(1S,4E,6R,10R,12E,14R,15S,17S,18S,19S)-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

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (1S,4E,6R,10R,12E,14R,15S,17S,18S,19S)-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
• 化学式: C₂₉H₃₇NO₅
• 分子量: 479.6
• InChiKey: GBOGMAARMMDZGR-UWBDMDNASA-N

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菌种合成CYTOCHALASIN B (PHOMIN)和ZYGOSPORIUM MASONII合成CYTOCHALASIN D的生物合成过程中，向Phoma菌种提供了若干(14)C和(3)H前体，并进行了精确的降解反应，以揭示CYTOCHALASIN B从一单位苯丙氨酸、九单位醋酸盐-丙二酸盐和两单位蛋氨酸的形成。在CYTOCHALASIN 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

通过对标记过的去氧表霉酚通过Phoma菌种直接转化，证明了细胞松弛素B（Phomin）是通过酶催化的拜耳-维利格型氧插入反应形成的。

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

野生的S49淋巴瘤细胞用微丝解聚剂细胞松弛素B处理后，以剂量依赖性和可逆的方式增强了细胞内环磷酸腺苷（cAMP）的积累，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。

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

CYTOCHALASIN B未能转化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

康卡纳瓦酸A在变形虫中诱导的伪足活性，会被细胞松弛素B显著增强。

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生长，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

细胞松弛素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为期3天的处理。通过观察染色的盖玻片，以从'0'（细胞损伤很小）到'4'（细胞完全溶解）的等级来估计细胞毒性的程度。'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具体剂量：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)