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16561-29-8

中文名稱 佛波醇12-十四酸酯13-乙酸酯
英文名稱 PHORBOL 12-MYRISTATE 13-ACETATE
CAS 16561-29-8
分子式 C36H56O8
MDL 編號 MFCD00036736
分子量 616.83
MOL 文件 16561-29-8.mol
更新日期 2024/12/25 17:21:35
16561-29-8 結構式 16561-29-8 結構式

基本信息

中文別名
佛波醇12-十四酸酯13-乙酸酯
豆蔻酰佛波醇乙酯
乙酸佛波酯 PMA
乙酸佛波酯
英文別名
12-O-TETRADECANOYLPHORBOL 13-ACETATE
12-TETRADECANOYL PHORBOL 13-ACETATE
(1AR,1BS,4AR,7AS,7BS,8R,9R,9AS)-9A-(ACETYLOXY)-1A,1B,4,4A,5,7A,7B,8,9,9A-DECAHYDRO-4A,7B-DIHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-5-OXO-1H-CYCLOPROPA[3,4]BENZ[1,2-E]AZULEN-9-YL TETRADECANOATE
4ALPHA,9ALPHA,12BETA,13ALPHA,20-PENTAHYDROXYTIGLIA-1,6-DIEN-3-ONE 12BETA-MYRISTATE 13-ACETATE
4BETA,9ALPHA,12BETA,13ALPHA,20-PENTA-HYDROXYTIGLIA-1,6-DIEN-3-ONE 12BETA-MYRISTATE 13-ACETATE
4BETA-PHORBOL 12-MYRISTATE 13-ACETATE
PHORBOL 12-MYRISTATE 13-ACETATE
PHORBOL (12-MYRISTOYL-13-ACETYL)
PMA
TPA
,9aalpha))-
1,6,8-beta-tetramethyl-l)-9a-acetate9-myristate
12-o-tetradecanoylphorbolacetate
12-o-tetradekanoylphorbol-13-acetat
12-tetradecanoylphorbol13-monoacetate
13-o-acetylphorbol12-myristate
4)benz(1,2-e)azulen-5-one9a-acetate,(+)-ethyl-5h-cyclopropa(
5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one,1,1a-beta,1b-alpha,4,4a,7a-beta,7b,
8,9,9a-decahydro-4a-alpha,7b-beta,9-alpha,9a-beta-tetrahydroxy-3-(hydroxymethy
abeta,7balpha,9beta,9aalpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetram
所屬類別
化學試劑:酸酯類化合物

物理化學性質

熔點65-79oC
沸點571.87°C (rough estimate)
密度1.17±0.1 g/cm3 (20 ºC 760 Torr)
折射率1.4900 (estimate)
儲存條件−20°C
儲存條件-20°C
溶解度DMSO: DMSO solutions can be stored dark at −20?#x00b0;C for at least six months.soluble
溶解度可溶于DMSO,DMSO 溶液可以在20℃下避光保存至少六個月。
酸度系數(shù)(pKa)11.19±0.70(Predicted)
形態(tài)精細結晶粉末
顏色灰白色至淡黃色
水溶解性Very soluble in methanol, soluble in DMSO, chloroform, ethanol or acetone, ether, ethyl acetate, DMF or acetonitrile. Insoluble in water.
敏感性感光
BRN2407201
穩(wěn)定性可在-20°下的DMSO或乙醇溶液保存長達2個月。
InChIKeyPHEDXBVPIONUQT-RGYGYFBISA-N
CAS 數(shù)據(jù)庫16561-29-8(CAS DataBase Reference)

安全數(shù)據(jù)

危險性符號(GHS)GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS05,GHS06,GHS08
警示詞危險
危險品標志Xi
危險類別碼38-36/37/38
危險類別碼R38
安全說明36/37-26
安全說明S36/37
危險品運輸編號2928
WGK Germany3
WGK Germany3
RTECS號QH4377000
危險等級6.1(a)
包裝類別II
海關編碼29153900
毒害物質數(shù)據(jù)16561-29-8(Hazardous Substances Data)
毒性Diesters of phorbol, particularly 12-O-tetradecanoylphorbol 13-acetate, also known as phorbol myristate acetate, have been identified as the potent, highly lipophilic tumor-promoting components in croton oil. They are potent promoters of skin tumors in vivo and have been shown to transform cultured fibroblasts and embryonic cells previously exposed to polycyclic aromatic hydrocarbon carcinogens in vitro. The structure of phorbol, the parent alcohol is shown below. Phorbol esters also have important effects on leukocytes and on the immune system of the intact animal. There appears to be a specific receptor for phorbol esters on T cells, a finding that may account for the selective toxicity of phorbol esters for T cells. The mechanism of tumor promotion by phorbol esters is still largely unknown, but findings suggest an initial cell membrane interaction (often with stimulation of second messenger synthesis and increased protein kinase activity), with subsequent effects on nuclear regulatory events.

16561-29-8(安全特性,毒性,儲運)

儲運特性
庫房通風低溫干燥; 與食品分開儲運
毒性分級
劇毒
急性毒性
靜脈- 小鼠 LD50: 0.309 毫克/公斤
可燃性危險特性
可燃, 火場排出辛辣刺激煙霧
類別
有毒物品
滅火劑
水, 砂土, 泡沫

常見問題列表

佛波酯
佛波酯又稱佛波醇酯、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。已證實是一種促癌劑。其促癌活性大小不一,活性最高的是12-鄰十四烷酰大戟二萜醇-13-乙酸酯(TPA),其余依次為大戟二萜醇-12,13-雙癸酸酯、大戟二萜醇-12,13-雙丁酸酯、4-鄰甲基大戟二萜酸-12-十四烷酰-13-乙酸酯、大戟二萜醇-12,13-雙癸酸酯。促癌機制不很清楚,近期認為與啟動細胞膜相互作用,促進第二信使的合成和增加蛋白激酶活性有關。 佛波酯能激活導致細胞增殖或分化的信號通路而具有促進細胞癌變的作用。其中活性最高的是12-鄰-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)是一種有效的PKC激活劑,在納摩爾濃度范圍內(nèi)具有活性作用。Phorbol 12-myristate 13-acetate (PMA)可誘導sphingosine-1-phosphate (S1P)。
靶點

PKC

11.7 nM (EC 50 )

體外研究

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.

體內(nèi)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.

佛波醇12-十四酸酯13-乙酸酯價格(試劑級)
報價日期產(chǎn)品編號產(chǎn)品名稱CAS號包裝價格
2024/11/11XW165612981佛波醇-12-十四酸酯-13-乙酸酯16561-29-85MG976元
2024/11/0835615佛波醇12-十四酸酯13-乙酸酯
Phorbol 12-myristate 13-acetate, 97%, Thermo Scientific Chemicals
16561-29-81mg1731元
2024/11/0835615佛波醇12-十四酸酯13-乙酸酯
Phorbol 12-myristate 13-acetate, 97%, Thermo Scientific Chemicals
16561-29-85mg6166元
"16561-29-8" 相關產(chǎn)品信息
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