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    Chloroquine Phosphate
    Chloroquine Phosphate

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V2530
    CAS #: 50-63-5Purity ≥98%

    Description: Chloroquine phosphate is reported to be highly effective in combating SARS-CoV-2 (COVID-19, CoronaVirus, or the COVID-19 pandemic) infection in vitro. It acts as a potent autophagy and toll-like receptors (TLRs) inhibitor, and a 4-aminoquinoline anti-malarial medication used to prevent and to treat malaria in areas where malaria is known to be sensitive to its effects. It is also an anti-rheumatoid agent, also acting as an ATM activator. Chloroquine diphosphate has been reported as an adjuvant for radiation and chemotherapy for inducing cell autophagy to anti-cancer cells proliferation or metastasis. The mechanism of chloroquine diphosphate inducing cells autophagy is arresting cells in G1, up-regulates the expression of p27 and p53 while down-regulates the expression of CDK2 and cyclin D1.

    References: Lancet Infect Dis. 2003 Nov;3(11):722-7; Curr Opin Microbiol. 2000 Aug;3(4):349-53.

    Related CAS#: 54-05-7 (free base); 132-73-0 (sulfate); 1446-17-9 (phosphate); 3545-67-3 (HCl); 50-63-5 (diphosphate); 4298-14-0 (Didesethyl chloroquine); 1476-52-4 (Desethyl chloroquine); 247912-76-1 (Desethyl chloroquine diphosphate)

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    Molecular Weight (MW)515.86
    CAS No.50-63-5  (diphosphate); 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: <1 mg/mL
    Water: 100 mg/mL (193.9 mM)
    Ethanol: <1 mg/mL
    Other info
    Chemical Name: N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine bis(phosphate)
    InChi Code: 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)
    SMILES Code: CC(NC1=CC=NC2=CC(Cl)=CC=C12)CCCN(CC)CC.O=P(O)(O)O.O=P(O)(O)O 
    SynonymsChloroquine diphosphate; Chingamin, Miniquine, Resochin, Chloroquine, Aralen, Arechin, Tanakan 

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    In Vitro

    In vitro activity: Chloroquine is a chemotherapeutic agent for the clinical treatment of malaria. Chloroquine is able to bind to DNA, and inhibit DNA replication and RNA synthesis which in turn results in cell death. The effect of Chloroquine may also be related to the formation of a toxic heme-Chloroquine complex. Chloroquine inhibits trophozoite hemoglobin degradation through increasing vacuolar pH and inhibiting the activity of vacuolar phospholipase, vacuolar proteases, and heme polymerase. Chloroquine possesses definite antirheumatic properties. Chloroquine has immuno-modulatory effects, suppressing the production/release of tumour necrosis factor and interleukin 6. Moreover, Chloroquine exerts direct antiviral effects, inhibiting pH-dependent steps of the replication of several viruses including members of the flaviviruses, retroviruses, and coronaviruses. Its best-studied effects are those against HIV replication. Chloroquine can accumulate inside the macrophage phagolysosome by ion trapping where it exerts potent antifungal activity against Histoplasma capsulatum and Cryptococcus neoformans by distinct mechanisms. Chloroquine inhibits growth of H. capsulatum by pH-dependent iron deprivation, whereas it is directly toxic to C. neoformans.

    Cell 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. At the desired time-points, the culture medium is discarded and the cells are quickly harvested in lysis buffer and clarified by centrifugation. Subsequent to boiling the supernatants in reducing sodium dodecyl sulphate (SDS) sample buffer, equal amounts of protein (100 μg) are loaded per lane and the samples are electrophoresed into 10 or 4-20% gradient polyacrylamide SDS gels, then transferred to a nitrocellulose membrane. To detect TLR9, the blots are incubated overnight at 4°C with anti-TLR9 antibodies, diluted 1:500 in Tris-buffered saline with 0.1% (v/v) Tween-20 (TBST). Equal loading is confirmed with polyclonal rabbit anti-actin. Secondary detection is performed with horseradish peroxidase-linked secondary antibodies. The protein bands are visualized by chemiluminescence using an ECL kit.

    In VivoChloroquine (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. In mouse model with 4T1 cells subcutaneous xenograft, chloroquine diphosphate treatment significantly inhibited tumor growth and tumor cells metastasis to the lung, thus enhanced the mice survival. In BALB/c mice injected with colon26 cells subcutaneously, chloroquine diphosphate cooperated with 5-FU significantly enhanced the inhibition of tumor growth induced by 5-FU through increasing the ratio of apoptotic cells.
    Animal modelMice: Control and TLR9 siRNA MDA-MB-231 cells (5×105 cells in 100 μL) are inoculated into the mammary fat pads of four-week-old, immune-deficient mice (athymic nude/nu Foxn1). 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). The animals are monitored daily for clinical signs. 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. The tumors are allowed to grow for 22 days, at which point the mice are sacrificed and the tumors are dissected for a final measurement. 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.
    Formulation & Dosage 80 mg/kg, i.p.
    ReferencesLancet Infect Dis. 2003 Nov;3(11):722-7; Curr Opin Microbiol. 2000 Aug;3(4):349-5; Oncol Lett. 2013 Dec;6(6):1665-1672.

    These protocols are for reference only. InvivoChem does not independently validate these methods.


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