| 词条 | 12-O-Tetradecanoylphorbol-13-acetate |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477208864 | Name = 12-O-Tetradecanoylphorbol-13-acetate | ImageFile = 12-O-Tetradecanoylphorbol-13-acetate.svg | ImageSize = 300px | ImageName = TPA | IUPACName =(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate | OtherNames = TPA, PMA, Phorbol myristate acetate, Tetradecanoylphorbol acetate. | Section1 = {{Chembox Identifiers | IUPHAR_ligand = 2341 | PubChem = 27924 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 25977 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 37537 | 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 | SMILES2 = CCCCCCCCCCCCCC(=O)O[C@@H]2C(C)[C@]1(O)C4/C=C(/C)C(=O)[C@@]4(O)CC(\\CO)=C/[C@H]1[C@H]3[C@]2(OC(C)=O)C3(C)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 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = PHEDXBVPIONUQT-RGYGYFBISA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 16561-29-8 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 279115 | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C05151 | Section2 = {{Chembox Properties |C=36|H=56|O=8 | MolarMass = 616.83 g/mol }} 12-O-Tetradecanoylphorbol-13-acetate (TPA), also commonly known as tetradecanoylphorbol acetate, tetradecanoyl phorbol acetate, and phorbol 12-myristate 13-acetate (PMA), is a diester of phorbol and a potent tumor promoter often employed in biomedical research to activate the signal transduction enzyme protein kinase C (PKC).[1][2][3] The effects of TPA on PKC result from its similarity to one of the natural activators of classic PKC isoforms, diacylglycerol. TPA is a small molecule drug. In ROS biology, superoxide was identified as the major reactive oxygen species induced by TPA/PMA but not by ionomycin in mouse macrophages.[4] Thus, TPA/PMA has been routinely used as an inducer for endogenous superoxide production.[5] TPA is also being studied as a drug in the treatment of hematologic cancer {{citation needed|date=November 2015}} TPA has a specific use in cancer diagnostics as a B-cell specific mitogen in cytogenetic testing. To view the chromosomes, a cytogenetic test requires dividing cells. TPA is used to stimulate division of B-cells during cytogenetic diagnosis of B-cell cancers such as chronic lymphocytic leukemia.[6] TPA is also commonly used together with ionomycin to stimulate T-cell activation, proliferation, and cytokine production, and is used in protocols for intracellular staining of these cytokines.[7] TPA induces KSHV reactivation in PEL cell cultures via stimulation of the mitogen-activated protein kinase (MAPK)/extracellular signal-regulated kinase (ERK) pathway. The pathway involves the activation of the early-immediate viral protein RTA that contributes to the activation of the lytic cycle.[8] TPA was first found in the croton plant, a shrub found in Southeast Asia, exposure to which provokes a poison ivy-like rash.{{Citation needed| date=December 2012}} It underwent a phase 1 clinical trial.{{citation needed|date=April 2018}} References1. ^{{cite journal | last1= Castagna | year = 1982 |title=Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters |url=http://www.jbc.org/content/257/13/7847.full.pdf | journal = Journal of Biological Chemistry | volume = 257 | issue = 13 | pages = 7847–7851 |pmid=7085651}} 2. ^{{cite journal | last1= Blumberg | year = 1988 |title= Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture| journal = Cancer Research | volume = 48 | issue = | pages = 1–8| pmid = 3275491}} 3. ^{{cite journal | last1= Niedel | year = 1983 | journal = Proceedings of the National Academy of Sciences | volume = 80 | pages = 36–40 | doi = 10.1073/pnas.80.1.36 | title = Phorbol Diester Receptor Copurifies with Protein Kinase C | bibcode = 1983PNAS...80...36N | pmc = 393304 }} 4. ^{{cite journal | last1 = Swindle | year = 2002 |title= 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|url=http://www.jimmunol.org/content/169/10/5866.full.pdf | journal = The Journal of Immunology | volume = 169 | issue = 10 | pages = 5866–5873 |doi=10.4049/jimmunol.169.10.5866}} 5. ^{{cite journal | last1= Huang | year = 2014 |title=Megakaryocytic Differentiation of K562 Cells Induced by PMA Reduced the Activity of Respiratory Chain Complex IV | journal = PLoS ONE | volume = 9 | issue = 5 | pages = e96246 |doi=10.1371/journal.pone.0096246| bibcode=2014PLoSO...996246H }} 6. ^The AGT cytogenetics laboratory manual. 3rd ed. Barch, Margaret J., Knutsen, Turid., Spurbeck, Jack L., eds. 1997. Lippincott-Raven. 7. ^{{cite web | url = http://www.ebioscience.com/resources/best-protocols/flow-cytometry/flow-cytometry-intracellular-staining-quick-guide.htm | title = Flow Cytometry Intracellular Staining Guide | date = | work = | publisher = eBioscience, Inc | accessdate = 2011-09-25 }} 8. ^{{cite journal|last1=Cohen|first1=Adina|last2=Brodie|first2=Chaya|last3=Sarid|first3=Ronit|title=An essential role of ERK signalling in TPA-induced reactivation of Kaposi's sarcoma-associated herpesvirus.|journal=The Journal of General Virology|date=April 2006|volume=87|issue=Pt 4|pages=795–802|pmid=16528027|url=http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.321.5484&rep=rep1&type=pdf|doi=10.1099/vir.0.81619-0}} External links
6 : Diterpenes|Carcinogens|Acetate esters|Cyclopropanes|Cyclopentenes|Phorbol esters |
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