Quinalizarin - Wikipedia

Quinalizarin
Names


Preferred IUPAC name 1,2,5,8-Tetrahydroxyanthracene-9,10-dione
Identifiers
CAS Number	81-61-8^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL29898^N
ChemSpider	4829^N
ECHA InfoCard	100.001.243
PubChem CID	5004
UNII	6D43C3LYSG^Y
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^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
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). N verify (what is ^YN ?) 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.

Monoamine metabolism modulators

Non-specific

AAAD

Substrates→Products: L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine

MAO

Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR): Epinephrine (adrenaline)→DHMA Metanephrine→MHPG/VMA Norepinephrine (noradrenaline)→DHMA Normetanephrine→MHPG/VMA Dopamine→DOPAC 3-Methoxytyramine→HVA Serotonin→5-HIAA Inhibitors: Non-selective: Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine
Inhibitors: MAO-A-selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone
Inhibitors: MAO-B selective: Adarigiline Almoxatone D-Deprenyl Desmethylselegiline Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl) Sembragiline Tisolagiline

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products: Phenylalanine→Tyrosine Inhibitors: 3,4-Dihydroxystyrene
THTooltip Tyrosine hydroxylase	Substrates→Products: Tyrosine→L-DOPA (levodopa) Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone
DBHTooltip Dopamine beta-monooxygenase	Substrates→Products: Dopamine→Norepinephrine (Noradrenaline) Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone
PNMTTooltip Phenylethanolamine N-methyltransferase	Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline) Inhibitors: CGS-19281A SKF-64139 SKF-7698
COMTTooltip Catechol-O-methyl transferase	Substrates→Products: Dopamine→3-Methoxytyramine DOPAC→Homovanillic acid Norepinephrine→Normetanephrine Epinephrine→Metanephrine DOPEG→MOPEG DOMA→VMA 2-Hydroxyestradiol→2-Methoxyestradiol 2-Hydroxyestrone→2-Methoxyestrone 4-Hydroxyestradiol→4-Methoxyestradiol 4-Hydroxyestrone→4-Methoxyestrone Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Neluxicapone Nitecapone Opicapone Quinalizarin Tolcapone

Tryptamines
(serotonin, melatonin)

TPHTooltip Tryptophan hydroxylase	Substrates→Products: Tryptophan→5-HTP Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat ethyl
AANATTooltip Serotonin N-acetyl transferase	Substrates→Products: Serotonin→N-Acetylserotonin
ASMTTooltip Acetylserotonin O-methyltransferase	Substrates→Products: N-Acetylserotonin→Melatonin

Histamine

HDCTooltip Histidine decarboxylase	Substrates→Products: L-Histidine→Histamine Inhibitors: Catechin Alpha-Fluoromethylhistidine Histidine methyl ester Meciadanol Naringenin Tritoqualine
HNMTTooltip Histamine N-methyltransferase	Substrates→Products: Histamine→N-Methylhistamine Inhibitors: Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91488 Tacrine
DAOTooltip Diamine oxidase	Substrates→Products: Histamine→Imidazole acetic acid Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins

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