Liquid chromatographic enantioseparation of β-blocking agents with (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propyl isothiocyanate as chiral derivatizing agent

Mamiro, Peter; Gyéresi, Árpád; Fülöp, Ferenc

doi:10.1016/s0021-9673(00)01229-2

Cited by 30 publications

(30 citation statements)

References 34 publications

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“…In addition, new CDRs were found to be more stable (>5 months at 2-5°C) as compared with CDRs based on DFDNB (Bhushan and Tanwar, 2009;Bhushan and Nagar, 2014a) and isothiocyanate (Kleidernigg et al, 1996;Péter et al, 2001;Péter and Fülöp, 2002). In addition, new CDRs were found to be more stable (>5 months at 2-5°C) as compared with CDRs based on DFDNB (Bhushan and Tanwar, 2009;Bhushan and Nagar, 2014a) and isothiocyanate (Kleidernigg et al, 1996;Péter et al, 2001;Péter and Fülöp, 2002).…”

Section: Stability Of Cdrs and Recovery Of Diastereomersmentioning

confidence: 87%

(RS)‐Propranolol: enantioseparation by HPLC using newly synthesized (S)‐levofloxacin‐based reagent, absolute configuration of diastereomers and recovery of native enantiomers by detagging

Alwera

Bhushan

2016

Biomedical Chromatography

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Diastereomers of (RS)-propranolol were synthesized using (S)-levofloxacin-based new chiral derivatizing reagents (CDRs). Levofloxacin was chosen as the pure (S)-enantiomer for its high molar absorptivity (εo ∼ 24000) and availability at a low price. Its -COOH group had N-hydroxysuccinimide and N-hydroxybenzotriazole, which acted as good leaving groups during nucleophilic substitution by the amino group of the racemic (RS)-propranolol; the CDRs were characterized by UV, IR, (1) H-NMR, high resolution mass spectrometry (HRMS) and carbon, hydrogen, nitrogen, and sulphur fundamental elemental components analyser (CHNS). Diastereomers were separated quantitatively using open column chromatography; absolute configuration of the diastereomers was established and the reagent moiety was detagged under microwave-assisted acidic conditions. (S)- and (R)-propranolol as pure enantiomers and (S)-levofloxacin were separated, isolated and characterized. Optimized lowest-energy structures of the diastereomers were developed using Gaussian 09 Rev. A.02 program and hybrid density functional B3LYP with 6-31G* basis set (based on density functional theory) for explanation of elution order and configuration. In addition, RP HPLC conditions for separation of diastereomers were optimized with respect to pH, concentration of buffer, flow rate of mobile phase and nature of organic modifier. HPLC separation method was validated as per International Conference on Harmonization guidelines. With the systematic application of various analytical techniques, absolute configuration of the diastereomers (and the native enantiomers) of (RS)-propranolol was established. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Stability Of Cdrs and Recovery Of Diastereomersmentioning

confidence: 87%

(RS)‐Propranolol: enantioseparation by HPLC using newly synthesized (S)‐levofloxacin‐based reagent, absolute configuration of diastereomers and recovery of native enantiomers by detagging

Alwera

Bhushan

2016

Biomedical Chromatography

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“…The literature reveals that a variety of CDRs have been used for enantioseparation of ( RS )‐Atl. These include CDRs based on: difluoro dinitro benzene (DFDNB) (Bhushan & Tanwar, , , ); cyanuric chloride (CC) (Batra & Bhushan, ; Bhushan & Dixit, ); isothiocyanates (Li, Yao, & Zeng, ; Péter, Gyéresi, & Fülöp, ); esters or anhydrides of carboxylic acids (Bhushan & Tanwar, ; Michael, Kevin, & Thomas, ; Rosseel et al, ); ( S )‐naproxen (Bhushan & Tanwar, ; Singh & Bhushan, ). …”

Section: Enantioseparation Of (Rs)‐atl By Indirect Approachmentioning

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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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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“…Figure 4 show chromatograms of β-blockers derivatized with GITC. The results show that the diastereomeric thiourea product from GITC and β-blocker eluted S-form first 6,13 . This result was confirmed with S-isomer of atenolol and metoprolol.…”

Section: Chromatographic Behavior Of the Derivativesmentioning

confidence: 91%

Development of a UPLC method with Chiral Derivatization for the Determination of Atenolol and Metoprolol Enantiomers in Tablet Preparations

Nguyen¹,

Pham²,

Nguyen³

et al. 2018

Pharm Sci Asia

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Liquid chromatographic enantioseparation of β-blocking agents with (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propyl isothiocyanate as chiral derivatizing agent

Cited by 30 publications

References 34 publications

(RS)‐Propranolol: enantioseparation by HPLC using newly synthesized (S)‐levofloxacin‐based reagent, absolute configuration of diastereomers and recovery of native enantiomers by detagging

(RS)‐Propranolol: enantioseparation by HPLC using newly synthesized (S)‐levofloxacin‐based reagent, absolute configuration of diastereomers and recovery of native enantiomers by detagging

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

Development of a UPLC method with Chiral Derivatization for the Determination of Atenolol and Metoprolol Enantiomers in Tablet Preparations

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