cyctochalasin B | 14930-96-2

• 物质功能分类: 原料药 - 抗生素类药物 - 其它抗生素类药
• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 细胞松弛素类
• 英文名称: cyctochalasin B
• 英文别名: cytochalasin B；7β,20β-dihydroxy-16α-methyl-10-phenyl-24-oxa-[14]cytochalasa-6(12),13t,21t-triene-1,23-dione；7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione；Phomin；cytochalasin-B；19-Benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
• CAS: 14930-96-2
• 化学式: C₂₉H₃₇NO₅
• 分子量: 479.616
• InChiKey: GBOGMAARMMDZGR-UHFFFAOYSA-N

物化性质

• 熔点：
  218-223 °C
• 沸点：
  577.96°C (rough estimate)
• 密度：
  1.1490 (rough estimate)
• 闪点：
  85℃
• 溶解度：
  乙醇：20 mg/mL
• LogP：
  3.370
• 颜色/状态：
  FELTED NEEDLES FROM ACETONE
• 旋光度：
  SPECIFIC OPTICAL ROTATION: +86.7 DEG @ 21 °C/D (C= 0.9 IN METHANOL), +84 DEG @ 25 °C/D (C= 1.0 IN ETHANOL); MP: 218 °C, FROM CHLOROFORM SOLUTION; MAX ABSORPTION: 229 NM (E= 44,668), 257 NM (SHOULDER), 265 NM (SHOULDER), 269 NM (SHOULDER)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

ADMET

代谢

在Phoma属真菌合成细胞松弛素B（Phomin）和Zygosporium masonii合成细胞松弛素D的生物合成过程中，向Phoma属真菌提供了若干（14）C和（3）H前体，并进行了精确的降解反应，以揭示细胞松弛素B的形成，它由一个单位的苯丙氨酸、九个单位的醋酸-丙二酸单位和两个单位的甲硫氨酸组成。在细胞松弛素D的情况下，也确认了这种标记模式。

...IN THE BIOSYNTHESES OF CYTOCHALASIN B (PHOMIN) BY PHOMA SPECIES & CYTOCHALASIN D BY ZYGOSPORIUM MASONII...A NUMBER OF (14)C & (3)H PRECURSORS WERE FED TO PHOMA SPECIES & PRECISE DEGRADATION REACTIONS WERE PERFORMED TO REVEAL THE FORMATION OF CYTOCHALASIN B FROM ONE UNIT OF PHENYLALANINE, NINE UNITS OF ACETATE-MALONATE, & TWO UNITS OF METHIONINE. THE LABELLING PATTERN WAS ALSO CONFIRMED IN THE CASE OF CYTOCHALASIN D.

来源:Hazardous Substances Data Bank (HSDB)

代谢

由拟茎点霉（Phoma species）通过酶催化的拜耳-维利格型氧插入直接转化标记的去氧柄菌素证明了柄菌素B（Phomin）的形成。

THE FORMATION OF CYTOCHALASIN B (PHOMIN) BY AN ENZYMATIC BAYER-VILLIGER TYPE OXYGEN INSERTION WAS PROVED BY A DIRECT CONVERSION OF LABELLED DEOXAPHOMIN BY PHOMA SPECIES.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

使用微丝解聚剂细胞松弛素B处理野生型S49淋巴瘤细胞，可逆地并以剂量高度依赖性方式增强随后添加β-肾上腺素能激动剂（-）异丙肾上腺素、前列腺素E1或霍乱毒素时细胞内环磷酸腺苷的积累。

TREATMENT OF WILD TYPE S49 LYMPHOMA CELLS WITH THE MICROFILAMENT DISRUPTER CYTOCHALASIN B REVERSIBLY & IN A HIGHLY DOSE-DEPENDENT FASHION ENHANCES CELLULAR CYCLIC AMP ACCUMULATION IN RESPONSE TO SUBSEQUENT ADDITION OF THE BETA-ADRENERGIC AGONIST (-)-ISOPROTERENOL, PROSTAGLANDIN E1, OR CHOLERA TOXIN.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

