Chloroquine Dihydrochloride

Category	Human immunodeficiency Virus (HIV)
CAS	3545-67-3
Description	Chloroquine diphosphateis an antimalarial and anti-inflammatory agent widely used to treat malaria and rheumatoid arthritis. Chloroquine phosphate is an Autophagy and toll-like receptors (TLRs) inhibitor. Chloroquine phosphate is highly effective in the control of SARS-CoV-2 (COVID-19) infection in vitro (EC50=1.13 μM).

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Product Information

Synonyms	1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, hydrochloride
IUPAC Name	4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine;dihydrochloride
Molecular Weight	392.79
Molecular Formula	C18H28Cl3N3
Canonical SMILES	CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl.Cl.Cl
InChI	InChI=1S/C18H26ClN3.2ClH/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;;/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*1H
InChIKey	PCFGECQRSMVKCC-UHFFFAOYSA-N
Purity	> 95%
Solubility	Insoluble in DMSO; insoluble in EtOH; ≥106.06 mg/mL in H2O
Appearance	Solid powder
Storage	Store at -20°C
Animal Admin	Chloroquine Diphosphate significantly reduced the primary tumor growth rate at 25 mg/kg and 50 mg/kg doses. In addition, 30% and 60% of mice in the 25 mg/kg and 50 mg/kg Chloroquine Diphosphate treated groups remained alive at day 61.
Assay	The MTT assay showed that Chloroquine Diphosphate inhibited 4T1 cell proliferation in a dose- and time-dependent manner.
In Vitro	Chloroquine dihydrochloride (20 μM) inhibits IL-12p70 release and reduces Th1-priming capacity of activated human monocyte-derived Langerhans-like cells (MoLC). Chloroquine dihydrochloride (20 μM) enhances IL-1-induced IL-23 secretion in MoLC and subsequently increases IL-17A release by primed CD4+T cells. Chloroquine dihydrochloride (25 μM) suppresses MMP-9 mRNA expression in normoxia and hypoxia in parental MDA-MB-231 cells. Chloroquine dihydrochloride has cell-, dose- and hypoxia-dependent effects on MMP-2, MMP-9 and MMP-13 mRNA expression. TLR7 and TLR9 inhibition using IRS-954 or Chloroquine dihydrochloride significantly reduces HuH7 cell proliferation in vitro. Chloroquine dihydrochloride (0.01-100 μM; 48 hours) potently blocked virus infection (vero E6 cells infected with SARS-CoV-2) at low-micromolar concentration (EC50=1.13 μM). Chloroquine dihydrochloride blocks virus infection by increasing endosomal pH required for virus/cell fusion, as well as interfering with the glycosylation of cellular receptors of SARS-CoV.
In Vivo	Chloroquine dihydrochloride (80 mg/kg, i.p.) does not prevent the growth of the triple-negative MDA-MB-231 cells with high or low TLR9 expression levels in the orthotopic mouse model. TLR7 and TLR9 inhibition using IRS-954 or Chloroquine dihydrochloride significantly inhibits tumour growth in the mouse xenograft model. HCC development in the DEN/NMOR rat model is also significantly inhibited by Chloroquin.
PSA	28.16000
Target	Parasite; Autophagy; SARS-CoV; Toll-like Receptor (TLR); HIV; Antibiotic