佛波醇-12-十四烷酰-13-乙酸酯

佛波醇-12-十四烷酰-13-乙酸酯
	IUPAC名; (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(乙酰)-4a,7b-二羥基-3-(羥甲基)-1,1,6,8-四甲基-5-氧-1a,1b,4,4a,5,7a,7b,8,9,9a-十氫-H-環丙[3,4]苯並[1,2-e]薁-9-肉豆蔻酸酯
別名	TPA，PMA，佛波醇肉豆蔻酰乙酸酯，; 十四酰佛波乙酯
識別
CAS號	16561-29-8
PubChem	27924
ChemSpider	25977
SMILES	CCCCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)C)O)C;
InChI	1/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1;
InChIKey	PHEDXBVPIONUQT-RGYGYFBIBK
KEGG	C05151
性質
化學式	C36H56O8
摩爾質量	616.83 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

佛波醇-12-十四烷酰-13-乙酸酯（英語：12-O-Tetradecanoylphorbol-13-acetate，縮寫：TPA）是一種具有潛在促癌作用的佛波酯，在生物醫學研究中常用作蛋白激酶C（PKC）的激活劑。^[1]^[2]^[3] TPA對PKC的生物學活性源於它的擬甘油二酯樣作用——後者是一種經典蛋白激酶C的天然活化劑。

在自由基生物學中，不包含羥基自由基、過氧化氫、過氧亞硝酸鹽在內的超氧化物被認定系TPA而非離子黴素在小鼠巨噬細胞中產生的活性氧衍生物，因此TPA已成為誘生內源性超氧化物的常規用劑。^[4]^[5]

在細胞遺傳學試驗中，TPA被視為B細胞淋巴瘤細胞的有絲分裂原，可刺激B細胞的分裂以便於對特定細胞的染色體進行觀察，從而幫助診斷諸如慢性淋巴細胞白血病的血液癌症。^[6]

TPA與離子黴素的聯合製劑已被廣泛用於刺激T細胞的活化、增殖並產生細胞因子，亦可用作細胞內染色的助劑。^[7]

參考文獻

^ Castagna; et al. "Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters". Journal of Biological Chemistry. 1982, 257 (13): 7847–7851.
^ Blumberg. "Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture". Cancer Research. 1988, 48: 1–8.
^ Niedel; et al. Phorbol Diester Receptor Copurifies with Protein Kinase C. Proceedings of the National Academy of Sciences. 1983, 80: 36–40. doi:10.1073/pnas.80.1.36.
^ Swindle. "A Comparison of Reactive Oxygen Species Generation by Rat Peritoneal Macrophages and Mast Cells Using the Highly Sensitive Real-Time Chemiluminescent Probe Pholasin: Inhibition of Antigen-Induced Mast Cell Degranulation by Macrophage-Derived Hydrogen Peroxide". The journal of Immunology. 2002, 169: 5866–5873. .
^ Huang. "Megakaryocytic Differentiation of K562 Cells Induced by PMA Reduced the Activity of Respiratory Chain Complex IV". PLOS ONE (journal). 2014, 9: e96246. .
^ The AGT cytogenetics laboratory manual. 3rd ed. Barch, Margaret J., Knutsen, Turid., Spurbeck, Jack L., eds. 1997. Lippincott-Raven.
^ Flow Cytometry Intracellular Staining Guide. eBioscience, Inc. [2011-09-25]. （原始內容存檔於2017-01-21）.

外部連結

醫學主題詞表（MeSH）：Tetradecanoylphorbol+Acetate
NCI Dictionary Entry. [2005-07-02]. （原始內容存檔於2015-05-11）.
Phase 1 Clinical Trials. [2005-07-02]. （原始內容存檔於2020-11-06）.

[1] Castagna; et al. "Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters". Journal of Biological Chemistry. 1982, 257 (13): 7847–7851.

[2] Blumberg. "Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture". Cancer Research. 1988, 48: 1–8.

[3] Niedel; et al. Phorbol Diester Receptor Copurifies with Protein Kinase C. Proceedings of the National Academy of Sciences. 1983, 80: 36–40. doi:10.1073/pnas.80.1.36.

[4] Swindle. "A Comparison of Reactive Oxygen Species Generation by Rat Peritoneal Macrophages and Mast Cells Using the Highly Sensitive Real-Time Chemiluminescent Probe Pholasin: Inhibition of Antigen-Induced Mast Cell Degranulation by Macrophage-Derived Hydrogen Peroxide". The journal of Immunology. 2002, 169: 5866–5873. .

[5] Huang. "Megakaryocytic Differentiation of K562 Cells Induced by PMA Reduced the Activity of Respiratory Chain Complex IV". PLOS ONE (journal). 2014, 9: e96246. .

[6] The AGT cytogenetics laboratory manual. 3rd ed. Barch, Margaret J., Knutsen, Turid., Spurbeck, Jack L., eds. 1997. Lippincott-Raven.

[urlFlow_Cytometry_Intracellular_Staining_Guide-7] Flow Cytometry Intracellular Staining Guide. eBioscience, Inc. [2011-09-25]. （原始內容存檔於2017-01-21）.

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佛波醇-12-十四烷酰-13-乙酸酯

IUPAC名 (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(乙酰)-4a,7b-二羥基-3-(羥甲基)-1,1,6,8-四甲基-5-氧-1a,1b,4,4a,5,7a,7b,8,9,9a-十氫-H-環丙[3,4]苯並[1,2-e]薁-9-肉豆蔻酸酯
別名	TPA，PMA，佛波醇肉豆蔻酰乙酸酯，十四酰佛波乙酯
識別
CAS號	16561-29-8 ^Y
PubChem	27924
ChemSpider	25977
SMILES	CCCCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)C)O)C
InChI	1/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1
InChIKey	PHEDXBVPIONUQT-RGYGYFBIBK
KEGG	C05151
性質
化學式	C₃₆H₅₆O₈
摩爾質量	616.83 g·mol⁻¹
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。