Quinalizarin: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 400630960

| ImageFile = Quinalizarin.svg

| ImageSize = 200px

| ImageName = Skeletal formula of quinalizarin

| ImageSize1 = 200px

| ImageName1 = Ball-and-stick model

| PIN = 1,2,5,8-Tetrahydroxyanthracene-9,10-dione

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 81-61-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6D43C3LYSG

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 29898

| PubChem = 5004

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4829

| SMILES = C1=CC(=C(C2=C1C(=O)C3=C(C=CC(=C3C2=O)O)O)O)O

| 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

| InChIKey = VBHKTXLEJZIDJF-UHFFFAOYAM

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = VBHKTXLEJZIDJF-UHFFFAOYSA-N}}

|Section2={{Chembox Properties

| C=14 | H=8 | O=6

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

{{distinguish|text = quinizarin, a [[dihydroxyanthraquinone]]}}

'''Quinalizarin''' or '''1,2,5,8-tetrahydroxyanthraquinone''' is an [[organic compound]] with formula {{chem2|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]].<ref name=zz>{{ cite journal |author1=Cozza, G. |author2=Mazzorana, M. |author3=Papinutto, E. |author4=Bain, J. |author5=Elliott, M. |author6=di Maira, G. |author7=Gianoncelli, A. |author8=Pagano, M. A. |author9=Sarno, S. |author10=Ruzzene, M. |author11=Battistutta, R. |author12=Meggio, F. |author13=Moro, S. |author14=Zagotto, G. |author15=Pinna, L. A. | title = Quinalizarin as a Potent, Selective and Cell-Permeable Inhibitor of Protein Kinase CK2 | journal = The Biochemical Journal | year = 2009 | volume = 421 | issue = 3 | pages = 387–395 | doi = 10.1042/BJ20090069 | pmid = 19432557 |url=https://hal.archives-ouvertes.fr/hal-00479150/file/PEER_stage2_10.1042%252FBJ20090069.pdf }}</ref> It is also a potent [[catechol O-methyltransferase inhibitor|catechol O-methyltransferase (COMT) inhibitor]].<ref name="pmid6325410">{{cite journal | vauthors = Schneider J, Huh MM, Bradlow HL, Fishman J | title = Antiestrogen action of 2-hydroxyestrone on MCF-7 human breast cancer cells | journal = J. Biol. Chem. | volume = 259 | issue = 8 | pages = 4840–5 | date = April 1984 | pmid = 6325410 | url = https://www.jbc.org/content/259/8/4840.short}}</ref><ref name="pmid8180106">{{cite journal | vauthors = Schütze N, Vollmer G, Knuppen R | title = Catecholestrogens are agonists of estrogen receptor dependent gene expression in MCF-7 cells | journal = J. Steroid Biochem. Mol. Biol. | volume = 48 | issue = 5-6 | pages = 453–61 | date = April 1994 | pmid = 8180106 | doi = 10.1016/0960-0760(94)90193-7 }}</ref>

* [[Alizarin]], a related simpler dye

{{Reflist}}

{{Monoamine metabolism modulators}}

[[Category:3-Hydroxypropenals]]

[[Category:Catechol-O-methyltransferase inhibitors]]

[[Category:Hydroquinones]]

[[Category:Tetrahydroxyanthraquinones]]

{{Ketone-stub}}