Définitions et usages de : 12-O-Tetradecanoylphorbol-13-acetate

Définition

⇨ voir la définition de Wikipedia

Publicité ▼

Wikipedia

12-O-Tetradecanoylphorbol-13-acetate

12-O-Tetradecanoylphorbol-13-acetate

IUPAC name (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
Other names TPA, PMA, Phorbol myristate acetate, Tetradecanoylphorbol acetate.
Identifiers
CAS number	16561-29-8^Y
PubChem	10475874
ChemSpider	17215855^Y
KEGG	C05151^N
ChEMBL	CHEMBL279115^N
Jmol-3D images	Image 1
SMILES 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 InChI=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^Y Key: PHEDXBVPIONUQT-AOWVHHMZSA-N^Y 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 Key: PHEDXBVPIONUQT-AOWVHHMZBF
Properties
Molecular formula	C₃₆H₅₆O₈
Molar mass	616.83 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Not to be confused with tissue plasminogen activator (tPA), an enzyme.

12-O-tetradecanoylphorbol-13-acetate (TPA), also commonly known as tetradecanoylphorbol acetate, tetradecanoyl phorbol acetate, and phorbol 12-myristate 13-acetate (PMA), is 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.

TPA is also being studied as a drug in the treatment of hematologic cancer.

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.^[4]

TPA was first found in the croton plant, a shrub found in Southeast Asia, exposure to which provokes a poison ivy-like rash. It underwent a phase 1 clinical trial.

References

^ Castagna et al (1982). Journal of Biological Chemistry 257 (13): 7847–7851.
^ Blumberg (1988). Cancer Research 48: 1–8.
^ Niedel et al (1983). "Phorbol Diester Receptor Copurifies with Protein Kinase C". Proceedings of the National Academy of Sciences 80: 36–40. DOI:10.1073/pnas.80.1.36.
^ The AGT cytogenetics laboratory manual. 3rd ed. Barch, Margaret J., Knutsen, Turid., Spurbeck, Jack L., eds. 1997. Lippincott-Raven.

External links

Tetradecanoylphorbol+Acetate at the US National Library of Medicine Medical Subject Headings (MeSH)
"NCI Dictionary Entry". http://www.cancer.gov/Templates/db_alpha.aspx?CdrID=46763. Retrieved 2005-07-02.
"Phase 1 Clinical Trials". http://www.clinicaltrials.gov/ct/show/NCT00004058. Retrieved 2005-07-02.

Retrieved from "http://en.wikipedia.org/w/index.php?title=12-O-Tetradecanoylphorbol-13-acetate&oldid=489284572"

Categories:

This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)

Donate to Wikimedia

Significations et usages de 12-O-Tetradecanoylphorbol-13-acetate

Définition

12-O-Tetradecanoylphorbol-13-acetate

References

External links