佛波醇-12-十四烷酰-13-乙酸酯

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。

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
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  checkY
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。

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而非离子霉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]

細胞遺傳學試驗中,TPA被視為B細胞淋巴瘤細胞的有丝分裂原,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细胞白血病血液癌症[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,亦可用作细胞内染色的助劑。[7]

参考文献

  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.
  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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