细胞松弛素B无法转化3T3样肿瘤细胞，但确实增加了由多瘤病毒引起的细胞转化的频率，增加了8-40倍。

CYTOCHALASIN B WAS UNABLE TO TRANSFORM 3T3-LIKE TUMOR CELLS, BUT DID INCREASE 8-40 FOLD THE FREQUENCY OF CELL TRANSFORMATION BY POLYOMA VIRUS.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

聚球菌素A诱导的变形虫原虫素活动，通过细胞松弛素B大大增强。

THE PINOCYTOTIC ACTIVITY, INDUCED BY CONCANAVALIN A IN AMOEBA PROTEUS, IS GREATLY INTENSIFIED BY CYTOCHALASIN B.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

细胞松弛素 B 抑制了小麦叶鞘段在吲哚-3-乙酸作用下的伸长和玉米根的伸长，唯一发生的超微结构变化是分泌囊泡的积累。细胞松弛素 B 明显通过抑制囊泡运输和细胞壁组分的分泌来阻断伸长生长。

CYTOCHALASIN B INHIBITED THE ELONGATION OF WHEAT COLEOPTILE SEGMENTS IN INDOLE-3-ACETIC ACID & OF MAIZE ROOTS, WITH THE ONLY ULTRASTRUCTURAL CHANGES BEING THE ACCUMULATION OF SECRETORY VESICLES. CYTOCHALASIN B APPARENTLY BLOCKED ELONGATION GROWTH BY INHIBITING VESICLE TRANSPORT & SECRETION OF CELL WALL COMPONENTS.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

细胞毒素B对Hela细胞的细胞毒性：样品在DMSO中溶解，浓度为10毫克/毫升，并在培养基中稀释。盖玻片上的细胞进行了3天的处理。通过观察染色的盖玻片，估计细胞毒性的程度，范围从'0'（少量细胞损伤）到'4'（完全细胞溶解）。'2'表示大约50%的生长抑制剂量。记录了相应细胞毒性评分的特定剂量：32微克/毫升= 4评分；10微克/毫升= 3.5评分；3.2微克/毫升= 2.5评分；1.0微克/毫升= 1评分；0.32微克/毫升= 0评分。/来自表格/

CYTOTOXICITY OF CYTOCHALASIN B ON HELA CELLS: SAMPLES WERE DISSOLVED IN DMSO AT 10 MG/ML & DILUTED IN THE MEDIUM. CELLS ON COVER-GLASSES WERE TREATED FOR 3-DAYS. DEGREE OF CYTOTOXICITY WAS ESTIMATED ON A SCALE RANGING '0' (LITTLE CELLULAR DAMAGE) THROUGH '4' (COMPLETE CYTOLYSIS) IN OBSERVING THE STAINED COVER-GLASSES. '2' DENOTES APPROXIMATE 50% GROWTH-INHIBITORY DOSE. SPECIFIC DOSAGE WITH RESPECTIVE CYTOTOXICITY RATING WAS NOTED: 32 UG/ML= 4 RATING; 10 UG/ML= 3.5 RATING; 3.2 UG/ML= 2.5 RATING; 1.0 UG/ML= 1 RATING; 0.32 UG/ML= 0 RATING. /FROM TABLE/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  T+
• 安全说明：
  S28,S36/37,S45
• 危险类别码：
  R26/27/28,R63
• WGK Germany：
  2,3
• 海关编码：
  29349990
• 危险品运输编号：
  UN 1544 6
• RTECS号：
  RO0205000
• 包装等级：
  I
• 危险类别：
  6.1(a)
• 储存条件：
  -20°C

SDS

Name:	Cytochalasin B 98% (TLC) Material Safety Data Sheet
Synonym:	None Known
CAS:	14930-96-2

Section 1 - Chemical Product MSDS Name:Cytochalasin B 98% (TLC) Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14930-96-2	Cytochalasin B	98%	239-000-2

Hazard Symbols: T+
Risk Phrases: 26/27/28 40

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Very toxic by inhalation, in contact with skin and if swallowed.
Limited evidence of a carcinogenic effect.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. May cause cardiac disturbances. May cause central nervous system depression.
Inhalation:
May cause respiratory tract irritation. May cause cardiac abnormalities. Inhalation at high concentrations may cause CNS depression and asphixiation.
Chronic:
Effects may be delayed. Adverse reproductive effects have been reported in animals. Laboratory experiments have resulted in mutagenic effects.

