Enantiomeric purity determination of propranolol by capillary electrophoresis using dual cyclodextrins and a polyacrylamide-coated capillary

Assi, Khaled A.; Clark, Brian J.; Altria, Kevin D.

doi:10.1002/(sici)1522-2683(19990901)20:13<2723::aid-elps2723>3.3.co;2-f

Cited by 2 publications

(3 citation statements)

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“…An initial screening to determine the most significant factors affecting the chiral resolution of Prop and 4‐OH‐Prop was conducted using TEA/H 3 PO 4 and CM‐β‐CD in basic conditions. These conditions were selected based on the knowledge of the system acquired from initial experimental trials and on previously reported data for the resolution of Prop and/or 4‐OH‐Prop 20–26. The use of TEA/H 3 PO 4 and CM‐β‐CD in basic conditions resulted in a partial separation of drug and metabolite enantiomers.…”

Section: Resultsmentioning

confidence: 99%

“…The resolution of Prop enantiomers by CE, usually simultaneously with other chiral drugs, has been described in several papers using carboxymethyl‐β‐cyclodextrin (CM‐β‐CD) 20, 21, other β‐CD derivatives 22–24 or mixture of chiral selectors 25. In CE, the structure of the analytes can determine the choice of the cyclodextrin to be used.…”

Section: Introductionmentioning

confidence: 99%

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Theory of the Formation and Decomposition of N‐Heterocyclic Aminooxycarbenes through Metal‐Assisted [2+3]‐Dipolar Cycloaddition/Retro‐Cycloaddition

Novikov

Kuznetsov²,

Pombeiro³

2013

Chemistry A European J

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The theoretical background of the formation of N-heterocyclic oxadiazoline carbenes through a metal-assisted [2+3]-dipolar cycloaddition (CA) reaction of nitrones R(1)CH=N(R(2))O to isocyanides C≡NR and the decomposition of these carbenes to imines R(1)CH=NR(2) and isocyanates O=C=NR is discussed. Furthermore, the reaction mechanisms and factors that govern these processes are analyzed in detail. In the absence of a metal, oxadiazoline carbenes should not be accessible due to the high activation energy of their formation and their low thermodynamic stability. The most efficient promotors that could assist the synthesis of these species should be "carbenophilic" metals that form a strong bond with the oxadiazoline heterocycle, but without significant involvement of π-back donation, namely, Au(I), Au(III), Pt(II), Pt(IV), Re(V), and Pd(II) metal centers. These metals, on the one hand, significantly facilitate the coupling of nitrones with isocyanides and, on the other hand, stabilize the derived carbene heterocycles toward decomposition. The energy of the LUMO(CNR) and the charge on the N atom of the C≡N group are principal factors that control the cycloaddition of nitrones to isocyanides. The alkyl-substituted nitrones and isocyanides are predicted to be more active in the CA reaction than the aryl-substituted species, and the N,N,C-alkyloxadiazolines are more stable toward decomposition relative to the aryl derivatives.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Theory of the Formation and Decomposition of N‐Heterocyclic Aminooxycarbenes through Metal‐Assisted [2+3]‐Dipolar Cycloaddition/Retro‐Cycloaddition

Novikov

Kuznetsov²,

Pombeiro³

2013

Chemistry A European J

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“…Among neutral cyclodextrins, β‐cyclodextrins have been demonstrated to be the most selective for propranolol but allowing only moderate resolution. Different strategies have been used to improve resolution at low pH such as using charged substituted β‐cyclodextrins [], the addition of organic modifiers [], the use of coated capillaries, or the use of mixtures of cyclodextrins [].…”

Section: Resultsmentioning

confidence: 99%

Electroosmotic flow modulation in capillary electrophoresis by organic cations from ionic liquids

et al. 2012

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This paper describes the ability of several ionic liquids cations for electroosmotic flow modulation in capillary electrophoresis. Organic salts based on phosphonium, sulfonium, cysteinium, ammonium, and guanidinium cations were selected to study this property. In addition, the synergistic effect of these compounds in cyclodextrin chiral separation was also evaluated. In comparison with most studied imidazolium-based ionic liquids, several of the cations studied, are stronger modifiers in terms of electroosmotic flow (EOF) modulation. Phosphonium-based compounds and tri-octyl methylammonium chloride ([Aliquat]Cl) had the strongest ability to reverse EOF both in acidic and in basic conditions and had the lowest EOF reversal concentrations in the presence of hydroxypropyl-β-cyclodextrin. EOF modulation ability of phosphonium cations also contributed to the improvement of chiral separation of DL-propranolol by hydroxypropyl-β-cyclodextrin at lower concentrations in comparison with most commonly used EOF modulators such as tetrabutylammonium phosphate.

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Enantiomeric purity determination of propranolol by capillary electrophoresis using dual cyclodextrins and a polyacrylamide-coated capillary

Cited by 2 publications

References 0 publications

Theory of the Formation and Decomposition of N‐Heterocyclic Aminooxycarbenes through Metal‐Assisted [2+3]‐Dipolar Cycloaddition/Retro‐Cycloaddition

Theory of the Formation and Decomposition of N‐Heterocyclic Aminooxycarbenes through Metal‐Assisted [2+3]‐Dipolar Cycloaddition/Retro‐Cycloaddition

Electroosmotic flow modulation in capillary electrophoresis by organic cations from ionic liquids

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