Effect of Sulfobutyl Ether Beta-Cyclodextrin Modifier on Selectivity of Reversed Phase HPLC Separations

Ngim, Kenley K.; Zhong, Qiqing; Mistry, Kavita; Chetwyn, Nik P.

doi:10.1080/10826076.2011.639116

Cited by 10 publications

(11 citation statements)

References 44 publications

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“…For similar methods published in literature, no selectivity was reported. On the other hand, resolution was measured instead [33], or it was stated as no separation for TER was achieved on octadecylsilane with the use of HP-βCD in the mobile phase [31]. Other reports using native beta cyclodextrins as CMPA rather than using substituted ones showed slightly lower selectivity values for TER to the values in our study [32].…”

Section: Discussioncontrasting

confidence: 61%

“…A moderate concentration (3-8 mM) of SBE-β-CD led to a good separation at a wide range of buffer concentration (5-50 mM, Figure 6B). A mixed modal interaction involving ion pairing, hydrogen bonding, and inclusion complex at the hydrophobic cavity are most likely occurring [33]. Separation in a slightly acidic medium (pH = 3.5) guarantees the unionization of some sulfonic groups (pKa = 2), where partitioning with the reversed phase takes place along with the presence of some other ionized sulfonic groups eluting in the mobile phase paired with TER.…”

Section: Discussionmentioning

confidence: 99%

“…Guidelines request the consideration of each enantiomer of pharmaceuticals as single active compounds [30]. Hence, TER enantiomers were chiraly resolvedamong many methodologies-using native and substituted beta cyclodextrins as CMPA by capillary electrophoresis (CE) and HPLC [25,[31][32][33][34]. Despite the availability of numerous reports regarding TER enantioseparation in the literature, no understanding of the mechanistics of chiral recognition has ever been reported [15,35,36], likely because all reports use a one-factor-at-a-time (OFAT) approach during optimization, leaving factors' interactions unexamined.…”

Section: Introductionmentioning

confidence: 99%

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Quality-by-Design Is a Tool for Quality Assurance in the Assessment of Enantioseparation of a Model Active Pharmaceutical Ingredient

2020

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The design of experiments (DoE) is one of the quality-by-design tools valued in analytical method development, not only for cost reduction and time effectiveness, but also for enabling analytical method control and understanding via a systematic workflow, leading to analytical methods with built-in quality. This work aimed at using DoE to enhance method understanding for a developed UHPLC enantioseparation of terbutaline (TER), a model chiral drug, and to define quality assurance parameters associated with using chiral mobile phase additives (CMPA). Within a response surface methodology workflow, the effect of different factors on both chiral resolution and retention was screened and optimized using Plackett-Burman and central composite designs, respectively, followed by multivariate mathematical modeling. This study was able to delimit method robustness and elucidate enantiorecognition mechanisms involved in interactions of TER with the chiral modifiers. Among many CMPAs, successful TER enantioresolution was achieved using hydroxypropyl β-cyclodextrin (HP-β-CD) added to the mobile phase as 5.4 mM HP-β-CD in 52.25 mM ammonium acetate. Yet, limited method robustness was observed upon switching between the different tested CMPA, concluding that quality can only be assured with specific minimal pre-run conditioning time with the CMPA, namely 16-column volume (60 min at 0.1 mL/min). For enantiorecognition understanding, computational molecular modeling revealed hydrogen bonding as the main binding interaction, in addition to dipole-dipole inside the CD cavity for the R enantiomer, while the S enantiomer was less interactive.

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Section: Discussioncontrasting

confidence: 61%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quality-by-Design Is a Tool for Quality Assurance in the Assessment of Enantioseparation of a Model Active Pharmaceutical Ingredient

2020

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“…Enantioseparation of Orc has been carried out in the present case via synthesis of diastereomeric derivatives with CDRs 1–6, diastereomeric derivatives of Orc prepared with CDR 1 were separated with the R s 8.84, which is better than enantioseparation of Orc reported in literature 8.26 with ( R )‐5‐fluoro‐2,4‐dinitro‐ n ‐(1‐phenylethyl)benzenamine [8] by indirect approach and R s is also higher than that obtained using chiral column (direct approach), for example, R s was 0.8 using sulfobutyl ether β‐cyclodextrin [6], 4.68 using cellulose tris(3,5‐dimethylphenylcarbamate) [20], 2.03 using sulfated‐β‐cyclodextrin [21], and 3.95 using methyl‐β‐cyclodextrin [22]. A comparison of R s and LOD by direct approach using different CSPs, chiral selectors, and chiral inducing reagents (CIRs) is presented in Table 3.…”

