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Interaction of native α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin and their hydroxypropyl derivatives with selected organic low molecular mass compounds at elevated and subambient temperature under RP-HPLC conditions

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Abstract

The main focus of this study was to explore the capability of native α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin and their hydroxypropyl derivatives for host-guest interaction with 7,8-dimethoxyflavone, selected steroids (estetrol, estriol, estradiol, estrone, testosterone, cortisone, hydrocortisone, progesterone and 17α-hydroxyprogesterone) and polycyclic aromatic hydrocarbons (toluene, naphthalene, 1,8-dimethylnaphthalene, 1-acenaphthenol, acenaphthylene and acenaphthene) under reversed-phase liquid-chromatography conditions. The study revealed that native cyclodextrins interact more efficiently with the analytes investigated than do their hydroxypropyl counterparts. In the low-temperature region, enormously high ratios were observed for polycyclic aromatic hydrocarbons, particularly 1,8-dimethylnaphthalene, acenaphthene and acenaphthylene chromatographed on a β-cyclodextrin-modified mobile phase. In such a case, the retention times of the polycyclic aromatic hydrocarbons were strongly reduced (e.g. from 127 to 1.2 min for 1,8-dimethylnaphthalene) and were close to the hold-up time of the high-performance liquid chromatography (HPLC) system (0.7 min). Moreover, chiral separation of 1-acenaphthenol optical isomers was observed and the elution order of the enantiomers was determined. Within the steroids group, strong interaction was observed for estradiol and testosterone. The results of cluster analysis indicate that β-cyclodextrin as well as γ-cyclodextrin and its hydroxypropyl derivative can be most effective mobile-phase additives under reversed-phase HPLC conditions for 3D-shape-recognition-driven separation, performed at subambient and elevated temperatures, respectively.

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Acknowledgement

P.K.Z. gratefully acknowledges financial support from the Japan Society for the Promotion of Science (JSPS).

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Authors and Affiliations

  1. Section of Toxicology and Bioanalytics, Department of Environmental Biology, Koszalin University of Technology, Śniadeckich 2, 75-453, Koszalin, Poland

    P. K. Zarzycki

  2. School of Materials Science, Toyohashi University of Technology, Toyohashi, 441-8580, Japan

    H. Ohta, Y. Saito & K. Jinno

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  1. P. K. Zarzycki
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  2. H. Ohta
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  3. Y. Saito
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  4. K. Jinno
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Correspondence to P. K. Zarzycki.

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Zarzycki, P.K., Ohta, H., Saito, Y. et al. Interaction of native α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin and their hydroxypropyl derivatives with selected organic low molecular mass compounds at elevated and subambient temperature under RP-HPLC conditions. Anal Bioanal Chem 391, 2793–2801 (2008). https://doi.org/10.1007/s00216-008-2209-3

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  • DOI: https://doi.org/10.1007/s00216-008-2209-3

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