The Effect of the Stationary Phase on Resolution in the HPLC-Based Separation of Racemic Mixtures Using Vancomycin as a Chiral Selector: A Case Study with Profen Nonsteroidal Anti-Inflammatory Drugs

Author:

Gherdaoui Dehbiya1,Yahoum Madiha Melha23,Toumi Selma3,Tahraoui Hichem45,Bouazza Fatma16,Lefnaoui Sonia13,Zeghdaoui Abdelhamid7,Amrane Abdeltif8ORCID,Jaouadi Bassem9,Zhang Jie10ORCID

Affiliation:

1. Laboratory of Experimental Biology and Pharmacology (LBPE), University of Medea, Nouveau Pole Urbain, Medea 26000, Algeria

2. Materials and Environmental Laboratory (LME), University of Medea, Nouveau Pole Urbain, Medea 26000, Algeria

3. Faculty of Sciences, University of Medea, Nouveau Pole Urbain, Medea 26000, Algeria

4. Laboratoire de Génie des Procédés Chimiques, Department of Process Engineering, University of Ferhat Abbas, Setif 19000, Algeria

5. Laboratory of Biomaterials and Transport Phenomena (LBMTP), University Yahia Fares, Medea 26000, Algeria

6. Ecole Normale Supérieure, Laboratory of Research on Bio-Active Products and Valorization of Biomasse, Vieux-Kouba, Algiers 16050, Algeria

7. Physics Department, Laboratoire N-Corps et Structure de la Matière, Ecole Normale Supérieure, B.P. 92, Vieux-Kouba, Algiers 16050, Algeria

8. Univ Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR—UMR 6226, 35000 Rennes, France

9. Laboratoire de Biotechnologie Microbienne, Enzymatique et de Biomolécules (LBMEB), Centre de Biotechnologie de Sfax (CBS), Université de Sfax, Sfax 3018, Tunisia

10. School of Engineering, Merz Court, Newcastle University, Newcastle upon Tyne NE1 7RU, UK

Abstract

Chiral resolution is a technique of choice, making it possible to obtain asymmetric and enantiomerically pure compounds from a racemic mixture. This study investigated the behavior of vancomycin when used as a chiral additive in high-performance liquid chromatography (HPLC) to separate enantiomers of nonsteroidal anti-inflammatory drugs (NSAIDs), including ketoprofen, ibuprofen, flurbiprofen, and naproxen enantiomeric impurities. We compared two achiral stationary phases (C18 and NH2) to assess the impact of mobile phase composition and stationary phase on the vancomycin retention time in the racemic resolution of drug enantiomers. Our results demonstrated the successful enantioseparation of all drugs using vancomycin in the mobile phase (phosphate buffer 0.05 M/2-propanol, 50/50) with an NH2 column. This enhanced separation on the NH2 column resulted from the chromatography system’s efficiency and vancomycin dimers’ stereoselective interaction on the NH2 surface. This study underscores the importance of stationary phase selection in the chiral resolution of NSAIDs with vancomycin as a chiral additive. It offers valuable insights for future research and development of NSAID chiral separation methods, highlighting potential vancomycin applications in this context.

Publisher

MDPI AG

Subject

Physics and Astronomy (miscellaneous),General Mathematics,Chemistry (miscellaneous),Computer Science (miscellaneous)

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