C6628

Chloroquine diphosphate salt

98.5-101.0% (EP), powder or crystals, autophagy inhibitor

• Synonym(s): N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine diphosphate, N⁴-(7-Chloro-4-quinolinyl)-N¹,N¹-dimethyl-1,4-pentanediamine diphosphate salt
• Empirical Formula (Hill Notation): C₁₈H₂₆ClN₃ · 2H₃PO₄
• CAS Number: 50-63-5
• Molecular Weight: 515.86
• Beilstein: 4223142
• EC Number: 200-055-2
• MDL number: MFCD00069852
• UNSPSC Code: 12352107
• PubChem Substance ID: 24278090
• NACRES: NA.77

Properties

• Product Name: Chloroquine diphosphate salt, powder or crystals, 98.5-101.0% (EP)
• Quality Level: 200
• Assay: 98.5-101.0% (EP)
• form: powder or crystals
• mp: 192-198 °C
• antibiotic activity spectrum: parasites
• Mode of action: enzyme | inhibits
• SMILES string: OP(O)(O)=O.OP(O)(O)=O.CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12
• InChI: 1S/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;2*1-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*(H3,1,2,3,4)
• InChI key: QKICWELGRMTQCR-UHFFFAOYSA-N
• Gene Information: human ... ABCC1(4363)

Description

General description

Chloroquine effectively eliminates the erythrocytic forms of malaria parasites at all developmental stages, although it does not impact the sporozoites. It also functions as an antibiotic. In addition, it can be utilized at a concentration of 200 mg/mL (PBS, pH 5.0) to dissociate antigen-antibody complexes without denaturing red blood cell antigens. Recent research indicates chloroquine′s potential as an antitumor medication for cancer treatment along with chemotherapy and radiation. Its antimalarial effects are achieved by inhibiting the polymerization of heme into hemozoin, which serves as a food source for the malarial parasite. Chloroquine forms a complex with the drug-hemozoin, capping the polymerizing chain and preventing further polymerization. As a result, free heme accumulates in the food vacuole, exerting toxic effects on the parasite. Additionally, chloroquine acts as an anti-autoimmune therapy by binding to transcriptional factors on T helper 17 cells and inhibiting their differentiation.[1] Chloroquine diphosphate (CQ) is frequently employed as an inhibitor of the autophagic pathway. The combined use of chloroquine diphosphate and salidroside initiates apoptosis in human liver cells by modulating mitochondrial dysfunction and autophagy.[2]

Chloroquine is a member of quinolone family[3] and is a weak intercalating agent.[4] Chloroquine is used for treating amebiasis, rheumatoid arthritis, discoid and systemic lupus erythematosus.[5]

Application

DNA intercalator. Also used to increase transfection efficiency.
Chloroquine diphosphate salt has been used :

• in in vitro antiplasmodial assays[6]
• in transfection and infection assays[7]
• in autophagy inhibition[8]
• in differentiation of induced pluripotent stem (iPS) cells into cardiomyocytes[9]
• in flow treatment of infected blood[10]

Biochem/physiol Actions

Standard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labeling of MRP by quinoline-based photoactive drug IAAQ (N-[4-[1-hydroxy-2-(dibutylamino)ethyl]quinolin-8-yl]-4-azidosalicylamide).

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves