8
MA ET AL.
lomefloxacin in human plasma. J Pharm Biomed Anal. 1995;
13(10):1243-1248.
8. Lehr KH, Damm P. Quantification of the enantiomers of
ofloxacin in biological fluids by high-performance liquid
chromatography. J Chromatogr. 1988;425:153-161.
OFLX, corresponding to the enantioseparation of OFLX
at pH 2.5–5.0. Table 3 listed the data of the calculated
binding energy of OFLX R,S-enantiomer interacted with
S-β-CD.
9. Zeng S, Zhong J, Pan L, Li Y. High-performance liquid chroma-
tography separation and quantification of ofloxacin enantio-
mers in rat microsomes. J Chromatogr B. 1999;728(1):151-155.
10. Suntornsuk L. Recent advances of capillary electrophoresis in
pharmaceutical analysis. Anal Bioanal Chem. 2010;398(1):
29-52.
11. Pan C, Wang W, Chen X. Recent developments of chiral sepa-
ration by capillary electrophoresis. Chin J Chromatogr. 2016;
34(1):16-20.
12. Xiao Y, Ng SC, Tan TT, Wang Y. Recent development of
cyclodextrin chiral stationary phases and their applications in
chromatography. J Chromatogr A. 2012;1269:52-68.
13. Potiera IL, Tamisier-Karolaka SL, Morinb P, Megelc F,
Tavernaa M. Comparison of native, alkylated and charged
cyclodextrins for the chiral separation of labetalol stereoiso-
mers by capillary electrophoresis. J Chromatogr A. 1998;
829(1-2):341-349.
14. Yue J, Cheng C, Meng L, Chen J, Li M, Zhu Z. Simultaneous
and sensitive capillary electrophoretic enantioseparation of
three β-blockers with the combination of achiral ionic liquid
and dual CD derivatives. Talanta. 2012;89:149-154.
15. Li W, Zhao L, Zhang H, et al. Enantioseparation of new
triadimenol antifungal active compounds by electrokinetic
chromatography and molecular modeling study of chiral recog-
nition mechanisms. Electrophoresis. 2014;35(19):2855-2862.
16. Zhao M, Cui Y, Yu J, Xu S, Guo X. Combined use
of hydroxypropyl-cyclodextrin and ionic liquids for the
simultaneous enantioseparation of four azole antifungals by
CE and a study of the synergistic effect. J Sep Sci. 2014;37(1-2):
151-157.
4 | CONCLUSION
In this work, S-β-CD with the degree of substitution
of 7–11 was applied for efficient enantioseparation
of four chiral FQs, namely, ofloxacin, gemifloxacin,
lomefloxacin, and gatifloxacin. The important parameters
affected the enantioseparation, such as the concentra-
tions of chiral selector, BGE pH and buffer types and con-
centrations were optimized. Further, the enantiomeric
recognition mechanism of S-β-CD was also investigated
by combining the experimental results and molecular
docking study. It was indicated that the electrostatic
attraction between the enantiomer and S-β-CD played an
crucial role in chiral discrimination. This work provided
not only a applicable method for enantioseparation of
chiral FQs, but also a new insight into the chiral recogni-
tion mechanism of S-β-CD.
DATA AVAILABILITY STATEMENT
Research data are not shared.
ORCID
REFERENCES
17. Yu J, Zhao Y, Song J, Guo X. Enantioseparation of meptazinol
and its three intermediate enantiomers by capillary electropho-
resis using a new cationic β-cyclodextrin derivative in single
and dual cyclodextrin systems. Biomed Chromatogr. 2014;28(6):
868-874.
1. Drusano G, Labro-T M, Cars O, et al. Pharmacokinetics and
pharmacodynamics of fluoroquinolones. Clin Microbiol Infect.
1998;4:2S27-2S41.
2. Zhou S, Ouyang J, Baeyens WRG, Zhao H, Yang Y. Chiral
separation of four fluoroquinolone compounds using capillary
electrophoresis with hydroxypropyl-cyclodextrin as chiral
selector. J Chromatogr A. 2006;1130(2):296-301.
3. Morrissey I, Hoshino K, Sato K, et al. Mechanism of
differential activities of ofloxacin enantiomers. Antimicrob
Agents Chemother. 1996;40(8):1775-1784.
4. Hassan RM, Yehia AM, Saleh OA, El-Azzouny AA,
Aboul-Enein HY. Structure-retention relationship for enantio-
separation of selected fluoroquinolones. Chirality. 2018;30(6):
828-836.
5. Zhang Z, Yang G, Wang D, Liang G, Chen Y. Chiral Separation
and enantiomeric purity determination of pazufloxacin
mesilate by HPLC using chiral mobile phase additives. J Liq
Chromatogr R T. 2004;27(5):813-827.
ꢀ
18. Gomara B, García-Ruiz C, Marina ML. Enantioselective
separation of the sunscreen agent 3-(4-methylbenzylidene)-
camphor by electrokinetic chromatography: quantitative
analysis in cosmetic formulations. Electrophoresis. 2005;26(20):
3952-3959.
19. Fonseca MC, Silva RCSD, Nascimento CS, Borges KB.
Computational contribution to the electrophoretic enantiomer
separation mechanism and migration order using modified
β-cyclodextrins. Electrophoresis. 2017;38(15):1860-1868.
20. Zhou L, Lun J, Liu Y, Jiang Z, Di X, Guo X. In situ immobiliza-
tion of sulfated-β-cyclodextrin as stationary phase for capillary
electrochromatography enantioseparation. Talanta. 2019;
200:1-8.
21. Lin CE, Ko TC, Kuo CM, et al. Determination of
enantiomerization barrier of thioridazine by dynamic capillary
electrophoresis using sulfated cyclodextrins as chiral selectors.
Electrophoresis. 2009;30(17):3071-3078.
6. Grellet J, Ba B, Saux MC. High-performance liquid
chromatographic separation of fluoroquinolone enantiomers: a
review. J Biochem Biophys Methods. 2002;54(1-3):221-233.
7. Foster RT, Carr RA, Pasutto FM, Longstreth JA. Stereospecific
22. Wang Z, Zhang Q, Luo L, Sun T, Guo X. Comparison of three
S-β-CDs with different degrees of substitution for the chiral
high-performance
liquid
chromatographic
assay
of