20350-15-6

• 常用中文名：布雷菲德菌素A
• 常用英文名：Brefeldin A
• CAS号：20350-15-6
• 分子式：C₁₆H₂₄O₄
• 分子量：280.359
• 相关类别： 原料药 抗生素类药物 其它抗生素类药
• 发布时间：2018-06-29 19:24:05
• 更新时间：2024-01-02 13:50:04
• Brefeldin A 是一种真菌代谢物，为选择性的 autophagy 抑制剂，同时可增强 CRISPR/Cas9 的活性。

名称

• 中文名: 布雷非德菌素 A
• 英文名: brefeldin A
• 中文别名: BFA/布雷非德菌素A; 布雷菲尔得菌素A; 布雷非德菌素A; 布雷菲德菌素A,蓝菌素 A; 布雷菲德菌素A
• 英文别名: 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

物化性质

• 密度: 1.1±0.1 g/cm3
• 沸点: 492.7±45.0 °C at 760 mmHg
• 熔点: 200-205ºC
• 分子式: C₁₆H₂₄O₄
• 分子量: 280.359
• 闪点: 180.8±22.2 °C
• 精确质量: 280.167450
• PSA: 66.76000
• LogP: 1.61
• 外观性状: 白色固体
• 蒸汽压: 0.0±2.8 mmHg at 25°C
• 折射率: 1.513
• 储存条件:

  2-8℃

• 稳定性: 常温常压下稳定，避免接触强氧化物
• 分子结构:

  五、分子性质数据：

  1、 摩尔折射率：76.06

  2、 摩尔体积(m³/mol)：252.9

  3、 等张比容(90.2K)：636.4

  4、 表面张力(dyne/cm)：40.0

  5、 极化率(10-24cm³)：30.15

• 计算化学:

  1、疏水参数计算参考值（XlogP）:2

  2、氢键供体数量：2

  3、氢键受体数量：4

  4、可旋转化学键数量:0

  5、互变异构体数量：

  6、拓扑分子极性表面积（TPSA）:66.8

  7、重原子数量：20

  8、表面电荷：0

  9、复杂度：388

  10、同位素原子数量：0

  11、确定原子立构中心数量：5

  12、不确定原子立构中心数量：0

  13、确定化学键立构中心数量：2

  14、不确定化学键立构中心数量：0

  15、共价键单元数量：1

• 更多:

  1.性状：未确定

  2.密度（g/mL,25/4℃）：未确定

  3.相对蒸汽密度（g/mL,空气=1）：未确定

  4.熔点（ºC）：200-205

  5.沸点（ºC,常压）：未确定

  6.沸点（ºC,5.2kPa）：未确定

  7.折射率：未确定

  8.闪点（ºC）：87

  9.比旋光度（º）：未确定

  10.自燃点或引燃温度（ºC）：未确定

  11.蒸气压（kPa,25ºC）：未确定

  12.饱和蒸气压（kPa,60ºC）：未确定

  13.燃烧热（KJ/mol）：未确定

  14.临界温度（ºC）：未确定

  15.临界压力（KPa）：未确定

  16.油水（辛醇/水）分配系数的对数值：未确定

  17.爆炸上限（%,V/V）：未确定

  18.爆炸下限（%,V/V）：未确定

  19.溶解性：未确定

生物活性

• 描述: Brefeldin A是蛋白质运输 (protein trafficking) 的特异性抑制剂,其阻断蛋白质从内质网向高尔基复合体的转运。
• 相关类别:
  信号通路 >> 自噬 >> 自噬
  信号通路 >> 细胞周期/DNA损伤 >> CRISPR/Cas9
  信号通路 >> 自噬 >> 自噬
  天然产物 >> 其他
  研究领域 >> 癌症
• 靶点:

  CRISPR/Cas9

• 体外研究: 布雷菲德菌素A治疗15小时或40小时,引起内质网(ER)的显着肿胀并将其定位转移至正常大鼠肾(NRK)细胞的外周。延长的布雷菲德菌素A治疗导致MT和肌动蛋白细胞骨架的显着破坏[1]。 BARS的ADP-核糖基化通过在布雷菲德菌素A和ADPR之间形成缀合物来介导。当与来自BFA处理的CD38 + HeLa细胞的培养基一起孵育时,BARS显示BAC结合[2]。 Brefeldin A在MDA-MB-231乳腺癌细胞中诱导不依赖贴壁的细胞死亡,抑制3D和2D培养物中MDA-MB-231集落的形成,并抑制MDA-MB的迁移和MMP 9(Matrix Metallopeptidase 9)活性-231 [3]。
• 细胞实验: 将细胞在玻璃盖玻片上生长，在PBS中的3％多聚甲醛中固定（在室温下10分钟），然后在PBS中洗涤。在室温下用PBS中的0.01％Triton X-100透化细胞7分钟。将盖玻片洗涤（在PBS / 0.2％吐温中3次），在PBS / O.4％鱼皮明胶/0.2%吐温（5分钟）和PBS / 2.5％山羊血清/0.2%吐温（5分钟）中孵育。 。封闭后，将细胞与一抗在37℃温育45分钟，然后用PBS / 0.2％吐温洗涤（5次，每次5分钟）。在37℃下加入第二抗体30分钟，然后如上洗涤细胞。将盖玻片以9：1甘油/ PBS与0.1％邻苯二胺的载玻片安装在载玻片上。
• 参考文献:

  [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.

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

毒性和生态

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

安全

• 符号: GHS06
• 信号词: Danger
• 危害声明: H301
• 警示性声明: P301 + P310
• 个人防护装备: Eyeshields;Faceshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)
• 危害码 (欧洲): Xn: Harmful;T: Toxic;
• 风险声明 (欧洲): R25
• 安全声明 (欧洲): 24/25-45-36-26
• 危险品运输编码: UN 2811 6
• WGK德国: 3
• RTECS号: GY8410000
• 危险类别: 6.1
• 海关编码: 29411090

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