomycin A1

Names

[ Name ]:
Bafilomycin A1

[Synonym ]:
(5R)-2,4-Dideoxy-1-C-{(2S,3R,4S)-3-hydroxy-4-[(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]pentan-2-yl}-5-isopropyl-4-methyl-α-D-threo-pentopyranose
α-D-threo-Pentopyranose, 2,4-dideoxy-1-C-[(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]-4-methyl-5-C-(1-methylethyl)-, (5R)-
21-O-de(3-carboxy-1-oxo-2-propenyl)-2-demethyl-2-methoxy-24-methyl-hygrolidin
bafilomycin A
MFCD06795130
Oxacyclohexadeca-3,5,11,13-tetraen-2-one, 8-hydroxy-16-[(1S,2R,3S)-2-hydroxy-1-methyl-3-[(2R,4R,5S,6R)-tetrahydro-2,4-dihydroxy-5-methyl-6-(1-methylethyl)-2H-pyran-2-yl]butyl]-3,15-dimethoxy-5,7,9,11-
α-D-threo-Pentopyranose, 2,4-dideoxy-1-C-[(1S,2R,3S)-2-hydroxy-3-[(3S,4Z,6Z,9S,10S,11R,12Z,14E)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxooxacyclohexadeca-4,6,12,14-tetraen-2-yl]-1-met hylbutyl]-4-methyl-5-C-(1-methylethyl)-, (5R)-
(5R)-2,4-Dideoxy-1-C-{(2S,3R,4S)-3-hydroxy-4-[(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]-2-pentanyl}-5-isopropyl-4- ;methyl-α-D-threo-pentopyranose
BafilomycinA1fromStreptomycesgriseus
(5R)-2,4-Dideoxy-1-C-{(2S,3R,4S)-3-hydroxy-4-[(3S,4Z,6Z,9S,10S,11R,12Z,14E)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxooxacyclohexadeca-4,6,12,14-tetraen-2-yl]-2-pentanyl}-5-isopropyl-4-met ;hyl-α-D-threo-pentopyranose
BAFILOMYCIN A1
bafilomycin
tetramethyl-, (3Z,5E,7R,8S,9S,11E,13E,15S,16R)-
(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-8-Hydroxy-16-[(1S,2R,3S)-2-hydroxy-1-Methyl-3-[(2R,4R,5S,6R)-tetrahydro-2,4-dihydroxy-5-Methyl-6-(1-Methylethyl)-2H-pyran-2-yl]butyl]-3,15-diMethoxy-5,7,9,11-tetraMethyloxacyclohexadeca-3,5,11,13-tetraen-2-o
(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-8-Hydroxy-16-((1S,2R,3S)-2-hydroxy-1-methyl-3-((2R,4R,5S,6R)-tetrahydro-2,4-dihydroxy-5
Bafilomycin A1 from Streptomycesgriseus,10 ug
α-D-threo-Pentopyranose, 2,4-dideoxy-1-C-[(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]-4-methyl-5-C-(1-methylethyl)-, (5R)-

Biological Activity

[Description]:

Bafilomycin A1, a macrolide antibiotic isolated from the Streptomyces species, is a specific inhibitor of vacuolar-type H+ ATPase.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Proton Pump

Research Areas >> Cancer

Research Areas >> Infection

[Target]

H+ ATPase[1]

[In Vitro]

Bafilomycin A1 at a low concentration (1 nM) effectively and specifically inhibits and kills pediatric B-cell acute lymphoblastic leukemia cells. It targets both early and late stages of the autophagy pathway, mitochondria and induces caspase-independent apoptosis. Bafilomycin A1 induces the binding of Beclin 1 to Bcl-2, which further inhibits autophagy and promotes apoptotic cell death[1]. The growth of the BEL-7402 hepatocellular carcinoma and HO-8910 ovarian cancer cell lines are retarded and the metastatic potential is inhibited by bafilomycin A1. Transmission electron microscopy and assays of capsase-3 and −9 suggest that bafilomycin A1 induces apoptosis[2]. Bafilomycin A1 inhibits the growth of a variety of cultured cells dose-dependently, including golden hamster embryo and NIH-3T3 fibroblasts, whether or not they are transformed, and PC12 and HeLa cells. The IC50 of bafilomycin A1 for inhibition of cell growth ranges from 10 to 50 nM[3].

[In Vivo]

Chronic treatment with low-dose bafilomycin A1 (0.1 mg/kg) slightly inhibits the tumor volume, but the final tumor volume does not differ significantly from the control. However, chronic treatment with high dose bafilomycin A1 (1 mg/kg) inhibits the tumor growth significantly, compared with controls, after 21 days[4].

[Cell Assay]

Cells are harvested using 0.05% trypsin and suspended in culture medium containing 10% FCS, and 200 µL suspension is added to each well of a 96-well plate. Cells are cultured for 20 h for adhesion. Bafilomycin A1 is added to the wells at the final concentrations of 200, 400 and 800 nM, in triplicate. At 24, 48 and 72 h, 20 µl WST-1 is added to the cells. Following incubation at 37°C for 4 h, the plates are read to determine the optical density (OD) at 435 nm with 675 nm reference using a spectrophotometer[2].

[Animal admin]

Mice: Tumor-bearing mice are divided randomly into three experimental groups: a low-dose bafilomycin A1(0.1 mg/kg per day)-treated group (n=5), a high-dosebafilomycin A1(1 mg/kg per day)-treated group (n=5),and a control group (n=5). Tumor size is measured and tumor volume doubling time is calculated[2].

[References]

[1]. Yuan N, et al. Bafilomycin A1 targets both autophagy and apoptosis pathways in pediatric B-cell acute lymphoblastic leukemia. Haematologica. 2015 Mar;100(3):345-56.

[2]. Lu X, et al. Bafilomycin A1 inhibits the growth and metastatic potential of the BEL-7402 liver cancer and HO-8910 ovarian cancer cell lines and induces alterations in their microRNA expression. Exp Ther Med. 2015 Nov;10(5):1829-1834.

[3]. Ohkuma S, et al. Inhibition of cell growth by bafilomycin A1, a selective inhibitor of vacuolar H(+)-ATPase. In Vitro Cell Dev Biol Anim. 1993 Nov;29A(11):862-6.

[4]. Ohta T, et al. Bafilomycin A1 induces apoptosis in the human pancreatic cancer cell line Capan-1. J Pathol. 1998 Jul;185(3):324-30.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
770.1±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₅H₅₈O₉

[ Molecular Weight ]:
622.830

[ Flash Point ]:
232.2±26.4 °C

[ Exact Mass ]:
622.408081

[ PSA ]:
134.91000

[ LogP ]:
3.88

[ Vapour Pressure ]:
0.0±6.0 mmHg at 25°C

[ Index of Refraction ]:
1.535

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
UN 3172

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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Related Compounds

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