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Submit ReviewChloroquine diphosphate
Description: Antimalarial; inhibits apoptosis and autophagy
Chemical Name: N4-(7-Chloro-4-quinolinyl)-N1,N1-dimethyl-1,4-pentanediamine diphosphate salt
Purity: ≥99% (HPLC)
Biological Activity for Chloroquine diphosphate
Chloroquine diphosphate is an antimalarial drug. Inhibits cell growth and induces cell death in numerous cancer cell lines; inhibits cell proliferation and viability and induces apoptosis in 4T1 mouse breast cancer cells in vitro. Exhibits antimetastatic activity. Also inhibits autophagy via a mechanism distinct from that of 3-methyladenine (Cat. No. 3977). Blocks receptor-mediated endocytosis of mannose-glycoconjugates by macrophages. Inhibits SARS-CoV-2 infection in vitro (EC50 = 1.13 μM). Chloroquine improves efficacy of adeno-associated viral gene transduction in vivo and in vitro, as well as enhancing non-viral gene transfection in breast cancer cells.
Tocris products are for biomedical research use only. They are not intended for human or veterinary use.
Technical Data for Chloroquine diphosphate
| M. Wt | 515.86 |
| Formula | C18H26ClN3·2H3PO4 |
| Storage | Desiccate at RT |
| Purity | ≥99% (HPLC) |
| CAS Number | 50-63-5 |
| PubChem ID | 64927 |
| InChI Key | QKICWELGRMTQCR-UHFFFAOYSA-N |
| Smiles | CCN(CC)CCCC(C)NC2=CC=NC1=CC(Cl)=CC=C12.O=P(O)(O)O.O=P(O)(O)O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Chloroquine diphosphate
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 51.59 | 100 |
Preparing Stock Solutions for Chloroquine diphosphate
The following data is based on the product molecular weight 515.86. 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 | 1.94 mL | 9.69 mL | 19.39 mL |
| 5 mM | 0.39 mL | 1.94 mL | 3.88 mL |
| 10 mM | 0.19 mL | 0.97 mL | 1.94 mL |
| 50 mM | 0.04 mL | 0.19 mL | 0.39 mL |
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Product Datasheets for Chloroquine diphosphate
References for Chloroquine diphosphate
References are publications that support the biological activity of the product.
Jiang et al (2010) Antitumor and antimetastatic activities of chloroquine diphosphate in a murine model of breast cancer. Biomed.Pharmacother. 64 609 PMID: 20888174
Sasaki et al (2010) Chloroquine potentiates the anti-cancer effect of 5-fluorouracil on colon cancer cells. BMC Cancer 10 370 PMID: 20630104
Wang et al (2020) Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro. Cell Research 30
Tietze et al (1980) Chloroquine and ammonium ion inhibit receptor-mediated endocytosis of mannose-glycoconjugates by macrophages: Apparent inhibition of receptor recycling. Biochem.Biophys.Res.Commun. 93 1 PMID: 7378072
Chandler et al (2019) Enhancement of adeno-associated cirus-mediated gene therapy using hydroxychloroquine in murine and human tissues. Mol.Ther.Methods Clin.Dev. 14 77 PMID: 31309129
McErlean et al (2021) Rational design and characterisation of a linear cell penetrating peptide for non-viral gene delivery. J.Control.Release 330 1288 PMID: 33227336
If you know of a relevant reference for Chloroquine diphosphate, please let us know.
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13 Citations for Chloroquine diphosphate
Citations are publications that use Tocris products. Selected citations for Chloroquine diphosphate include:
Stephan et al (2022) Imatinib disturbs lysosomal function and morphology and impairs the activity of mTORC1 in human hepatocyte cell lines. Food Chem Toxicol 162 112869 PMID: 35182693
Markus D et al (2022) A systemic cell stress signal confers neuronal resilience toward oxidative stress in a Hedgehog-dependent manner. Cell Rep 41 111488 PMID: 36260999
Julien et al (2022) Thrombolysis by PLAT/tPA increases serum free IGF1 leading to a decrease of deleterious autophagy following brain ischemia. Autophagy 18 1297-1317 PMID: 34520334
Gupta et al (2014) Opioid receptor function is regulated by post-endocytic peptide processing. J Biol Chem 289 19613 PMID: 24847082
Lisa D et al (2023) A Ubiquitination Cascade Regulating the Integrated Stress Response and Survival in Carcinomas. Cancer Discov 13 766-795 PMID: 36576405
Tong et al (2018) Corilagin inhibits breast cancer growth via reactive oxygen species-dependent apoptosis and autophagy. J Cell Mol Med PMID: 29923307
Nariman et al (2021) Conserved residues in the extracellular loop 2 regulate Stachel-mediated activation of ADGRG2. Sci Rep 11 14060 PMID: 34234254
Jeroen et al (2021) Pancreatic beta cell autophagy is impaired in type 1 diabetes. Diabetologia 64 865-877 PMID: 33515072
Jing et al (2021) Metformin Inhibits the Urea Cycle and Reduces Putrescine Generation in Colorectal Cancer Cell Lines. Molecules 26 PMID: 33915902
George et al (2021) Endothelial Tpl2 regulates vascular barrier function via JNK-mediated degradation of claudin-5 promoting neuroinflammation or tumor metastasis. Cell Rep 35 109168 PMID: 34038728
Young Ho et al (2021) Pathogenic GRM7 Mutations Associated with Neurodevelopmental Disorders Impair Axon Outgrowth and Presynaptic Terminal Development. J Neurosci 41 2344-2359 PMID: 33500274
Thomas C et al (2021) Alphaherpesvirus-induced activation of plasmacytoid dendritic cells depends on the viral glycoprotein gD and is inhibited by non-infectious light particles. PLoS Pathog 17 e1010117 PMID: 34843605
Mark et al (2017) High Concentrations of Rosiglitazone Reduce mRNA and Protein Levels of LRP1 in HepG2 Cells. Front Pharmacol 8 772 PMID: 29201005
Do you know of a great paper that uses Chloroquine diphosphate from Tocris? Please let us know.
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