The absolute configuration of the enantiomers of 6‐chloro‐9‐(4′‐diethylamino‐1′‐methylbutyl)‐amino‐2‐methoxyacridine (quinacrine)

Craig, J. Cymerman; LaBelle, Bruce; Ohnsorge, U.

doi:10.1002/chir.530030510

Cited by 3 publications

References 5 publications

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Electronic Circular Dichroism Spectroscopy

Zsila¹

2010

Pharmaceutical Sciences Encyclopedia

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Electronic circular dichroism (ECD or CD) is the manifestation of the important property of chiral compounds to absorb left and right circularly polarized light to different extents. Electronic circular dichroism (CD) spectroscopy technique has been used for investigation of chiral drugs and other pharmaceutical preparations. This article focuses on basic features, instrumentation, advantages, limitations, and practical applications of electronic circular dichroism (CD) spectroscopy in pharmaceutical sciences.

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Electronic Circular Dichroism Spectroscopy

Zsila¹

2010

Pharmaceutical Sciences Encyclopedia

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Differential binding of the enantiomers of chloroquine and quinacrine to polynucleotides: Implications for stereoselective metabolism

1993

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Interaction of the antimalarial drugs quinacrine and chloroquine with DNA has been studied extensively in order to understand the origin of their biological activity. These studies have shown that they bind to DNA through an intercalative mode and show little sequence specificity. All previous experiments were carried out using the racemic form of these drugs. We have investigated the binding of the enantiomeric forms of quinacrine and chloroquine to synthetic polynucleotides poly(dA-dT).poly(dA-dT) and poly(dG-dC).poly (dG-dC), and found interesting differences in their binding parameters. Quinacrine enantiomers have a much higher binding affinity for the two polynucleotides compared to those of chloroquine. The negative enantiomers were found to have higher binding affinity than the positive ones. The binding constant for the binding of quinacrine(-) to poly(dG-dC).poly(dG-dC) was found to be about 3 times that of quinacrine(+). The differences in these binding affinities were further confirmed by equilibrium dialysis of the complexes of the polynucleotides with the racemic form of the drugs, which resulted in the enrichment of the dialysate with the positive enantiomer. CD spectra of the enantiomers and their polynucleotide complexes are reported. Changes in the fluorescence properties of quinacrine in the presence of the two polynucleotides are also described. Biological implications of these findings are discussed.

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Differential Inhibition of Prion Propagation by Enantiomers of Quinacrine

Ryou

Legname

Peretz

et al. 2003

Laboratory Investigation

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SUMMARY:Prion diseases are fatal neurologic disorders caused by accumulation of a pathogenic isoform (PrP Sc ) of the prion protein (PrP). The recent discovery of the inhibitory action of quinacrine on PrP Sc formation in scrapie-infected neuroblastoma (ScN2a) cells raised the possibility of a treatment for patients with prion disease. To investigate the efficacy of quinacrine enantiomers, we measured the inhibitory effect of these isomers on PrP Sc formation in ScN2a cells. (S)-quinacrine exhibited superior antiprion activity compared with (R)-quinacrine and two generic quinacrines that appear to be racemates. Treatment with these various forms of quinacrine did not induce adverse changes affecting cell survival and the expression of marker proteins over a range of potentially therapeutic concentrations. Thus, quinacrine enantiomers demonstrated stereoselectivity on prion elimination but not cytotoxicity in ScN2a cells. Our results raise the possibility that in vivo treatment using one enantiomer of quinacrine may be superior to a racemic mixture, which is the form that is generally used when quinacrine is employed to treat parasitic diseases. (Lab Invest 2003, 83:837-843).

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The absolute configuration of the enantiomers of 6‐chloro‐9‐(4′‐diethylamino‐1′‐methylbutyl)‐amino‐2‐methoxyacridine (quinacrine)

Cited by 3 publications

References 5 publications

Electronic Circular Dichroism Spectroscopy

Electronic Circular Dichroism Spectroscopy

Differential binding of the enantiomers of chloroquine and quinacrine to polynucleotides: Implications for stereoselective metabolism

Differential Inhibition of Prion Propagation by Enantiomers of Quinacrine

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