Electronic Circular Dichroism Spectroscopy

Zsila, Ferenc

doi:10.1002/9780470571224.pse405

Cited by 6 publications

(9 citation statements)

References 295 publications

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“…An alternative approach is to use currently validated HPLC assay methods to separate the substance of interest from other components and apply chiral-specific detectors such as circular dichroism (CD) or optical rotation to verify that the correct enantiomer is present and meets the minimum enantiomeric purity criteria. [2] A series of articles have explored the potential for this approach, [3–16] but these studies have not focused on compatibility with methods validated by the US Pharmacopeia (USP).…”

Section: Introductionmentioning

confidence: 99%

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Determination of the enantiomeric purity of epinephrine by HPLC with circular dichroism detection

Kirkpatrick

Yang

Trehy

2017

Journal of Liquid Chromatography & Related Technologies

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Several hundred drug substances approved by the U.S. Food and Drug Administration are chiral molecules. For the enantiomeric purity assessment, current practice is to develop separation techniques using chiral columns or mobile phase modifiers to separate enantiomers before detection. An alternative approach is to use currently accepted HPLC assay methods and use chiral-specific detectors to confirm whether the correct enantiomer is present. In this paper, adding a circular dichroism (CD) detector to an achiral HPLC method from the US Pharmacopeia (USP) is shown to be amenable for the determination of the enantiomeric purity of epinephrine, a substance used to treat anaphylaxis. This HPLC-UV-CD approach was able to detect the inactive D-(+) enantiomer at 1% of the total epinephrine composition. The linearity, accuracy, and precision of HPLC-UV-CD were evaluated and compared to analyses using a chiral HPLC method. Additionally, an epinephrine drug product was analyzed for assay (concentration) and enantiomeric purity. The results from achiral and chiral methods were identical within the experimental error. Overall, achiral chromatography performed using a USP method with CD detection may serve as a general means of determining chiral drug enantiomer purity and avoids the need for the development of additional chiral-specific methods for each individual drug.

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Section: Introductionmentioning

confidence: 99%

“…This value is called the g-factor

(g = 1 \frac{Δ A}{A})

and can be used to determine the enantiomeric purity of a chiral substance. [2] …”

Section: Introductionmentioning

confidence: 99%

Determination of the enantiomeric purity of epinephrine by HPLC with circular dichroism detection

Kirkpatrick

Yang

Trehy

2017

Journal of Liquid Chromatography & Related Technologies

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“…The main purpose of this work is to show that ECD can be used as a tool to determine enantiopurity of pharmaceuticals [ 22 ] when more sophisticated methods are not readily available, such as the ones discussed in the literature [ 23 – 25 ]. One advantage of ECD is that it can rapidly discriminate enantiomers, as well as diastereomers, and has the ability to determine the composition of racemic mixtures [ 26 ]. ECD requires millimolar or lesser concentrations, making it well-suited for use when the quantity of the sample is limited.…”

Section: Introductionmentioning

confidence: 99%

Applied Circular Dichroism: A Facile Spectroscopic Tool for Configurational Assignment and Determination of Enantiopurity

Okuom

Burks

Naylor

et al. 2015

Journal of Analytical Methods in Chemistry

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In order to determine if electronic circular dichroism (ECD) is a good tool for the qualitative evaluation of absolute configuration and enantiopurity in the absence of chiral high performance liquid chromatography (HPLC), ECD studies were performed on several prescriptions and over-the-counter drugs. Cotton effects (CE) were observed for both S and R isomers between 200 and 300 nm. For the drugs examined in this study, the S isomers showed a negative CE, while the R isomers displayed a positive CE. The ECD spectra of both enantiomers were nearly mirror images, with the amplitude proportional to the enantiopurity. Plotting the differential extinction coefficient (Δε) versus enantiopurity at the wavelength of maximum amplitude yielded linear standard curves with coefficients of determination (R 2) greater than 97% for both isomers in all cases. As expected, Equate, Advil, and Motrin, each containing a racemic mixture of ibuprofen, yielded no chiroptical signal. ECD spectra of Suphedrine and Sudafed revealed that each of them is rich in 1S,2S-pseudoephedrine, while the analysis of Equate vapor inhaler is rich in R-methamphetamine.

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“…When a drug binds to a protein molecule the molar ellipticity change ∆ θ is obtained at wavelengths where the drug has absorption bands and ∆ θ is proportional to the concentration of drug-protein complexes (D t ∪ P T ), where P T is the total protein concentration and D t is the total drug concentration [2][3][4][5].…”

mentioning

confidence: 99%

“…The proposed method in [ 1 ] is used for analyzing data for drug protein binding in several publications [ 2,3,[6][7][8][9][10] ].…”

mentioning

confidence: 99%

Statistical Properties of the Least Square Estimators for Drug-protein Binding

Prodanova¹

2013

Proceeding BAS

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Electronic Circular Dichroism Spectroscopy

Cited by 6 publications

References 295 publications

Determination of the enantiomeric purity of epinephrine by HPLC with circular dichroism detection

Determination of the enantiomeric purity of epinephrine by HPLC with circular dichroism detection

Applied Circular Dichroism: A Facile Spectroscopic Tool for Configurational Assignment and Determination of Enantiopurity

Statistical Properties of the Least Square Estimators for Drug-protein Binding

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