HPLC Enantioseparation of β-Blockers on Ovomucoid Stationary Phase

Abstract

The purpose of this study was to separate single and multiple pairs of six β-blockers enantiomers by high performance liquid chromatography on ovomucoid (OM) column in optimal conditions. The separation was performed isocratically or in gradient elution at 25°C, flow rate of 1 mL/min and 220 nm. The mobile phase consisted of phosphate buffer/acetonitrile or methanol. The effect of the organic modifier, the influence of pH and the percentage of the aqueous phase on resolution were investigated. The elution order of propranolol (PRP) enantiomers was established as well as the detection and quantification limits. The results show that OM was suitable for enantiomeric separation of the nonselective β-blockers carvedilol, PRP, pindolol and oxprenolol, and not for the two β-1 selective blockers, atenolol and metoprolol. A hypothesis regarding a possible correlation between structure-pharmacological activity-chromatographic behavior is proposed.

Bioassay, determination and separation of enantiomers of atenolol by direct and indirect approaches using liquid chromatography: A review

“…Imre, Ormenişan, Tero‐Vescan, Muntean, and Vari () carried out resolution studies on single and multiple pairs of enantiomers of six β ‐adrenolytics, including Atl, by HPLC on ovomucoid column using both isocratic and gradient elution modes at a flow rate of 1 mL min −1 and 220 nm. The mobile phase consisted of phosphate buffer–acetonitrile or methanol and the effects of change of organic modifier, pH and the percentage of the aqueous phase on resolution were investigated.…”

“…Peak I, (R)-amlodipine; peak II, (S)-amlodipine; peak III, (R)-Atl; peak IV, (S)-Atl enantiomeric separation of the nonselective β-adrenolytics (carvedilol, propranolol, pindolol and oxprenolol) and not for the β 1 selective blocker, Atl (and metoprolol). It was suggested that the presence of two p-oriented polar substituents on the benzene ring in Atl molecule is probably an unfavorable structural factor for resolution on this type of CSP (Imre et al, 2016).…”

Methods and approaches for determination and enantioseparation of (RS)‐propranolol

“…The ovomucoid column, in HPLC, was successful for resolving single and multiple pairs of enantiomers of six β ‐adrenolytics, including Prl (Imre, Ormenişan, Tero‐Vescan, Muntean &Vari, ), under both isocratic and gradient elution modes at a flow rate of 1 mL min −1 and 220 nm. The column was suitable for enantiomeric resolution of the nonselective β ‐adrenolytics,e.g., Prl (and also, carvedilol pindolol and oxprenolol), and not for the β 1 selective adrenolytics,i.e., atenolol and metoprolol.…”

A chiral magnetic molybdenum disulfide nanocomposite for direct enantioseparation of RS-propranolol

“…4,5 b-Adrenergic blocking agents (b-blockers), as a type of representative chiral drugs, are widely used for the treatment of angina, cardiac arrhythmias, hypertension, myocardial infarction and glaucoma. [6][7][8][9] They are commonly marketed and administered as racemic mixtures. The pharmacological activities usually reside in the S-enantiomer owing to its higher stereoselective affinity toward b-receptors, while the R-enantiomer is pharmacologically inactive or even toxic in some cases.…”