Research Article. The Influence of Some Parameters on Chiral Separation of Ibuprofen by High-Performance Liquid Chromatography and Capillary Electrophoresis

Open access


Objective: The aim of the study was to compare the influence of mobile phase composition and temperature on chiral separation of racemic ibuprofen by capillary electrophoresis and high performance liquid chromatography with UV detection. Materials and methods: Racemic ibuprofen was analysed on a chiral OVM column with an HPLC system 1100 Agilent Technologies, under isocratic elution, by using potassium dihydrogen phosphate 20 mM and ethanol in mobile phase. The flow rate was set at 1 mL/min, UV detector at 220 nm and different column temperatures were tested. For electrophoresis separation an Agilent CE G1600AX Capillary Electrophoresis System system, with UV detection, was used. The electrophoresis analysis was performed at different pH values and temperatures, with phosphate buffer 25 mM and methyl-β-cyclodextrin as chiral selector. Results: The chromatograhic analysis reveals a high influence of mobile phase pH on ibuprofen enantiomers separation. An elution with a mixture of potassium dihydrogen phosphate 20 mM pH=3 and ethanol, at 25°C, allowed enantiomers separation with good resolution in less than 8 min. Conclusions: The proposed HPLC method proved suitable for the separation of ibuprofen enantiomers with a good resolution, but the capillary electrophoresis tested parameters did not allow chiral discrimination.

1. Kjonaas RA, Williams PE, Counce DA, Crawley LR. Synthesis of Ibuprofen in the Introductory Organic Laboratory. J Chem Educ. 2011;88:825-828.

2. Schurig V. The Importance of Chirality in Nature and Methods of the Separation of Enantiomers by Chiral Chromatography. Arab J Chem. 2008;1:111-122.

3. El-Fatatry HM, Mabrouk MM, Hammad SF, El-Malla SF. A Validated Enantioselective HPLC Method for Determination of Ibuprofen Enantiomers in Bulk and Tablet Dosage Form. J AOAC Int, 2016;99:604-611.

4. Loudiki A, Boumya W, Hammani H, Nasrellah H, El Bouabi Y, Zeroual M, Farahi A, Lahrich S, Hnini K, Achak M, Bakasse M, El Mhammedi MA. Ibuprofen-analysis in blood samples by palladium particles-impregnated sodium montmorillonite electrodes: Validation using high performance liquid chromatography. Mater Sci Eng C Mater Biol Appl. 2016; 69:616-624.

5. Rong L, Liu Q, Wang J, Zeng H, Yang H, Chen X. Enantioseparation of (RS)-ibuprofen by closed recycling high-speed counter-current chromatography using hydroxypropyl-beta-cyclodextrin as chiral selector. Tetrahedron-Asymmetry. 2016;27:301-306.

6. Nakov N, Petkovska R, Ugrinova L, Kavrakovski Z, Dimitrovska A, Svinarov D. Critical development by design of a rugged HPLC-MS/MS method for direct determination of ibuprofen enantiomers in human plasma. J Chromatogr B - Anal Technol Biomed Life Sci. 2015;992:67-75.

7. Zhang L, Yu W, Rong Y, Guo X, Ye J, Shena Z, Zeng S. Enantiomeric separation of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs and beta-blockers by RP-HPLC using an amylose chiral stationary phase for the enantioselective skin permeation study. Anal Method. 2014;6:6058-6065.

8. Ali I, Hussain I, Saleem K, Aboul-Enein HY. Enantiomeric Resolution of Ibuprofen and Flurbiprofen in Human Plasma by SPE-Chiral HPLC Methods. Comb Chem High Throughput Screen. 2012;15:509-514.

9. Johannsen M. Separation of enantiomers of ibuprofen on chiral stationary phases by packed column supercritical fluid chromatography. J Chromatogr A. 2011;937:135-138.

10. Crețu G, Ionică M, Dănet AF, Aboul-Enein H, Macavei R, Buleandră M. Separation of the enantiomers of ibuprofen by a gaz chromatographic - mass spectrofophotometric method. Acta Chromatographica. 2005;15:315-321.

11. Hashim NH, Khan SJ. Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples. J Chromatogr A. 2011;1218:4746-4754.

12. Hamoudova R, Pospisilova M. Determination of ibuprofen and flurbiprofen in pharmaceuticals by capillary zone electrophoresis. J Pharm Biomed Anal. 2006;41:1463-1467.

13. Juvancz Z, Bodáné-Kendrovics R, Iványi R, Szente L. The role of cyclodextrins in chiral capillary electrophoresis. Electrophoresis. 2008;29:1701-1712.

14. Kawai T, Koino H, Sueyoshi K, Kitagawa F, Otsuka K. Highly sensitive chiral analysis in capillary electrophoresis with large-volume sample stacking with an electroosmotic flow pump. J Chromatogr A. 2012;1246:28-34.

15. Prokhorova AF, Larin VA, Mikhalyuk AN, Staroverov SM, Shapovalova EN, Shpigun OA. Enantioseparation of organic acids of pharmaceutical interest using eremomycin as a chiral selector. Electrophoresis. 2011;32(SI19):2663-2668.

16. Glowka F, Karazniewicz M. Enantioselective CE method for pharmacokinetic studies on ibuprofen and its chiral metabolites with reference to genetic polymorphism. Electrophoresis. 2007;28:2726-2737.

17. Imre S, Ormenişan A, Muntean DL, Tero-Vescan A, Vari CE. HPLC Enantioseparation of Beta-Blockers on Ovomucoid Stationary Phase. J Chromatogr Sci. 2016;54:1578-1583.

18. Cârje A, Ion V, Muntean DL, Hancu G, Balint A, Imre S. Enantioseparation of indapamide by high performance liquid chromatography using ovomucoid glycoprotein as chiral selector. Farmacia. 2016;64:181-186.

19. Awad H, Aboul-Enein HY, Lashin S. A validated enantioselective HPLC assay of dexibuprofen in dexibuprofen tablet formulations. Biomed Chromatogr. 2012;26:502-506.

20. Mehlisch DR, Sykes J. Ibuprofen blood plasma levels and onset of analgesia. Int J Clin Pract Suppl. 2013;178:3-8.

Acta Medica Marisiensis

The Journal of The University of Medicine and Pharmacy of Targu-Mures

Journal Information


All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 140 140 29
PDF Downloads 70 70 36