Next Article in Journal
Synthesis of Phthalides and α,β-butenolides by Transition Metal-Catalyzed Activation of C—H Bonds
Next Article in Special Issue
Colistin Sulfate Chiral Stationary Phase for the Enantioselective Separation of Pharmaceuticals Using Organic Polymer Monolithic Capillary Chromatography
Previous Article in Journal
Analysis of 27 β-Blockers and Metabolites in Milk Powder by High Performance Liquid Chromatography Coupled to Quadrupole Orbitrap High-Resolution Mass Spectrometry
Previous Article in Special Issue
Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies
Open AccessArticle

New Brush-Type Chiral Stationary Phases for Enantioseparation of Pharmaceutical Drugs

1
Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, Zagreb 10000, Croatia
2
Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, Zagreb 10000, Croatia
3
South Ural State University, 20-A, Tchaikovsky Str., Chelyabinsk 454080, Russia
*
Author to whom correspondence should be addressed.
Academic Editors: Maria Elizabeth Tiritan, Madalena Pinto and Carla Sofia Garcia Fernandes
Molecules 2019, 24(4), 823; https://doi.org/10.3390/molecules24040823
Received: 25 January 2019 / Revised: 20 February 2019 / Accepted: 21 February 2019 / Published: 25 February 2019
The importance of chirality in drug development is unquestionable, with chiral liquid chromatography (LC) being the most adequate technique for its analysis. Among the various types of chiral stationary phases (CSPs) for LC, brush-type CSPs provide the base for interaction analysis of CSPs and enantiomers, which provide valuable results that can be applied to interaction studies of other CSP types. In order to analyze the influence of aromatic interactions in chiral recognition, we designed a set of ten new brush-type CSPs based on (S)-N-(1-aryl-propyl)-3,5-dinitrobenzamides which differ in the aromatic unit directly linked to the chiral center. Thirty diverse racemates, including several nonsteroidal anti-inflammatory drugs and 3-hydroxybenzodiazepine drugs, were used to evaluate the prepared CSPs. Chromatographic analysis showed that the three new CSPs separate enantiomers of a wide range of compounds and their chromatographic behavior is comparable to the most versatile brush-type CSP—Whelk-O1. The critical role of the nonbonding interactions in positioning of the analyte (naproxen) in the cleft of CSP-6, as well as the analysis of interactions that make enantioseparation possible, were elucidated using computational methods. Furthermore, the influence of acetic acid as a mobile phase additive, on this enantiorecognition process was corroborated by calculations. View Full-Text
Keywords: chiral chromatography; chiral recognition; intermolecular interactions; chiral drugs; Whelk-O1 column; mobile phase additives chiral chromatography; chiral recognition; intermolecular interactions; chiral drugs; Whelk-O1 column; mobile phase additives
Show Figures

Graphical abstract

MDPI and ACS Style

Knežević, A.; Novak, J.; Vinković, V. New Brush-Type Chiral Stationary Phases for Enantioseparation of Pharmaceutical Drugs. Molecules 2019, 24, 823.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop