Quinalizarin

Chemical compound

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

• 1,4-Dihydroxyanthraquinone (quinizarin)
• Alizarin, a related simpler dye

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.