C6628

Chloroquine diphosphate salt

Name: Chloroquine diphosphate salt
Brand: SIGMA

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

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₂₆ClN₃ · 2H₃PO₄

CAS Number:

50-63-5

Molecular Weight:

515.86

NACRES:

NA.77

PubChem Substance ID:

24278090

UNSPSC Code:

12352107

EC Number:

200-055-2

MDL number:

MFCD00069852

Beilstein/REAXYS Number:

4223142

Product Name

Chloroquine diphosphate salt, powder or crystals, 98.5-101.0% (EP)

InChI key

QKICWELGRMTQCR-UHFFFAOYSA-N

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 string

OP(O)(O)=O.OP(O)(O)=O.CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12

assay

98.5-101.0% (EP)

form

powder or crystals

mp

192-198 °C

antibiotic activity spectrum

parasites

mode of action

enzyme | inhibits

Quality Level

200

Gene Information

human ... ABCC1(4363)

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Phosphates

Application

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

in in vitro antiplasmodial assays
in transfection and infection assays
in autophagy inhibition
in differentiation of induced pluripotent stem (iPS) cells into cardiomyocytes
in flow treatment of infected blood

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.

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. 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.

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

Other Notes

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

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000479042

0000439771

0000424164

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Pompe disease results in a Golgi-based glycosylation deficit in human induced pluripotent stem cell-derived cardiomyocytes

Raval KK, et al.

The Journal of Biological Chemistry, 290(5), 3121-3136 (2015)

Combination of chloroquine diphosphate and salidroside induces human liver cell apoptosis via regulation of mitochondrial dysfunction and autophagy

Bing J, et al.

Molecular Medicine Reports, 27, 1-12 (2023)

Malaria theranostics using hemozoin-generated vapor nanobubbles

Lukianova-Hleb EY and Lapotko DO

Theranostics, 4(7), 761-761 (2014)

E2F1 modulates p38 MAPK phosphorylation via transcriptional regulation of ASK1 and Wip1

Hershko T, et al.

The Journal of Biological Chemistry, 281(42), 31309-31316 (2006)

Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity

Jonville MC, et al.

Journal of Ethnopharmacology, 120(3), 382-386 (2008)

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