Section: Resultsmentioning

confidence: 87%

“…In literature, both direct and indirect approaches have been reported to achieve enantioseparation of Bel and Orc. HPLC resolution of enantiomers of Bel [2][3][4][5][6] and that of Orc [6] by direct approach has been carried out using certain chiral stationary phases (CSPs).…”

Section: Introductionmentioning

confidence: 99%

Microchemical enantioseparation of betaxolol and orciprenaline by reversed phase HPLC

Nagar

Vyas

Bhushan

2020

Separation Science Plus

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Enantioseparation of (RS)-orciprenaline and (RS)-betaxolol was achieved by synthesizing their diastereomeric derivatives with chiral derivatizing reagents prepared on a cyanuric chloride platform. There were three dichloro-triazine derivatives with amino acid amides as chiral auxiliaries and three monochlorotriazine derivatives with methoxy as achiral moiety and amino acid amides as chiral auxiliaries in cyanuric chloride. A total of 12 pairs of diastereomeric derivatives were synthesized under microwave irradiation and were separated using reversed phase high-performance liquid chromatography by applying different mobile phases on a C 18 column in gradient eluting mode with ultraviolet detection at 230 nm. Resolutions were compared and interpreted on the basis of structure of chiral auxiliaries. Besides, diastereomeric derivatives were separated by open column chromatography and the samples so obtained were used for confirmation of their elution order and configuration by 1 H-NMR spectroscopy. In addition, lowest energy optimized structures of diastereomeric derivatives were developed using the density functional theory based Gaussian software that were interpreted to supplement the absolute configurations. The method validation was carried out for detection limit, linearity, accuracy, and precision. Limits of detection were 0.005 and 0.007 µg/mL.

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Adsorption of naphthenic acids from oil sand process‐affected water with water‐insoluble poly(β‐cyclodextrin‐citric acid)

Liang

Zou

2019

Can J Chem Eng

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With polyvinyl alcohol as the main chain, a water‐insoluble poly(β‐cyclodextrin‐citric acid) was prepared as a supramolecular adsorbent for the treatment of oil sand process‐affected water (OSPW) containing naphthenic acids (NAs). FT‐IR, TGA, and SEM were used for the characterization of adsorbent, and an automatic infrared oil analyzer was used to monitor the concentration change of NAs in the water. The adsorption behaviour and mechanism were explored by adsorption kinetics and thermodynamic studies. The results showed that the adsorption process could be described well with the Langmuir isothermal adsorption model and quasi‐second‐order kinetic model, which indicated that the host‐guest interaction of β‐cyclodextrin promoted the adsorption of NAs. The discussion regarding pH indicated that the neutral condition (pH = 7) was considered the best. In addition, a molecular dynamics simulation was carried out using a Materials Studio package purchased from Accelrys to verify that the structure with polyvinyl alcohol as main chain was beneficial to adsorption. The excellent adsorption capacity (qmax was 193.42 mg · g−1) and reusability of the poly(β‐cyclodextrin‐citric acid) indicated its potential as practical adsorbent for the treatment of OSPW.

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Effect of Sulfobutyl Ether Beta-Cyclodextrin Modifier on Selectivity of Reversed Phase HPLC Separations

Cited by 10 publications

References 44 publications

Quality-by-Design Is a Tool for Quality Assurance in the Assessment of Enantioseparation of a Model Active Pharmaceutical Ingredient

Quality-by-Design Is a Tool for Quality Assurance in the Assessment of Enantioseparation of a Model Active Pharmaceutical Ingredient

Microchemical enantioseparation of betaxolol and orciprenaline by reversed phase HPLC

Adsorption of naphthenic acids from oil sand process‐affected water with water‐insoluble poly(β‐cyclodextrin‐citric acid)

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