Bafilomycin A1

Modify Date: 2024-01-03 16:15:12

Bafilomycin A1 Structure
Bafilomycin A1 structure
 Common Name Bafilomycin A1
CAS Number 88899-55-2 Molecular Weight 622.830
Density 1.1±0.1 g/cm3 Boiling Point 770.1±60.0 °C at 760 mmHg
Molecular Formula C35H58O9 Melting Point N/A
MSDS Chinese USA Flash Point 232.2±26.4 °C

 Use of Bafilomycin A1


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

 Names

Name bafilomycin A1
Synonym More Synonyms

 Bafilomycin A1 Biological Activity

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

 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

Name: Bafilomycin A1 Material Safety Data Sheet
Synonym:
CAS: 88899-55-2
Section 1 - Chemical Product MSDS Name:Bafilomycin A1 Material Safety Data Sheet
Synonym:
Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
88899-55-2 Bafilomycin A1 unlisted
Hazard Symbols: XI
Risk Phrases: 36/37/38
Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
Not available.
Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use extinguishing media most appropriate for the surrounding fire.
Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.
Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a tightly closed container. Deep freeze (below -20C).
Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 88899-55-2: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.
Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble in ethanol
Specific Gravity/Density:
Molecular Formula:
Molecular Weight: 622.80
Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.
Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 88899-55-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Bafilomycin A1 - Not listed by ACGIH, IARC, or NTP.
Section 12 - ECOLOGICAL INFORMATION

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.
Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.
Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 88899-55-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 88899-55-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 88899-55-2 is not listed on the TSCA inventory.
It is for research and development use only.

SECTION 16 - ADDITIONAL INFORMATION
N/A

 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

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 Synonyms

(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)-
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