From Wikipedia, the free encyclopedia
Quinalizarin
Names
Preferred IUPAC name
1,2,5,8-Tetrahydroxyanthracene-9,10-dione
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard
100.001.243
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
C 14 H 8 O 6
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).
Chemical compound
Quinalizarin or 1,2,5,8-tetrahydroxyanthraquinone is an
organic compound with formula C14 H8 O6 . 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
^ 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 .