Interaction of native alpha-cyclodextrin, beta-cyclodextrin and gamma-cyclodextrin and their hydroxypropyl derivatives with selected organic low molecular mass compounds at elevated and subambient temperature under RP-HPLC conditions.
The main focus of this study was to explore the capability of native alpha-cyclodextrin, beta-cyclodextrin and gamma-cyclodextrin and their hydroxypropyl derivatives for host-guest interaction with 7,8-dimethoxyflavone, selected steroids (estetrol, estriol, estradiol, estrone, testosterone, cortisone, hydrocortisone, progesterone and 17alpha-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 beta-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 beta-cyclodextrin as well as gamma-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.
Section of Toxicology and Bioanalytics, Department of Environmental Biology, Koszalin University of Technology, Sniadeckich 2, 75-453, Koszalin, Poland. pkzarz@wp.pl
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Zarzycki
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Ohta
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Saito
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Jinno
D000073738:2-Hydroxypropyl-beta-cyclodextrin; D002851:Chromatography, High Pressure Liquid / Q000145:classification / Q000379:methods; D002942:Circular Dichroism; D008958:Models, Molecular; D015394:Molecular Structure; D008970:Molecular Weight; D009844:Oligosaccharides / Q000737:chemistry; D009930:Organic Chemicals / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry; D013256:Steroids / Q000737:chemistry; D013696:Temperature; D047391:alpha-Cyclodextrins / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*; D047408:gamma-Cyclodextrins / Q000737:chemistry*
C402302:(2-hydroxypropyl)-alpha-cyclodextrin; D009844:Oligosaccharides; D009930:Organic Chemicals; D011084:Polycyclic Aromatic Hydrocarbons; D013256:Steroids; D047391:alpha-Cyclodextrins; D047392:beta-Cyclodextrins; D047408:gamma-Cyclodextrins; D000073738:2-Hydroxypropyl-beta-cyclodextrin; C023792:gamma-cyclodextrin; C032613:alpha-cyclodextrin