4α-Phorbol 12-myristate 13-acetate | 16561-29-8

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4α-Phorbol 12-myristate 13-acetate
• 英文别名: phorbol 13-acetate 12-myristate
• CAS: 16561-29-8；63597-44-4；123409-55-2
• 化学式: C₃₆H₅₆O₈
• 分子量: 616.836
• InChiKey: PHEDXBVPIONUQT-LNHLYFGJSA-N

物化性质

• 熔点：
  65-79oC
• 沸点：
  571.87°C (rough estimate)
• 密度：
  1.17±0.1 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  可溶于DMSO，DMSO 溶液可以在20℃下避光保存至少六个月。

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  44.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  130.36
• 氢给体数：
  3.0
• 氢受体数：
  8.0

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  Xi
• 安全说明：
  S36/37
• 危险类别码：
  R38
• WGK Germany：
  3
• 海关编码：
  29153900
• 危险品运输编号：
  2928
• 危险类别：
  6.1(a)
• RTECS号：
  QH4377000
• 包装等级：
  II
• 危险性防范说明：
  P201,P202,P260,P262,P264,P270,P271,P280,P284,P301+P310+P330,P302+P352+P310,P304+P340+P310,P305+P351+P338+P310,P308+P313,P332+P313,P361+P364,P403+P233,P405,P501
• 危险性描述：
  H300+H310+H330,H315,H318,H351

制备方法与用途

佛波酯

佛波酯又称佛波醇酯、大戟二萜醇酯，是巴豆油中的成分，十四烷酸和佛波醇形成的酯。已证实是一种促癌剂。其促癌活性大小不一，活性最高的是12-邻十四烷酰大戟二萜醇-13-乙酸酯(TPA)，其余依次为大戟二萜醇-12，13-双癸酸酯、大戟二萜醇-12，13-双丁酸酯、4-邻甲基大戟二萜酸-12-十四烷酰-13-乙酸酯、大戟二萜醇-12，13-双癸酸酯。促癌机制不很清楚，近期认为与启动细胞膜相互作用，促进第二信使的合成和增加蛋白激酶活性有关。 佛波酯能激活导致细胞增殖或分化的信号通路而具有促进细胞癌变的作用。其中活性最高的是12-邻-14-烷酰佛波醇-13-乙酸酯。

生物活性

Phorbol 12-myristate 13-acetate (PMA, 12-O-Tetradecanoylphorbol-13-acetate, TPA)是一种有效的PKC激活剂，在纳摩尔浓度范围内具有活性作用。Phorbol 12-myristate 13-acetate (PMA)可诱导sphingosine-1-phosphate (S1P)。

靶点

PKC 11.7 nM (EC 50 )

体外研究

In order to examine the role of PKC in p38MAPK phosphorylation, the cells are stimulated with the PKC activator, PMA (100 nM), which mimics the binding of DAG, the natural activator of PKC, to the C1 region of the PKCs. p38MAPK phosphorylation by PMA is observed in the two cell types similar to that observed by GnRH in αT3-1 cells, that is, a slow sustained activation (3.2-fold and 3.6-fold, respectively at 30 min). The paradoxical findings that PKCs activated by GnRH and PMA play a differential role in p38MAPK phosphorylation may be explained by differential localization of the PKCs. Basal, GnRH- and PMA- stimulation of p38MAPK phosphorylation in αT3-1 cells is mediated by Ca ²⁺ influx via voltage-gated Ca ²⁺ channels and Ca ²⁺ mobilization, while in the differentiated LβT2 gonadotrope cells it is mediated only by Ca ²⁺ mobilization.
THP-1 cells are differentiated into macrophage-like cells (THP-1 macrophages) by incubation in the presence of PMA (200 ng/mL; 1-5 days), which leads to a macrophage-like phenotype characterized by changes in morphology and increased cell surface expression of CD11 and CD14.
In the monocytic cell line THP-1, PMA results in a more differentiated phenotype than VD3, according to adherence, loss of proliferation, phagocytosis of latex beads, and expression of CD11b and CD14.

体内研究

PMA is a PKC agonist, which reverses the damage induced by 5-hydroxydecanoic acid (5-HD). Thus, activation of the mitoKATP protected mitochondrial function in SOD and MDA via the PKC pathway.

类别

有毒物品

毒性分级

剧毒

急性毒性

静脉- 小鼠 LD50: 0.309 毫克/公斤

可燃性危险特性

可燃, 火场排出辛辣刺激烟雾

储运特性

库房通风低温干燥; 与食品分开储运

灭火剂

水, 砂土, 泡沫