Quinalizarin

Quinalizarin
Names
	Preferred IUPAC name 1,2,5,8-Tetrahydroxyanthracene-9,10-dione
Identifiers
CAS Number	81-61-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL29898 ;
ChemSpider	4829 ;
ECHA InfoCard	100.001.243
PubChem CID	5004;
UNII	6D43C3LYSG ;
CompTox Dashboard (EPA)	DTXSID4052558 ;
	InChI 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 Key: VBHKTXLEJZIDJF-UHFFFAOYSA-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;
	SMILES C1=CC(=C(C2=C1C(=O)C3=C(C=CC(=C3C2=O)O)O)O)O;
Properties
Chemical formula	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).
	(what is ?)
	Infobox references

Quinalizarin or 1,2,5,8-tetrahydroxyanthraquinone is an organic compound with formula C
₁₄H
₈O
₆. It is one of many tetrahydroxyanthraquinone isomers, formally derived from anthraquinone by replacement of four hydrogen atoms by hydroxyl (OH) groups.

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]

References[]

^ 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.
^ 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.
^ 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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[zz-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.

[pmid6325410-2] 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.

[pmid8180106-3] 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.

[1]

[2]

[3]

Quinalizarin

See also[]

References[]