| Revision as of 16:48, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472989359 of page 12-O-Tetradecanoylphorbol-13-acetate for the Chem/Drugbox validation project (updated: 'ChEMBL', 'KEGG'). |
Latest revision as of 06:04, 12 August 2023 edit GabbyTheDarkAlien (talk | contribs)Extended confirmed users752 edits Fixed sentence structure to make it more clear and fixed some grammar mistakesTag: Visual edit |
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{{DISPLAYTITLE:12-''O''-Tetradecanoylphorbol-13-acetate}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 444906850 |
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| verifiedrevid = 477208864 |
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| Name = 12-''O''-Tetradecanoylphorbol-13-acetate |
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| Name = 12-''O''-Tetradecanoylphorbol-13-acetate |
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| ImageFile = 12-O-Tetradecanoylphorbol-13-acetate.svg |
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| ImageFile = 12-O-Tetradecanoylphorbol-13-acetate.svg |
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| ImageSize = 300px |
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| ImageSize = 300px |
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| ImageName = TPA |
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| ImageName = TPA |
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| IUPACName =(1a''R'',1b''S'',4a''R'',7a''S'',7b''S'',8''R'',9''R'',9a''S'')-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''-cyclopropabenzoazulen-9-yl myristate |
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| PIN =(1a''R'',1b''S'',4a''R'',7a''S'',7b''S'',8''R'',9''R'',9a''S'')-4a,7b-Dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9a''H''-cyclopropabenzoazulene-9,9a-diyl 9a-acetate 9-tetradecanoate |
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| OtherNames = TPA, PMA, Phorbol myristate acetate,<br />Tetradecanoylphorbol acetate. |
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| OtherNames = TPA, PMA, Phorbol myristate acetate,<br />Tetradecanoylphorbol acetate. |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| IUPHAR_ligand = 2341 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 27924 |
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| ChemSpiderID = 17215855 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| 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+/m0/s1 |
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⚫ |
| ChemSpiderID = 25977 |
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| InChIKey = PHEDXBVPIONUQT-AOWVHHMZBF |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 37537 |
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| 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+/m0/s1 |
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| SMILES = CCCCCCCCCCCCCC(=O)O1(2((C=C(C3(2C=C(C3=O)C)O)CO)41(C4(C)C)OC(=O)C)O)C |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| SMILES2 = CCCCCCCCCCCCCC(=O)O2C(C)1(O)C4/C=C(/C)C(=O)4(O)CC(\CO)=C/132(OC(C)=O)C3(C)C |
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| StdInChIKey = PHEDXBVPIONUQT-AOWVHHMZSA-N |
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| 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 |
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| InChIKey = PHEDXBVPIONUQT-RGYGYFBIBK |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = PHEDXBVPIONUQT-RGYGYFBISA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 16561-29-8 |
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| CASNo = 16561-29-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = CCCCCCCCCCCCCC(=O)O2C(C)1(O)C4/C=C(/C)C(=O)4(O)CC(\CO)=C/132(OC(C)=O)C3(C)C |
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| PubChem = 10475874 |
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| UNII = NI40JAQ945 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 279115 --> |
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| ChEMBL = 279115 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = <!-- blanked - oldvalue: C05151 --> |
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| KEGG = C05151 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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|C=36|H=56|O=8 |
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|C=36|H=56|O=8 |
