What is Chloroquine diphosphate?

Properties

Chemical name: N4-(7-Chloro-4-quinolinyl)-N1,N1-dimethyl-1,4-pentanediamine diphosphate salt

Molecular Weight: 515.86

Chemical structure:    

Molecular Formula: C18H26ClN3?2H3PO4

CAS Number: 50-63-5

PubChem identifier: 64927

SMILES: CCN(CC)CCCC(C)NC2=CC=NC1=CC(Cl)=CC=C12.O=P(O)(O)O.O=P(O)(O)O

InChi: 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)

InChiKey: QKICWELGRMTQCR-UHFFFAOYSA-N

MDL number: MFCD00069852

Chloroquine diphosphate is a derivative of 4-aminoquinoline, which is an inhibitor of autophagy and has antimalarial and anticancer activities.1-3) In addition, chloroquine has been also reported to exert anti-corona viral activity in vitro.4) The mechanism of action of chloroquine is not completely understood. But, some studies have demonstrated that chloroquine is a weak base and may exert its effect by concentrating in the acid vesicles of the parasite and by inhibiting polymerization of heme. In addition, while chloroquine can inhibit certain enzymes, its effect is believed to result, at least in part from its interaction with DNA. (The product is for research purpose only.)

Biological activity

Chloroquine diphosphate 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).

In Vitro

Chloroquine diphosphate Inhibits tumor cell growth and metastasis and induces apoptosis in vitro. Binds to Fe(II)-protoporphyrin IX (FP) to form FP-chloroquine complex resulting in cell lysis and parasite cell autodigestion.

Antimalarial compound with various biological actions (anti-inflammatory, immunomodulatory, antiviral, anticancer etc.). It inhibits cell growth, proliferation and viability and also induces apoptosis and autophagy. It inhibits viral replication to show antiviral activity and inhibits SARS-CoV-2 viral infection (COVID-19) in vitro.