Quinalizarin | CAS#81-61-8 | CK2 inhibitor

MedKoo Cat#: 563606 | Name: Quinalizarin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Quinalizarin is a potent, selective and cell-permeable protein kinase CK2 inhibitor. Quinalizarin can induce apoptosis of certain cancer cells. Quinalizarin is a potential antifungal drug for the treatment of Candida albicans fungal infection in cancer patients.

Chemical Structure

Quinalizarin

CAS#81-61-8

Theoretical Analysis

MedKoo Cat#: 563606

Name: Quinalizarin

CAS#: 81-61-8

Chemical Formula: C14H8O6

Exact Mass: 272.0321

Molecular Weight: 272.21

Elemental Analysis: C, 61.77; H, 2.96; O, 35.26

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks
25mg	USD 1,050.00	2 Weeks

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Related CAS #

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Synonym

Alizarin Bordeaux BD; Alizarinbordeaux; Alizarine Bordeaux; Alizarine Bordeaux B; C.I. 58500; C.I. Mordant Violet 26; Khinalizarin; NSC 144046; NSC 4896; PHF 016; Quinalizarine; Quinazarin;

IUPAC/Chemical Name

1,2,5,8-Tetrahydroxyanthraquinone

InChi Key

VBHKTXLEJZIDJF-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=C(C1=C2C(O)=CC=C1O)C3=CC=C(O)C(O)=C3C2=O

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Quinalizarin is a potent, selective and cell-permeable protein kinase CK2 inhibitor with an Ki of ~50 nM and an IC50 of 110 nM.

In vitro activity:

Human nasopharyngeal carcinoma (NPC) cell lines CNE-1, CNE-2 and 5-8F were treated with quinalizarin and then irradiated with different X-rays doses. Quinalizarin at 25 µM enhanced radiosensitivity of NPC cells. This increased radiosensitivity was due to inhibition of cell viability, which delayed DSB repair, promoting apoptosis by 34% in CNE-1 and 9% in CNE-2 cells and changing cell cycle distribution in CNE-1 cells. Quinalizarin enhanced radiosensitivity of NPC cells partially by suppressing SHP-1 expression. Reference: Int J Oncol. 2016 Mar;48(3):1073-84. https://pubmed.ncbi.nlm.nih.gov/29170453/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 272.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Li Q, Li K, Yang T, Zhang S, Zhou Y, Li Z, Xiong J, Zhou F, Zhou X, Liu L, Meng R, Wu G. Association of protein kinase CK2 inhibition with cellular radiosensitivity of non-small cell lung cancer. Sci Rep. 2017 Nov 23;7(1):16134. doi: 10.1038/s41598-017-16012-1. PMID: 29170453; PMCID: PMC5700935. 2. Pan X, Meng R, Yu Z, Mou J, Liu S, Sun Z, Zou Z, Wu G, Peng G. Quinalizarin enhances radiosensitivity of nasopharyngeal carcinoma cells partially by suppressing SHP-1 expression. Int J Oncol. 2016 Mar;48(3):1073-84. doi: 10.3892/ijo.2016.3338. Epub 2016 Jan 14. PMID: 26781335.

In vitro protocol:

In vivo protocol:

