Retention behavior of proton pump inhibitors using immobilized polysaccharide-derived chiral stationary phases with organic-aqueous mobile phases

Cirilli, Roberto; Ferretti, Rosella; Gallinella, Bruno; Zanitti, Leo

doi:10.1016/j.chroma.2013.07.021

Cited by 29 publications

(28 citation statements)

References 29 publications

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“…Obviously, on CSPs 2 and 3 , the retention mechanism of 7 and 12 changed depending on the amount of H 2 O. Indeed, as previously observed by other authors , a competition between water and analyte can occur as both interact with the binding sites of the polysaccharide selector. Thus, two types of mechanisms can be involved: (i) at lower concentrations (10%), water behaves as the strongest solvent as it occurs under HILIC conditions (Fig.…”

Section: Resultssupporting

confidence: 54%

High‐performance liquid chromatography enantioseparation of polyhalogenated 4,4′‐bipyridines on polysaccharide‐based chiral stationary phases under multimodal elution

Peluso

Mamane

Aubert

et al. 2014

J of Separation Science

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An investigation on the high-performance liquid chromatography enantioseparation of 12 polyhalogenated 4,4'-bipyridines on polysaccharide-based chiral stationary phases is described. The overall study was directed toward the generation of efficient separations in order to obtain pure atropisomers that will serve as ligands for building homochiral metal organic frameworks. Four coated columns--namely, Lux Cellulose-1, Lux Cellulose-2, Lux Cellulose-4, and Lux Amylose-2--and two immobilized columns--namely, Chiralpak IC and IA--were used under normal, polar organic, and reversed-phase elution modes. Moreover, Chiralcel OJ was considered under normal-phase and polar organic conditions. The effect of the chiral selector and mobile phase composition on the enantioseparation, the enantiomer elution order and the beneficial effect of nonstandard solvents were studied. The effect of water in the mobile phase on the enantioselectivity and retention was investigated and retention profiles typical of hydrophilic interaction liquid chromatography were observed. Interesting phenomena of solvent-induced enantiomer elution order reversal occurred under normal-phase mode. All the considered 4,4'-bipyridines were enantioseparated at the multimilligram level.

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Section: Resultssupporting

confidence: 54%

High‐performance liquid chromatography enantioseparation of polyhalogenated 4,4′‐bipyridines on polysaccharide‐based chiral stationary phases under multimodal elution

Peluso

Mamane

Aubert

et al. 2014

J of Separation Science

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“…The curves obtained by plotting the retention factors of both enantiomers versus the water content in the binary mobile phases are shown in Figure . In agreement with what already evidenced in correlated researches involving other polysaccharide‐based CSPs , the U‐shape retention plots obtained in ACN‐aqueous mode highlight two different regions, which are associated with two complementary retention mechanisms. On the left side of the U‐turn point, the decreasing zone is characterized by a water‐poor region (<40 vol) in which the water acts as the strongest eluting solvent.…”

Section: Resultssupporting

confidence: 90%

“…The column temperature was set at 25 • C. The curves obtained by plotting the retention factors of both enantiomers versus the water content in the binary mobile phases are shown in Figure 1. In agreement with what already evidenced in correlated researches involving other polysaccharide-based CSPs [11][12][13][14][15], the U-shape retention plots obtained in ACN-aqueous mode highlight two different regions, which are associated with two complementary On the left side of the U-turn point, the decreasing zone is characterized by a water-poor region (<40 vol) in which the water acts as the strongest eluting solvent. Within this zone, which is commonly assigned to HILIC mode, any increase in water content in the mobile phase brings about a decrease in retention of both enantiomers of OXFZ.…”

