Enantioseparation of atenolol using chiral ligand-exchange chromatography on C8 column

Alizadeh, Taher

doi:10.1016/j.seppur.2013.08.032

Cited by 12 publications

(14 citation statements)

References 37 publications

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“…This technique of chiral LEC is usually employed in three separate forms: (a) the ‘chiral‐bonded ligand exchanging stationary phases’ where the chiral selector is covalently attached to the stationary phase; (b) ligand exchanging columns that are easily prepared from commercially available reversed‐phase columns by dynamically coating the column with a hydrophobic chiral selector; and (c) the chiral selector predominantly resides in the mobile phase (Alizadeh, ).…”

Section: Enantioresolution By Ligand‐exchange Chromatography (Lec)mentioning

confidence: 99%

“…The side chains of both l ‐Ala and ( S )‐Atl in the case of pseudohomochiral complex are on the same side in the space, whereas the side chains of l ‐Ala and ( R )‐Atl in the case of pseudo‐heterochiral complex are on opposite sides. This leads to stronger hydrophobic interactions of the pseudo‐homochiral complex with the stationary phase, leading to longer retention time of ( S )‐Atl, compared with that of ( R )‐Atl (Alizadeh, ).…”

Section: Enantioresolution By Ligand‐exchange Chromatography (Lec)mentioning

confidence: 99%

See 1 more Smart Citation

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

Batra

Bhushan

2017

Biomedical Chromatography

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Atenolol, a β-adrenergic receptor antagonist, is a chiral compound used for the treatment of cardiovascular diseases and to treat hypertension, coronary heart disease, arrhythmias, sinus tachycardia and myocardial infarction, where it acts preferentially upon the β-adrenergic receptors in the heart. It is marketed as a racemate, but only the (S)-enantiomer of (RS)-atenolol is responsible for the β-adrenoceptor blocking activity. Different chromatographic methods have been applied for the separation and determination of enantiomers. In this article a review is presented on liquid chromatographic methods for enantioseparation of (RS)-atenolol by both direct and indirect approaches involving practical applications of several chiral stationary phases, chiral derivatization reagents and ligand exchange and impregnation methods. These include methods using both HPLC and TLC for separation, determination and bioassay of enantiomers of atenolol. In addition, some aspects of enantioseparation under achiral phases of liquid chromatography have been briefly mentioned as applicable to (RS)-atenolol. This review provides current available enantioseparation choices not only for (RS)-atenolol but also for other applicable racemic drugs.

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Section: Enantioresolution By Ligand‐exchange Chromatography (Lec)mentioning

confidence: 99%

Section: Enantioresolution By Ligand‐exchange Chromatography (Lec)mentioning

confidence: 99%

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

Batra

Bhushan

2017

Biomedical Chromatography

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“…Analytes to be resolved form the mixed-ligand complexes with the selector, which are diastereomeric in their structure. Marfey's reagent UV [118] HPLC Penicillamine TLC Amino acids Marfey's reagent and its chiral variants as CDR UV-340 nm [156] TLC and HPLC Penicillamine Marfey's reagent UV-340 nm [157] TLC and HPLC Non-protein α-amino acids Marfey's reagent and its four variants UV-340 nm [154] Such diastereomers interact differently with the column packing and hence get separated [71][72][73][74]. Schmid et al [75] highlighted their own research developments on chiral separation using the principle of ligand-exchange.…”

Section: Copper (Ii) Amino Acid Complexes As Reagents In Lecmentioning

confidence: 99%

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

Tanwar

Bhushan

2015

Chromatographia

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“…k e and k s are the first-order apparent rate constants of the extraction and stripping processes, respectively. The following equations can be proposed for the kinetic model [31]. …”

Section: Effect Of Transport Time and Kinetic Modelingmentioning

confidence: 99%

Synthesis of a nano‐sized chiral imprinted polymer and its use as an (S)‐atenolol carrier in the bulk liquid membrane

Alizadeh

2014

J of Separation Science

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In this work, nanosized chiral imprinted polymers containing (S)-atenolol ((S)-ATN) selective sites were synthesized by using suspension polymerization in silicon oil. (S)-ATN, methacrylic acid, and ethylene glycol dimethacrylate were used as enantiomerically pure template, functional monomer, and cross-linker, respectively. The prepared chiral imprinted polymers were used as the carrier elements in a bulk liquid membrane (BLM). (S)-ATN transport capability of the chiral imprinted polymers was compared with that of the nonimprinted polymer. It was shown that chiral imprinted polymers could transport (S)-ATN through the BLM more effectively than (R)-ATN, whereas no difference in the facilitated transport was observed between (R)-ATN and (S)-ATN when using nonimprinted polymer particles as the carrier element in the BLM. A kinetic model was proposed for the transportation of (S)-ATN through the chiral imprinted polymers based BLM. It was found that the extraction of ATN from the source to the membrane controls the chiral separation process. It was also found that the pH of source and receiving phases as well as the racemic ATN concentration in source phase had very crucial effect on the chiral separation efficiency.

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Enantioseparation of atenolol using chiral ligand-exchange chromatography on C8 column

Cited by 12 publications

References 37 publications

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

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

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

Synthesis of a nano‐sized chiral imprinted polymer and its use as an (S)‐atenolol carrier in the bulk liquid membrane

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