TBD

1: Janeczko M, Kochanowicz E, Górka K, Skrzypek T. Quinalizarin as a potential antifungal drug for the treatment of Candida albicans fungal infection in cancer patients. Microbiol Spectr. 2024 Jan 30;12(3):e0365223. doi: 10.1128/spectrum.03652-23. Epub ahead of print. PMID: 38289929; PMCID: PMC10913734. 2: Chatterjee S, Jain CK, Saha T, Roychoudhury S, Majumder HK, Das S. Utilizing coordination chemistry through formation of a CuII-quinalizarin complex to manipulate cell biology: An in vitro, in silico approach. J Inorg Biochem. 2023 Dec;249:112369. doi: 10.1016/j.jinorgbio.2023.112369. Epub 2023 Sep 21. PMID: 37776829. 3: Lauro FV, Marcela RN, Maria LR, Magdalena AR, Virginia MM, Francisco DC, Alejandra GE, Tomas LG, Montserrat MG. Evaluation of Biological Activity of a Diazocine Derivative against Heart Failure Using an Ischemia-Reperfusion Injury Model. Drug Res (Stuttg). 2022 Sep;72(7):404-411. doi: 10.1055/a-1840-3199. Epub 2022 Jun 20. PMID: 35724672. 4: Zhang L, Ruan X, Gu M, Mueck AO. E2 + norethisterone promotes the PI3K-AKT pathway via PGRMC1 to induce breast cancer cell proliferation. Climacteric. 2022 Oct;25(5):467-475. doi: 10.1080/13697137.2022.2029837. Epub 2022 Feb 9. PMID: 35137666. 5: Tran NNQ, Chun KH. ROCK2-Specific Inhibitor KD025 Suppresses Adipocyte Differentiation by Inhibiting Casein Kinase 2. Molecules. 2021 Aug 5;26(16):4747. doi: 10.3390/molecules26164747. PMID: 34443331; PMCID: PMC8401933. 6: Zang YQ, Zhai YQ, Feng YY, Ju XY, Zuo F. Molecular mechanisms of quinalizarin induces apoptosis and G0/G1 cell cycle of human esophageal cancer HCE-4 cells depends on MAPK, STAT3, and NF-κB signaling pathways. Environ Toxicol. 2021 Feb;36(2):276-286. doi: 10.1002/tox.23033. Epub 2020 Oct 8. PMID: 33030807. 7: Ahmed MH, Aldesouki HM, Badria FA. Effect of phenolic compounds from the leaves of Psidium guajava on the activity of three metabolism-related enzymes. Biotechnol Appl Biochem. 2021 Jun;68(3):497-512. doi: 10.1002/bab.1956. Epub 2020 May 26. PMID: 32432341. 8: Ilkar Erdagi S, Ngwabebhoh FA, Yildiz U. Pickering stabilized nanocellulose- alginate: A diosgenin-mediated delivery of quinalizarin as a potent cyto- inhibitor in human lung/breast cancer cell lines. Mater Sci Eng C Mater Biol Appl. 2020 Apr;109:110621. doi: 10.1016/j.msec.2019.110621. Epub 2020 Jan 20. PMID: 32228903. 9: Zang YQ, Feng YY, Luo YH, Zhai YQ, Ju XY, Feng YC, Sheng YN, Wang JR, Yu CQ, Jin CH. Quinalizarin induces ROS‑mediated apoptosis via the MAPK, STAT3 and NF‑κB signaling pathways in human breast cancer cells. Mol Med Rep. 2019 Nov;20(5):4576-4586. doi: 10.3892/mmr.2019.10725. Epub 2019 Oct 2. PMID: 31702038; PMCID: PMC6798002. 10: Mukherjee Chatterjee S, Jain CK, Singha S, Das P, Roychoudhury S, Majumder HK, Das S. Activity of CoII-Quinalizarin: A Novel Analogue of Anthracycline-Based Anticancer Agents Targets Human DNA Topoisomerase, Whereas Quinalizarin Itself Acts via Formation of Semiquinone on Acute Lymphoblastic Leukemia MOLT-4 and HCT 116 Cells. ACS Omega. 2018 Aug 30;3(8):10255-10266. doi: 10.1021/acsomega.8b00706. PMID: 31459155; PMCID: PMC6644896. 11: Luo YH, Li JQ, Zhang Y, Wang JR, Xu WT, Zhang Y, Feng YC, Li SZ, Jin CH. Quinalizarin induces cycle arrest and apoptosis via reactive oxygen species- mediated signaling pathways in human melanoma A375 cells. Drug Dev Res. 2019 Dec;80(8):1040-1050. doi: 10.1002/ddr.21582. Epub 2019 Aug 20. PMID: 31432559. 