Section: Analytical Hplc Enantioseparation Under Organic-aqueous Condsupporting

confidence: 89%

“…[7] and Okamoto et al [8] on the HILIC-like behavior of polysaccharide-based CSPs are dated around two decades ago, there is a general tendency to classify as RP enantioseparation each enantioselective analysis carried out with organic-aqueous eluents. Actually, as highlighted just in a few works [9][10][11][12][13][14][15][16], the polysaccharide-based materials can behave T A B L E 1 Chromatographic results in polar organic conditions as classical RP-like CSPs, and at the same time as HILIC-like CSPs, depending on the content of water in mobile phase (i.e. under HILIC domain the content of water is usually lower than 40%).…”

Section: Introductionmentioning

confidence: 99%

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A chromatographic study on the retention behavior of the amylose tris(3‐chloro‐5‐methylphenylcarbamate) chiral stationary phase under aqueous conditions

Cirilli

Carradori

Casulli

et al. 2018

J of Separation Science

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In this study, the retention properties of the immobilized polysaccharide-derived Chiralpak IG-3 chiral stationary phase under aqueous-organic conditions were investigated. A systematic evaluation of the retention factors of the enantiomers of the chiral sulfoxide oxfendazole, endowed with anthelmintic activity and selected as test compound, was carried out changing progressively the water content in hydro-organic eluents containing methanol, ethanol or acetonitrile. From the results obtained with acetonitrile/water mobile phases and the associated retention plots, clear U-shape retention dependencies, indicative of the interplay of both hydrophilic interaction liquid chromatography and reversed-phase modes, were highlighted. A U-turn point of retention mechanism was recorded in correspondence of the acetonitrile/water 100:40 v/v mobile phase. Retention was significantly affected by small percentages of trifluoroacetic acid or diethylamine additives incorporated in the mobile phase. It is worth emphasizing that the basic additive was more effective in reducing retention in the reversed-phase region, while the action of acid additive was more pronounced in the hydrophilic interaction liquid chromatography region. Finally, either in the transition from hydrophilic interaction liquid chromatography to reversed-phase conditions or after additive addition, the enantioselectivity did not vary significantly.

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“…The absolute configuration of collected enantiomers was assigned by comparing the CD spectra measured in ethanol with the data reported in the literature [15,17].…”

Section: Enantiomer Elution Order Assignmentmentioning

confidence: 99%

Green high-performance liquid chromatography enantioseparation of lansoprazole using a cellulose-based chiral stationary phase under ethanol/water mode

et al. 2016

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A simple and environmentally friendly reversed-phase high-performance liquid chromatography method for the separation of the enantiomers of lansoprazole has been developed. The chromatographic resolution was carried out on the cellulose-based Chiralpak IC-3 chiral stationary phase using a green and low-toxicity ethanol-aqueous mode. The effects of water content in the mobile phase and column temperature on the retention of the enantiomers of lansoprazole and its chiral and achiral related substances have been carefully investigated. A mixed-mode hydrophilic interaction liquid chromatography and reversed-phase retention mechanism operating on the IC-3 chiral stationary phase allowed us to achieve simultaneous enantioselective and chemoselective separations in water-rich conditions. The enantiomers of lansoprazole were baseline resolved with a mobile phase consisting of ethanol/water 50:50 without any interference coming from chiral and achiral impurities within 10 min.

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Retention behavior of proton pump inhibitors using immobilized polysaccharide-derived chiral stationary phases with organic-aqueous mobile phases

Cited by 29 publications

References 29 publications

High‐performance liquid chromatography enantioseparation of polyhalogenated 4,4′‐bipyridines on polysaccharide‐based chiral stationary phases under multimodal elution

High‐performance liquid chromatography enantioseparation of polyhalogenated 4,4′‐bipyridines on polysaccharide‐based chiral stationary phases under multimodal elution

A chromatographic study on the retention behavior of the amylose tris(3‐chloro‐5‐methylphenylcarbamate) chiral stationary phase under aqueous conditions

Green high-performance liquid chromatography enantioseparation of lansoprazole using a cellulose-based chiral stationary phase under ethanol/water mode

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