[논문]Enantioselective electrophoretic behavior of lipoic acid in single and dual cyclodextrin systems

Le, Thi-Anh-Tuyet; Nguyen, Bao-Tan; Phan, Thanh Dung; Kang, Jong-Seong; Kim, Kyeong Ho

doi:10.5806/ast.2021.34.4.143

[국내논문] Enantioselective electrophoretic behavior of lipoic acid in single and dual cyclodextrin systems 원문보기

분석과학 = Analytical science & technology, v.34 no.4, 2021년, pp.143 - 152

Le, Thi-Anh-Tuyet (College of Pharmacy, Kangwon National University) , Nguyen, Bao-Tan (College of Pharmacy, Kangwon National University) , Phan, Thanh Dung (Faculty of Pharmacy, University of Medicine and Pharmacy) , Kang, Jong-Seong (College of Pharmacy, Chungnam National University) , Kim, Kyeong Ho (College of Pharmacy, Kangwon National University)

Abstract ▼ AI-Helper

Capillary electrophoresis (CE) is an effective technique to study chiral recognition because it offers flexibility in adjusting vital factors. Currently, various available cyclodextrins (CDs) can be employed for the chiral separation of numerous analytes. Herein, we investigate the enantioseparation behavior of lipoic acid enantiomers in various types of single and dual CD systems through CE. Additionally, several impacted CE parameters were optimized through the systematic investigation based on the design of experiment (DoE) concept for a single system comprising a heptakis (2,3,6-tri-O-methyl)-β-CD and a dual system containing the combination of the single CD with a sulfated-β-CD. Consequently, absolute enantioresolution was obtained within 15 min on a common standard bare fused-silica capillary (64.5/56 cm in total/effective length, 50/365 ㎛ inner/outer diameter), maintained at 15 ℃ and at an applied voltage of 24 kV. The optimal background electrolyte consisted of 6 mM heptakis (2,3,6-tri-O-methyl)-β-CD dissolved in the solution of 58 mM borate buffer at pH 10. Furthermore, the results of apparent binding constant experiments indicated that the S-enantiomer-heptakis (2,3,6-tri-O-methyl)-β-CD complex exhibited a stronger affinity than its R-enantiomer counterpart. The obtained electrophoretic mobility values could be utilized to interpret the resolution achieved at various CD concentrations and the mobility behavior of the complexes elucidated the migration order of the enantiomers in an electropherogram.

Keyword

표/그림 (10)

그림 Fig. 1. Chemical structure of alpha-lipoic acid enantiomers. (a) S-ALA, (b) R-ALA
그림 Fig. 2. The influence of pH on single TM-β-CD.
표 Table 1. Influence of BGE on the enantioseparation of dual CD systems
표 Table 2. p-values in ANOVA statistical parameters from screening results
그림 Fig. 3. 3D response surface plots of critical interactions in single CD system for resolution and migration time
표 Table 3. The optimization of single and dual CD system
그림 Fig. 4. Typical electropherograms of (a) Blank, (b) Standard solution, (c) Spiked S-ALA standard in R-α-lipoic tromethamine sample solution. CE condition: voltage, 24 kV; temperature, 15 ℃; injection time, 50 mbar in 3s; BGE, 58 mM sodium tetraborate pH 10 containing 6 mM TM-β-CD; PDA detector, 200 nm; current, 75 μA.
그림 Fig. 5. 3D response surface plots of interactions in dual CD system for resolution and migration time
그림 Fig. 6. Double-reciprocal plots for the complex of S-ALA and R-ALA with TM-β-CD
그림 Fig. 7. Difference in effective electrophoretic mobility between S-ALA and R-ALA complex

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대상 데이터

S-ALA and R-ALA standards were supplied by Sigma-Aldrich (Saint Louis, MO, USA). R-α-lipoic tromethamine was manufactured by Korea Biochem Pharm.
The surveyed β-CDs including β-CD, 2- hydroxypropyl-β-CD (HP-β-CD), methyl-β-CD (M- β-CD), acetyl-β-CD (A-β-CD), heptakis(2, 3, 6-tri-O- methyl)-β-CD (TM-β-CD) and sulfated-β-CD (S-β- CD) were purchased from Sigma-Aldrich (Saint Louis, MO, USA)

데이터처리

The list of 20 runs including four center points was carried out over 2 days. The critical factors for RSM were selected on the basis of the evaluation from the half-normal plot, pareto chart, ANOVA data and prediction models. The temperature, buffer concentration, and the TM-β-CD concentration demonstrated negligible effects on the responses (especially resolution and migration time) and were excluded for the reduced RSM design.

성능/효과

Furthermore, the results of the apparent binding constant experiments clearly explained the migration behavior and the robustness of each enantiomer complex as well as the chiral recognition ability of TM-β-CD over a range of concentrations.
Herein, the enantioselective behavior of lipoic acid was investigated by using single and dual CD systems. A reliable, fast, and effective CE-based method was developed to discriminate between the two enantiomers of lipoic acid.
The optimized method absolutely separated S- ALA and R-ALA with a favorable resolution (Rs = 1.65), using a common capillary, and within the shorter analysis time (15 minutes) than previous CE method. Furthermore, the results of the apparent binding constant experiments clearly explained the migration behavior and the robustness of each enantiomer complex as well as the chiral recognition ability of TM-β-CD over a range of concentrations.

후속연구

Among the 11 investigated combinations at pH 10, six dual systems were considered to be promising. Therefore, further studies to evaluate the effect of pH on these potential combinations were performed using suitable buffers. Unlike the single CD system, the dual system containing a mixture of TM-β-CD and a negatively charged CD (CM-β-CD, S-β-CD, and SBE-β-CD) displayed a synergistic relationship in term of separation efficiency.

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