12: Li K, Zhou F, Zhou Y, Zhang S, Li Q, Li Z, Liu L, Wu G, Meng R. Quinalizarin, a specific CK2 inhibitor, can reduce icotinib resistance in human lung adenocarcinoma cell lines. Int J Mol Med. 2019 Aug;44(2):437-446. doi: 10.3892/ijmm.2019.4220. Epub 2019 May 30. PMID: 31173177; PMCID: PMC6605624. 13: Li Q, Zong Y, Li K, Jie X, Hong J, Zhou X, Wu B, Li Z, Zhang S, Wu G, Meng R. Involvement of endothelial CK2 in the radiation induced perivascular resistant niche (PVRN) and the induction of radioresistance for non-small cell lung cancer (NSCLC) cells. Biol Res. 2019 Apr 16;52(1):22. doi: 10.1186/s40659-019-0231-x. PMID: 30992075; PMCID: PMC6466699. 14: Meng LQ, Wang Y, Luo YH, Piao XJ, Liu C, Wang Y, Zhang Y, Wang JR, Wang H, Xu WT, Liu Y, Wu YQ, Sun HN, Han YH, Jin MH, Shen GN, Fang NZ, Jin CH. Quinalizarin Induces Apoptosis through Reactive Oxygen Species (ROS)-Mediated Mitogen-Activated Protein Kinase (MAPK) and Signal Transducer and Activator of Transcription 3 (STAT3) Signaling Pathways in Colorectal Cancer Cells. Med Sci Monit. 2018 Jun 3;24:3710-3719. doi: 10.12659/MSM.907163. PMID: 29860266; PMCID: PMC6014151. 15: Meng LQ, Liu C, Luo YH, Piao XJ, Wang Y, Zhang Y, Wang JR, Wang H, Xu WT, Liu Y, Wu YQ, Sun HN, Han YH, Jin MH, Shen GN, Zang YQ, Li J, Fang NZ, Cui YD, Jin CH. Quinalizarin exerts an anti-tumour effect on lung cancer A549 cells by modulating the Akt, MAPK, STAT3 and p53 signalling pathways. Mol Med Rep. 2018 Feb;17(2):2626-2634. doi: 10.3892/mmr.2017.8110. Epub 2017 Nov 20. PMID: 29207064. 16: Li Q, Li K, Yang T, Zhang S, Zhou Y, Li Z, Xiong J, Zhou F, Zhou X, Liu L, Meng R, Wu G. Association of protein kinase CK2 inhibition with cellular radiosensitivity of non-small cell lung cancer. Sci Rep. 2017 Nov 23;7(1):16134. doi: 10.1038/s41598-017-16012-1. PMID: 29170453; PMCID: PMC5700935. 17: Willibald M, Bayer G, Stahlhut V, Poschmann G, Stühler K, Gierke B, Pawlak M, Seeger H, Mueck AO, Niederacher D, Fehm T, Neubauer H. Progesterone receptor membrane component 1 is phosphorylated upon progestin treatment in breast cancer cells. Oncotarget. 2017 Aug 2;8(42):72480-72493. doi: 10.18632/oncotarget.19819. PMID: 29069804; PMCID: PMC5641147. 18: Schwind L, Nalbach L, Zimmer AD, Kostelnik KB, Menegatti J, Grässer F, Götz C, Montenarh M. Quinalizarin inhibits adipogenesis through down-regulation of transcription factors and microRNA modulation. Biochim Biophys Acta Gen Subj. 2017 Dec;1861(12):3272-3281. doi: 10.1016/j.bbagen.2017.09.018. Epub 2017 Sep 28. PMID: 28964816. 19: Mohamed ME, Frag EYZ, Hathoot AA, Shalaby EA. Spectrophotometric determination of fenoprofen calcium drug in pure and pharmaceutical preparations. Spectroscopic characterization of the charge transfer solid complexes. Spectrochim Acta A Mol Biomol Spectrosc. 2018 Jan 15;189:357-365. doi: 10.1016/j.saa.2017.08.027. Epub 2017 Aug 10. PMID: 28830039. 20: Liu C, Luo YH, Piao XJ, Wang Y, Meng LQ, Wang H, Wang JR, Zhang Y, Li JQ, Jin CH. [Quinalizarin induces apoptosis in gastric cancer AGS cells via MAPK and Akt signaling pathway]. Nan Fang Yi Ke Da Xue Xue Bao. 2017 Aug 20;37(8):1085-1091. Chinese. doi: 10.3969/j.issn.1673-4254.2017.08.14. PMID: 28801290; PMCID: PMC6765738.