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'''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 ]. It is a potent ] often employed in biomedical research to activate the ] ] ] (PKC).<ref>{{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 = ] | volume = 257 | issue = 13 | pages = 7847–7851 | doi = 10.1016/S0021-9258(18)34459-4 |pmid=7085651| doi-access = free }}</ref><ref>{{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 = ] | volume = 48 | issue = 1| pages = 1–8| pmid = 3275491}}</ref><ref>{{cite journal | last1= Niedel | year = 1983 | journal = ] | volume = 80 | pages = 36–40 | doi = 10.1073/pnas.80.1.36 | title = Phorbol Diester Receptor Copurifies with Protein Kinase C | issue = 1 | bibcode = 1983PNAS...80...36N | pmc = 393304 | pmid=6296873| doi-access = free }}</ref> The effects of TPA on PKC result from its similarity to one of the natural activators of classic PKC isoforms, ]. TPA is a ] drug. |
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In ] biology, ] was identified as the major reactive oxygen species induced by TPA/PMA but not by ] in mouse macrophages.<ref>{{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 = ] | volume = 169 | issue = 10 | pages = 5866–5873 |doi=10.4049/jimmunol.169.10.5866| pmid = 12421969 | s2cid = 21433304 | doi-access = free }}</ref> Thus, TPA/PMA has been routinely used as an inducer for endogenous ] production.<ref>{{cite journal | last1= Huang | year = 2014 |title=Megakaryocytic Differentiation of K562 Cells Induced by PMA Reduced the Activity of Respiratory Chain Complex IV | journal = ] | volume = 9 | issue = 5 | pages = e96246 |doi=10.1371/journal.pone.0096246| bibcode=2014PLoSO...996246H | pmc = 4015910 | pmid=24817082| doi-access = free }}</ref> |
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TPA is also being studied as a ] in the treatment of ] ] {{citation needed|date=November 2015}} |
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TPA has a specific use in cancer diagnostics as a B-cell specific ] in ] testing. Cells must be divided in a cytogenic test to view the chromosomes. TPA is used to stimulate division of B-cells during cytogenetic diagnosis of B-cell cancers such as ].<ref>''The AGT cytogenetics laboratory manual''. 3rd ed. Barch, Margaret J., Knutsen, Turid., Spurbeck, Jack L., eds. 1997. Lippincott-Raven.</ref> |
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TPA is also commonly used together with ] to stimulate T-cell activation, proliferation, and cytokine production, and is used in protocols for intracellular staining of these cytokines.<ref name="urlFlow Cytometry Intracellular Staining Guide">{{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 | publisher = eBioscience, Inc | access-date = 2011-09-25 }}</ref> |
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TPA induces ] 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.<ref>{{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|doi=10.1099/vir.0.81619-0|citeseerx=10.1.1.321.5484}}</ref> |
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TPA was first found in the ] plant, a shrub found in Southeast Asia, exposure to which provokes a ]-like rash.{{Citation needed| date=December 2012}} It underwent a phase 1 ].<ref>{{cite journal |last1=Schaar |first1=Dale |last2=Goodell |first2=Lauri |last3=Aisner |first3=Joseph |last4=Cui |first4=Xiao Xing |last5=Han |first5=Zheng Tao |last6=Chang |first6=Richard |last7=Martin |first7=John |last8=Grospe |first8=Stephanie |last9=Dudek |first9=Liesel |last10=Riley |first10=Joan |last11=Manago |first11=Jacqueline |last12=Lin |first12=Yong |last13=Rubin |first13=Eric H. |last14=Conney |first14=Allan |last15=Strair |first15=Roger K. |title=A phase I clinical trial of 12- O-tetradecanoylphorbol-13-acetate for patients with relapsed/refractory malignancies |journal=Cancer Chemotherapy and Pharmacology |date=June 2006 |volume=57 |issue=6 |pages=789–795 |doi=10.1007/s00280-005-0125-1 |pmid=16231182 |s2cid=33377618 |url=https://link.springer.com/article/10.1007/s00280-005-0125-1 |language=en |issn=1432-0843}}</ref> |
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== References == |
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{{reflist}} |
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== External links == |
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* {{MeshName|Tetradecanoylphorbol+Acetate}} |
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* {{cite web|url=http://www.cancer.gov/dictionary?CdrID=46763|title=NCI Dictionary Entry|access-date=2005-07-02}} |
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* {{cite web|url=http://www.clinicaltrials.gov/ct/show/NCT00004058|title=Phase 1 Clinical Trials|access-date=2005-07-02}} |
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{{DEFAULTSORT:Tetradecanoylphorbol-13-acetate, 12-O-}} |
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