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. 2019 Feb 26;24(5):833.
doi: 10.3390/molecules24050833.

Colistin Sulfate Chiral Stationary Phase for the Enantioselective Separation of Pharmaceuticals Using Organic Polymer Monolithic Capillary Chromatography

Ali Fouad  1   2 , Montaser Sh A Shaykoon  3 , Samy M Ibrahim  4 , Sobhy M El-Adl  5 , Ashraf Ghanem  6
Affiliations

Colistin Sulfate Chiral Stationary Phase for the Enantioselective Separation of Pharmaceuticals Using Organic Polymer Monolithic Capillary Chromatography

Ali Fouad et al. Molecules. .

Abstract

A new functionalized polymer monolithic capillary with a macrocyclic antibiotic, namely colistin sulfate, as chiral selector was prepared via the copolymerization of binary monomer mixtures consisting of glycidyl methacrylate (GMA) and ethylene glycol dimethacrylate (EGDMA) in porogenic solvents namely 1-propanol and 1,4-butanediol, in the presence of azobisiso-butyronitrile (AIBN) as initiator and colistin sulfate. The prepared capillaries were investigated for the enantioselective nano-LC separation of a group of racemic pharmaceuticals, namely, α- and β-blockers, anti-inflammatory drugs, antifungal drugs, norepinephrine-dopamine reuptake inhibitors, catecholamines, sedative hypnotics, antihistaminics, anticancer drugs, and antiarrhythmic drugs. Acceptable separation was achieved for many drugs using reversed phase chromatographic conditions with no separation achieved under normal phase conditions. Colistin sulfate appears to be useful addition to the available macrocyclic antibiotic chiral phases used in liquid chromatography.

Keywords: capillary chromatography; colistin sulfate; enantioselective; encapsulation; monolith; organic polymer.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structure of colistin sulfate (A) and teicoplanin (B).
Figure 2
Figure 2
SEM of column C1 at 1200× and 25,000× (left and right, respectively) shows small micro-globules with rough surface.
Figure 3
Figure 3
Chemical structures of the investigated racemates.
Figure 4
Figure 4
Enantioselective nano-LC separation of; (a) racemic 4-hydroxy-3-methoxymandelic acid (35); (b) phenylalanine (30) (mobile phase: methanol/water 40:60 v/v,); (c) tyrosine (29) and (d) O-methoxymandelic acid (34) on a C1 capillary column (150 µm ID, 25 cm length). UV: 219 nm, flow rate: 1 µL/min.
Figure 5
Figure 5
The loadability of the monolithic columns of 4-hydroxy-3-methoxymandelic acid (35) started at run no. 160 up to run no. 307, on C1 capillary column (150 µm ID, 25 cm length). mobile phase: methanol/water 40:60 v/v, UV: 219 nm, flow rate: 1 µL/min.
Figure 6
Figure 6
Steps showing the preparation of polymer monolithic capillary columns.
See this image and copyright information in PMC

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