| Synonyms |
N4-(7-Chloro-4-quinolinyl)-N1,N1-dimethyl-1,4-pentanediamine diphosphate salt; Aralen diphosphate; C2301; C 2301; C-2301; Chloroquine Diphosphate |
| IUPAC Name |
4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine;phosphoric acid |
| Molecular Weight |
515.86 |
| Molecular Formula |
C18H32ClN3O8P2 |
| Canonical SMILES |
CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl.OP(=O)(O)O.OP(=O)(O)O |
| 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 |
| Boiling Point |
460.6ºC at 760 mmHg |
| Melting Point |
199°C(dec.)(lit.) |
| Flash Point |
232.3ºC |
| Purity |
≥98% (HPLC) |
| Solubility |
Water: 30mg/mL |
| Appearance |
White solid |
| Application |
Anti-Inflammatory Agents, Non-Steroidal |
| Storage |
Desiccate at RT |
| Animal Admin |
Treatments are started seven days after tumor cell inoculation. The mice are treated daily either with intraperitoneal (i.p.) chloroquine (80 mg/kg) or vehicle (PBS). Tumor measurements are performed twice a week and tumor volume is calculated according to the formula V=(π/6) (d1×d2)3/2, where d1 and d2 are perpendicular tumor diameters. Throughout the experiments, the animals are maintained under controlled pathogen-free environmental conditions (20-21°C, 30-60% relative humidity and a 12-h lighting cycle). The mice are fed with small-animal food pellets and supplied with sterile water ad libitum. |
| Assay |
The cells are cultured in 6-well plates with normal culture medium in the presence of vehicle or 25 or 50 μM chloroquine, until near confluency, after which they are rinsed with sterile phosphate-buffered saline (PBS) and cultured further for the indicated times in serum-free culture medium. Secondary detection is performed with horseradish peroxidase-linked secondary antibodies. The protein bands are visualized by chemiluminescence using an ECL kit. |
| Complexity |
359 |
| Exact Mass |
515.1353167 |
| In Vitro |
Chloroquine (CHQ, 20 μM) inhibits IL-12p70 release and reduces Th1-priming capacity of activated human monocyte-derived Langerhans-like cells (MoLC). Chloroquine (20 μM) enhances IL-1-induced IL-23 secretion in MoLC and subsequently increases IL-17A release by primed CD4+ T cells. Chloroquine (25 μM) suppresses MMP-9 mRNA expression in normoxia and hypoxia in parental MDA-MB-231 cells. TLR7 and TLR9 inhibition using IRS-954 or chloroquine significantly reduces HuH7 cell proliferation in vitro. Chloroquine (0.01-100μM; 48 hours) potently blocked virus infection (vero E6 cells infected with SARS-CoV-2) at low-micromolar concentration (EC50=1.13 μM). Chloroquine 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 (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 significantly inhibits tumour growth in the mouse xenograft model. HCC development in the DEN/NMOR rat model is also significantly inhibited by Chloroquine. |
| PSA |
23.3 |
| Target |
Autophagy, TLRs |
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