Brefeldin A

Modify Date: 2024-01-02 13:50:04

Brefeldin A Structure
Brefeldin A structure
Common Name Brefeldin A
CAS Number 20350-15-6 Molecular Weight 280.359
Density 1.1±0.1 g/cm3 Boiling Point 492.7±45.0 °C at 760 mmHg
Molecular Formula C16H24O4 Melting Point 200-205ºC
MSDS Chinese USA Flash Point 180.8±22.2 °C
Symbol GHS06
GHS06
Signal Word Danger

 Use of Brefeldin A


Brefeldin A is a specific inhibitor of protein trafficking which blocks the protein transport from the endoplasmic reticulum to the Golgi complex.

 Names

Name brefeldin A
Synonym More Synonyms

 Brefeldin A Biological Activity

Description Brefeldin A is a specific inhibitor of protein trafficking which blocks the protein transport from the endoplasmic reticulum to the Golgi complex.
Related Catalog
Target

CRISPR/Cas9

In Vitro Brefeldin A treatment for 15 h or 40 h, causes dramatic swelling of the Endoplasmic Reticulum (ER) and shifts its localization to the periphery of normal rat kidney (NRK) cells. Prolonged Brefeldin A treatment results in marked disruption of the MT and actin cytoskeleton[1]. ADP-ribosylation of BARS is mediated by formation of a conjugate between Brefeldin A and ADPR. BARS shows BAC binding when incubated with the medium from the BFA-treated CD38+ HeLa cells[2]. Brefeldin A induces anchorage-independent cell death in MDA-MB-231 breast cancer cells, inhibits the formation of MDA-MB-231 colonies in 3D and 2D cultures and inhibits the migration and MMP 9 (Matrix Metallopeptidase 9) activity of MDA-MB-231[3].
Cell Assay Cells are grown on glass coverslips, fixed in 3 % paraformaldehyde in PBS (10 min at room temperature) and then washed in PBS. Cells are permeabilized with 0.01 % Triton X-lOO in PBS at room temperature for 7 min. The coverslips are washed (3 times in PBS/0.2 % Tween) incubated in PBS/O.4 % fish skin gelatin/0.2 % Tween (5 min) and in PBS/2.5 % goat serum/0.2 % Tween (5 min.). After blocking, the cells are incubated with primary antibodies for 45 min at 37°C, and then washed with PBS/0.2 % Tween (5 times, 5 min each). The secondary antibodies are added for 30 min at 37°C and then cells are washed as above. Coverslips are mounted on slides in 9: 1 glycerol/PBS with 0.1 % o-phenylenediamine.
References

[1]. Alvarez C, et al. Brefeldin A (BFA) disrupts the organization of the microtubule and the actin cytoskeletons. Eur J Cell Biol. 1999 Jan;78(1):1-14.

[2]. Colanzi A, et al. Molecular mechanism and functional role of brefeldin A-mediated ADP-ribosylation of CtBP1/BARS. Proc Natl Acad Sci U S A. 2013 Jun 11;110(24):9794-9.

[3]. Tseng CN, et al. Brefeldin A reduces anchorage-independent survival, cancer stem cell potential and migration of MDA-MB-231 human breast cancer cells. Molecules. 2014 Oct 29;19(11):17464-77.

[4]. Wang J, et al. Erythroleukemia cells acquire an alternative mitophagy capability. Sci Rep. 2016 Apr 19;6:24641.

[5]. Yu C, et al. Small molecules enhance CRISPR genome editing in pluripotent stem cells. Cell Stem Cell. 2015 Feb 5;16(2):142-7.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 492.7±45.0 °C at 760 mmHg
Melting Point 200-205ºC
Molecular Formula C16H24O4
Molecular Weight 280.359
Flash Point 180.8±22.2 °C
Exact Mass 280.167450
PSA 66.76000
LogP 1.61
Vapour Pressure 0.0±2.8 mmHg at 25°C
Index of Refraction 1.513
Storage condition 2~8°C

 MSDS

Name: Brefeldin A Natural Material Safety Data Sheet
Synonym:
CAS: 20350-15-6
Section 1 - Chemical Product MSDS Name:Brefeldin A Natural Material Safety Data Sheet
Synonym:

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
20350-15-6 Brefeldin A, Natural 100% unlisted
Hazard Symbols: None Listed.
Risk Phrases: None Listed.

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 20350-15-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Solid
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 203.00 - 204.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C16H24O4
Molecular Weight: 280.35

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 20350-15-6: GY8410000 LD50/LC50:
Not available.
Carcinogenicity:
Brefeldin A, Natural - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 20350-15-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 20350-15-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 20350-15-6 is not listed on the TSCA inventory.
It is for research and development use only.


SECTION 16 - ADDITIONAL INFORMATION
N/A

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GY8410000
CHEMICAL NAME :
4H-Cyclopent(f)oxacyclotridecin-4-one, 1,6,7,8,9,11a-beta,12,13,14,14a-alpha-decahydro-1- beta-13-alpha-dihydroxy-6-beta-methyl-
CAS REGISTRY NUMBER :
20350-15-6
LAST UPDATED :
199412
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C16-H24-O4
MOLECULAR WEIGHT :
280.40
WISWESSER LINE NOTATION :
T5-13- IVO GU OUTJ CQ FQ K1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - mouse Cells - not otherwise specified
DOSE/DURATION :
200 ug/L
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 39,1148,1986

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310
Personal Protective Equipment Eyeshields;Faceshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)
Hazard Codes Xn: Harmful;T: Toxic;
Risk Phrases R25
Safety Phrases 24/25-45-36-26
RIDADR UN 2811 6
WGK Germany 3
RTECS GY8410000
Hazard Class 6.1
HS Code 29411090

 Synthetic Route

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 Synonyms

4H-Cyclopent[f]oxacyclotridecin-4-one, 1,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-, (1R,2E,6S,10E,11aS,13S,14aR)-
g,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic Acid l-Lactone
Brefeldin
Synergisidin
Brefeldin A
(1R,2E,6S,10E,11aS,13S,14aR)-1,13-Dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
cyanein
1,6,7,8,9,11ab,12,13,14,14aa-Decahydro-1b,13a-dihydroxy-6b-methyl-4H-cyclopent(f)oxacyclotridecin-4-one
Cyanaein
Brefeldin-A
MFCD00083258
ASCOTOXIN
decumbin
BFA
Nectrolide
(+)-Brefeldin A
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