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C6628

Sigma-Aldrich

Chloroquine diphosphate salt

98.5-101.0% (EP), powder or crystals, autophagy inhibitor

Synonyme(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

Formule empirique (notation de Hill):
C18H26ClN3 · 2H3PO4
Numéro CAS:
Poids moléculaire :
515.86
Beilstein:
4223142
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352107
ID de substance PubChem :
Nomenclature NACRES :
NA.77
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Nom du produit

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

Niveau de qualité

Essai

98.5-101.0% (EP)

Forme

powder or crystals

Pf

192-198 °C

Spectre d'activité de l'antibiotique

parasites

Mode d’action

enzyme | inhibits

Chaîne SMILES 

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

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)

Clé InChI

QKICWELGRMTQCR-UHFFFAOYSA-N

Informations sur le gène

human ... ABCC1(4363)

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Catégories apparentées

Description générale

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.[1] 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.[2]
Chloroquine is a member of quinolone family[3] and is a weak intercalating agent.[4] Chloroquine is used for treating amebiasis, rheumatoid arthritis, discoid and systemic lupus erythematosus.[5]

Application

DNA intercalator. Also used to increase transfection efficiency.
Chloroquine diphosphate salt has been used :
  • in in vitro antiplasmodial assays[6]
  • in transfection and infection assays[7]
  • in autophagy inhibition[8]
  • in differentiation of induced pluripotent stem (iPS) cells into cardiomyocytes[9]
  • in flow treatment of infected blood[10]

Actions biochimiques/physiologiques

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).

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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)
Ecotoxicological evaluation of the antimalarial drug chloroquine
Zurita JL, et al.
Aquatic Toxicology (Amsterdam, Netherlands), 75(2), 97-107 (2005)
Mechanism of inhibition of DNA gyrase by analogues of nalidixic acid: the target of the drugs is DNA
Shen LL and Pernet AG
Proceedings of the National Academy of Sciences of the USA, 82(2), 307-311 (1985)
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)

Articles

We presents an article on Autophagy in Cancer Promotes Therapeutic Resistance

Protein-based drug transporters are expressed in Sf9 cells. Understanding the specific mechanisms of tumor cell transporters is an essential aspect of chemotherapeutic drug design.

Protein-based drug transporters are expressed in Sf9 cells. Understanding the specific mechanisms of tumor cell transporters is an essential aspect of chemotherapeutic drug design.

Protein-based drug transporters are expressed in Sf9 cells. Understanding the specific mechanisms of tumor cell transporters is an essential aspect of chemotherapeutic drug design.

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Chromatograms

application for HPLC

Questions

1–3 of 3 Questions  
  1. In primary neuron culture, what concentration is used for chloroquine and what solvent is used to dissolve it?

    1 answer
    1. Per “Preparation Instructions” in the Data Sheet, Chloroquine diphosphate salt is soluble in water (50 mg/mL).
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/564/826/c6628dat-ms.pdf

      For more guidance on use in cell culture applications, we kindly ask you to navigate to the link https://www.sigmaaldrich.com/techservice, click on "Product Technical Inquires" under the Products Section with all the required information so that a member of our team can reach out to you to assist further. Thank you.

      Helpful?

  2. salve per la sua preparazione, in che soluzione si deve sciogliere ?

    1 answer
    1. This product is soluble at 50 mg/mL in water. Please see the link below to review the product datasheet:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/564/826/c6628dat-ms.pdf

      Helpful?

  3. How should I store stock solutions of this product? For how long should I store?

    1 answer
    1. Stock solutions should be protected from light and may be stored at 4 °C or in aliquots at -20 °C. The time frame for solution storage has not been determined.

      Please see the link below to review the product datasheet:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/564/826/c6628dat-ms.pdf

      Helpful?

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