Quinalizarin

Quinalizarin
Skeletal formula of quinalizarin
Ball-and-stick model
Names
Preferred IUPAC name
1,2,5,8-Tetrahydroxyanthracene-9,10-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.243 Edit this at Wikidata
UNII
  • InChI=1S/C14H8O6/c15-6-3-4-7(16)11-10(6)12(18)5-1-2-8(17)13(19)9(5)14(11)20/h1-4,15-17,19H ☒N
    Key: VBHKTXLEJZIDJF-UHFFFAOYSA-N ☒N
  • InChI=1/C14H8O6/c15-6-3-4-7(16)11-10(6)12(18)5-1-2-8(17)13(19)9(5)14(11)20/h1-4,15-17,19H
    Key: VBHKTXLEJZIDJF-UHFFFAOYAM
  • C1=CC(=C(C2=C1C(=O)C3=C(C=CC(=C3C2=O)O)O)O)O
Properties
C14H8O6
Molar mass 272.212 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Not to be confused with quinizarin, a dihydroxyanthraquinone.

Quinalizarin or 1,2,5,8-tetrahydroxyanthraquinone is an organic compound with formula C12H4(OH)4(CO)2. It is one of many tetrahydroxyanthraquinone isomers, formally derived from anthraquinone by replacement of four hydrogen atoms by hydroxyl (OH) groups at the 1, 2, 5, and 8 positions.

Quinalizarin is an inhibitor of the enzyme protein kinase CK2. It is more potent and selective than emodin.[1] It is also a potent catechol O-methyltransferase (COMT) inhibitor.[2][3]

See also

References

  1. ^ Cozza, G.; Mazzorana, M.; Papinutto, E.; Bain, J.; Elliott, M.; di Maira, G.; Gianoncelli, A.; Pagano, M. A.; Sarno, S.; Ruzzene, M.; Battistutta, R.; Meggio, F.; Moro, S.; Zagotto, G.; Pinna, L. A. (2009). "Quinalizarin as a Potent, Selective and Cell-Permeable Inhibitor of Protein Kinase CK2" (PDF). The Biochemical Journal. 421 (3): 387–395. doi:10.1042/BJ20090069. PMID 19432557.
  2. ^ Schneider J, Huh MM, Bradlow HL, Fishman J (April 1984). "Antiestrogen action of 2-hydroxyestrone on MCF-7 human breast cancer cells". J. Biol. Chem. 259 (8): 4840–5. PMID 6325410.
  3. ^ Schütze N, Vollmer G, Knuppen R (April 1994). "Catecholestrogens are agonists of estrogen receptor dependent gene expression in MCF-7 cells". J. Steroid Biochem. Mol. Biol. 48 (5–6): 453–61. doi:10.1016/0960-0760(94)90193-7. PMID 8180106.



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