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-二羟基-3-(羟甲基)-1,1,6,8-四甲基-5-氧-1a,1b,4,4a,5,7a,7b,8,9,9a-十氢-H-环丙[3,4]苯并[1,2-e]薁-9-肉豆蔻酸酯
别名	TPA，PMA，佛波醇肉豆蔻酰乙酸酯，; 十四酰佛波乙酯
识别
CAS号	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
性质
化学式	C36H56O8
摩尔质量	616.83 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

佛波醇-12-十四烷酰-13-乙酸酯（英语：12-O-Tetradecanoylphorbol-13-acetate，缩写：TPA）是一种具有潜在促癌作用的佛波酯，在生物医学研究中常用作蛋白激酶C（PKC）的激活剂。^[1]^[2]^[3] TPA对PKC的生物学活性源于它的拟甘油二酯样作用——后者是一种经典蛋白激酶C的天然活化剂。

在自由基生物学中，不包含羟基自由基、过氧化氢、过氧亚硝酸盐在内的超氧化物被认定系TPA而非离子霉素在小鼠巨噬细胞中产生的活性氧衍生物，因此TPA已成为诱生内源性超氧化物的常规用剂。^[4]^[5]

在细胞遗传学试验中，TPA被视为B细胞淋巴瘤细胞的有丝分裂原，可刺激B细胞的分裂以便于对特定细胞的染色体进行观察，从而帮助诊断诸如慢性淋巴细胞白血病的血液癌症。^[6]

TPA与离子霉素的联合制剂已被广泛用于刺激T细胞的活化、增殖并产生细胞因子，亦可用作细胞内染色的助剂。^[7]

参考文献

^ 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]. （原始内容存档于2017-01-21）.

外部链接

医学主题词表（MeSH）：Tetradecanoylphorbol+Acetate
NCI Dictionary Entry. [2005-07-02]. （原始内容存档于2015-05-11）.
Phase 1 Clinical Trials. [2005-07-02]. （原始内容存档于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]. （原始内容存档于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-二羟基-3-(羟甲基)-1,1,6,8-四甲基-5-氧-1a,1b,4,4a,5,7a,7b,8,9,9a-十氢-H-环丙[3,4]苯并[1,2-e]薁-9-肉豆蔻酸酯
别名	TPA，PMA，佛波醇肉豆蔻酰乙酸酯，十四酰佛波乙酯
识别
CAS号	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
性质
化学式	C₃₆H₅₆O₈
摩尔质量	616.83 g·mol⁻¹
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。