12-O-Tetradekanoilforbol-13-acetat

12-O-Tetradekanoilforbol-13-acetat
TPA
IUPAC ime
 
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetiloksi)-4a,7b-dihidroksi-3-(hidroksimetil)-1,1,6,8-tetrametil-5-okso-1a,1b,4,4a,5,7a,7b,8,9,9a-dekahidro-H-ciklopropa[3,4]benzo[1,2-e]azulen-9-il miristat
Drugi nazivi TPA, PMA, Forbol miristat acetat,
Tetradekanoilforbol acetat.
Identifikacija
CAS registarski broj 16561-29-8 DaY
PubChem[1][2] 10475874
ChemSpider[3] 17215855 DaY
KEGG[4] C05151
ChEMBL[5] CHEMBL279115 DaY
Jmol-3D slike Slika 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 DaY
Kod: PHEDXBVPIONUQT-AOWVHHMZSA-N DaY

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
Kod: PHEDXBVPIONUQT-AOWVHHMZBF

Svojstva
Molekulska formula C36H56O8
Molarna masa 616.83 g mol−1

 DaY (šta je ovo?)   (verifikuj)

Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala

Infobox references

12-O-tetradekanoilforbol-13-acetat (TPA) (tetradekanoilforbol acetat, tetradekanoil forbol acetat, forbol 12-miristat 13-acetat, PMA) je diestar forbola i potentan promoter tumora koji se često koristi u biomedicinskim istraživanjima za aktiviranje prenosa signala enzima proteinska kinaza C (PKC).[6][7][8] TPA deluje na PKC usled njegove sličnosti sa prirodnim aktivatorom klasičnih PKC izoformi, diacilglicerolom.

TPA se istražuje kao potencijalni lek za tretman hematološkog kancera.

Reference

  1. ↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.  edit
  2. ↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1. 
  3. ↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846.  edit
  4. ↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H. 
  5. ↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594.  edit
  6. ↑ Castagna et al (1982). „Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters”. Journal of Biological Chemistry 257 (13): 7847–7851. 
  7. ↑ Blumberg (1988). „Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture”. Cancer Research 48: 1–8. 
  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. 

Spoljašnje veze

Portal Hemija
  • MeSH Tetradecanoylphorbol+Acetate
  • „NCI Dictionary Entry”. Arhivirano iz originala na datum 2005-09-01. Pristupljeno 02. 07. 2005. 
  • „Phase 1 Clinical Trials”. Pristupljeno 02. 07. 2005.