C6628

Sigma-Aldrich

Chloroquine diphosphate salt

powder or crystals, 98.5-101.0% (EP)

Sinónimos:
N4-(7-Chloro-4-quinolinyl)-N1,N1-dimethyl-1,4-pentanediamine diphosphate salt, N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine diphosphate
Empirical Formula (Hill Notation):
C18H26ClN3 · 2H3PO4
Número de CAS:
Peso molecular:
515.86
Beilstein/REAXYS Number:
4223142
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

98.5-101.0% (EP)

form

powder or crystals

mp

193-198 °C
200 °C (dec.) (lit.)

Mode of action

enzyme | inhibits

antibiotic activity spectrum

parasites

SMILES string

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)

InChI key

QKICWELGRMTQCR-UHFFFAOYSA-N

Gene Information

human ... ABCC1(4363)

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General description

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.

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

Packaging

25, 50, 100, 250 g in glass bottle

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

pictograms

Exclamation mark

signalword

Warning

hcodes

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

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)
Malaria theranostics using hemozoin-generated vapor nanobubbles
Lukianova-Hleb EY and Lapotko DO
Theranostics, 4(7), 761-761 (2014)
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)
Ecotoxicological evaluation of the antimalarial drug chloroquine
Zurita JL, et al.
Aquatic Toxicology (Amsterdam, Netherlands), 75(2), 97-107 (2005)
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)
Artículos
We presents an article on Autophagy in Cancer Promotes Therapeutic Resistance
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Protein-based drug transporters are found in most tissues including liver, kidney, intestine, and brain. These transporters are particularly important in cancer treatment and multi-drug resistance research. Understanding the specific mechanisms of tumor cell transporters is becoming an essential aspect of chemotherapeutic drug design.
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