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Q2763

Sigma-Aldrich

Quinalizarin

≥95% (HPLC), powder, plasmodium falciparum casein kinase 2α (PfCK2α) inhibitor

Synonym(s):

1,2,5,8-Tetrahydroxy-9,10-anthraquinone, 1,2,5,8-Tetrahydroxyanthraquinone, Alizarin Bordeaux BD, Alizarinbordeaux, Alizarine Bordeaux, Alizarine Bordeaux B, C.I. 58500, C.I. Mordant Violet 26, Khinalizarin, NSC 144046, NSC 4896, PHF 016

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About This Item

Empirical Formula (Hill Notation):
C14H8O6
CAS Number:
81-61-8
Molecular Weight:
272.21
Colour Index Number:
58500
Beilstein:
1889617
EC Number:
201-366-6
MDL number:
MFCD00001205
UNSPSC Code:
12171500
PubChem Substance ID:
329823863
NACRES:
NA.77

product name

Quinalizarin, ≥95% (HPLC)

Assay

≥95% (HPLC)

form

powder

color

red

mp

≥300 °C

storage temp.

room temp

SMILES string

Oc1ccc2C(=O)c3c(O)ccc(O)c3C(=O)c2c1O

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

InChI key

VBHKTXLEJZIDJF-UHFFFAOYSA-N

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Application

Quinalizarin has been used:
  • as a casein kinase II (CKII) inhibitor to study its effect on CKII-mediated phosphorylation of importin α on subcellular scaling in sperm chromosomes and egg extract
  • as a CKII inhibitor to study its ability to block parasite multiplication in a [3H]-hypoxanthine incorporation assay
  • to study its effect on colorectal cancer (CRC) cell cycle arrest, cell apoptosis, and reactive oxygen species (ROS) generation in SW480 and HCT-116 cell lines

Biochem/physiol Actions

Quinalizarin is a potent (IC50 = 110 nM), ATP-competitive, and highly selective (IC50 >1μM against CK1 and 72 other kinases) casein Kinase II (CK2) inhibitor.
Studies show that quinalizarin can prevent the in vitro activity of recombinant Plasmodium falciparum casein kinase 2α (PfCK2α) catalytic subunit with an IC50 of 2μM.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Y Zhou et al.
Indian journal of cancer, 52 Suppl 2, e119-e124 (2016-01-06)
Protein kinase CK2 is widely expressed in eukaryotic cells, and plays an important role in cell proliferation, migration, apoptosis, etc. The aim of the current study is to explore how Quinalizarin, a specific CK2 inhibitor, affects the cell proliferation, migration
Marina Willibald et al.
Oncotarget, 8(42), 72480-72493 (2017-10-27)
Menopausal hormone therapy, using estrogen and synthetic progestins, is associated with an increased risk of developing breast cancer. The effect of progestins on breast cells is complex and not yet fully understood. In previous
Ling-Qi Meng et al.
Medical science monitor : international medical journal of experimental and clinical research, 24, 3710-3719 (2018-06-04)
BACKGROUND Quinalizarin (1,2,5,8-tetrahydroxyanthraquinone) exhibits potentially useful anticancer effects by inducing apoptosis in several types of cancer, but its underlying mechanism of action remains unknown. The present study examined the effects of quinalizarin on the induction of cell cycle arrest, apoptosis
Yinpeng Jin et al.
EBioMedicine, 34, 231-242 (2018-08-06)
It has previously been reported that human adipose-derived stem cells (hASCs) can promote the regeneration of damaged tissues in rats with liver failure through a 'paracrine effect'. Here we demonstrate a therapeutic effect of hASCs derived Extracellular Vesicles (EVs) on
Mohammad S Zaman et al.
Metallomics : integrated biometal science, 8(1), 82-90 (2015-12-02)
Protein kinase CK2 is a pleiotropic tetrameric enzyme, regulating numerous biological processes from cell proliferation to stress response. This study demonstrates for the first time that CK2 is involved in the regulation of metal uptake and toxicity in neuronal cells.
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