---

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. Containers may explode when heated. Non-combustible, substance itself does not burn but may decompose upon heating to produce irritating, corrosive and/or toxic fumes. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray to cool fire-exposed containers. For small fires, use dry chemical, carbon dioxide, or water spray. For large fires, use dry chemical, carbon dioxide, alcohol-resistant foam, or water spray.

---

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. 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. Poison room locked/refrigerator.

---

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# 14930-96-2: 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 minimize contact with skin.
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
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 221.00 - 223.00 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: insoluble
Specific Gravity/Density:
Molecular Formula: C29H37NO5
Molecular Weight: 479.60

---

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:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 14930-96-2: RO0205000 LD50/LC50:
Not available.
Carcinogenicity:
Cytochalasin B - 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
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: II

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T+
Risk Phrases:
R 26/27/28 Very toxic by inhalation, in contact with
skin and if swallowed.
R 40 Limited evidence of a carcinogenic effect.
Safety Phrases:
S 1 Keep locked up.
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# 14930-96-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14930-96-2 is listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14930-96-2 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

细胞松弛素B在细胞内与微丝的正端结合，导致F-肌动蛋白解聚，并阻止亚基进一步聚合。当将其加入活细胞后，肌动蛋白纤维骨架消失，使动物细胞的各种活动瘫痪，包括细胞移动、吞噬作用和胞质分裂等。

生物活性

Cytochalasin B 是一种能透过细胞的真菌毒素，能够与肌动蛋白丝的有刺端结合，扰乱肌动蛋白聚合物的形成。其对F-actin的Kd值为1.4-2.2 nM。

靶点

Cytochalasin B 的Kd值分别为：

• F-actin (含Mg²⁺) 2.2 nM
• F-actin (含Mg²⁺/K⁺) 1.4 nM

体外研究

Cytochalasin B 是一种细胞渗透性霉菌毒素，能够结合肌动蛋白丝的有刺端，抑制肌动蛋白纤维的伸长和缩短。其对F-actin (含2 mM MgCl₂) 的Kd值为2.2 nM，在存在2 mM MgCl₂ 和KCl的情况下分别为1.4 nM。

Cytochalasin B 在0.1-10 μM 浓度范围内对多种小鼠癌细胞系表现出抑制作用，3小时后的半数有效浓度 (IC₅₀) 分别为：

• M109c 2.56 μM
• B16BL6 10.46 μM
• P388/ADR 105.5 μM
• P388/S 51.9 μM

在4天后的半数有效浓度 (IC₈₀) 分别为：

• M109c 12.23 μM
• B16BL6 44.86 μM
• P388/ADR 188.4 μM
• P388/S 84.1 μM

此外，Cytochalasin B 可以增加肌纤维碎片指数 (MFI)，并加速肌动蛋白纤维的分解。在死后处理期间，它还能促进F-actin向G-actin的转化，降低F-actin含量，并显著提高G-actin带。

体内研究

Cytochalasin B 在10, 25, 50 mg/kg (腹腔注射) 的剂量下能显著增加Balb/c小鼠携带P388/ADR白血病的生存期。在P388/ADR多药抗性组中，50 mg/kg 的剂量可产生10%长期存活率，在药物敏感P388/S组中则为40%。

用途

细胞松弛素B是首个用于研究细胞骨架的药物，它由真菌分泌，是一种生物碱。当加入活细胞后，其与微丝正端结合引起F-肌动蛋白解聚并阻止亚基进一步聚合。这会导致肌动蛋白纤维骨架消失，使动物细胞的各种活动瘫痪，包括细胞移动、吞噬作用和胞质分裂等。它对微管没有影响，也不抑制肌肉收缩，因为肌纤维中的肌动蛋白丝是稳定的结构，不会发生组装及解聚的动态平衡。