Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography

Zarzycki, Paweł K.; Włodarczyk, Elżbieta; Baran, Michał J.

doi:10.1016/j.chroma.2009.03.067

Cited by 17 publications

(17 citation statements)

References 28 publications

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“…At ambient and subambient temperature regions, baseline separation of 1-acenaphthenol enantiomers is observed, which is associated with fast peaks elution from the column (and deviation from Van’t Hoff plot), due to interaction with β-CD additive low retarded by stationary phase. This phenomenon was observed before and documented experimentally for various low-molecular mass chiral and achiral molecules (including polycyclic aromatic hydrocarbons, steroids, and bisphenols) chromatographed under similar conditions [9, 41–43]. As can be seen from plots a2 and b2 presented within Fig.…”

Section: Resultssupporting

confidence: 81%

“…Our investigation revealed that this problem does not exist for a number of various analytes and very well mobile phase soluble hydroxypropyl derivative of β-cyclodextrin (Fig. S1 in the ESM) [41]. In case of native β-CD additive, potential problem was observed for two steroids: progesterone and 20α-hydroxyprogesterone eluted for temperatures below 10 °C.…”

Section: Resultsmentioning

confidence: 97%

“…In practice, retention behavior of mobile phase macrocyclic additive can be precisely adjusted by concentration of organic solvent of binary liquids (e.g., by applying acetonitrile in water mixtures close to 35%; v / v ), which can be easily visualized by planar chromatography experiments [38, 39, 64]. We presented a number of experimental data indicating that reversed-phase chromatographic systems, where cyclodextrin additive is weakly retarded by stationary phase (close to the retention volume of dead volume marker), are extremely temperature sensitive, and allow massive retention and selectivity changes for given low-molecular mass compounds [41]. Moreover, we documented that retention of inclusion complexes based on cyclodextrins as the host molecules can be varied between two lines formed by the Van’t Hoff plot of free cyclodextrin and the Van’t Hoff plot of the uncomplexed solute [15, 42, 43].…”

Section: Resultsmentioning

confidence: 99%

“…Temperature effects on chromatographic retention involving mobile phases modified with cyclodextrins (under given chromatographic conditions, in which CD additive is strongly eluted by binary organic-water mobile phase, for example acetonitrile:water 35:65 ( v / v ), allow to use the temperature as an effective way to control selectivity in liquid chromatography, similarly to gas chromatography, but using very narrow temperature range [41]. General phenomenological model describing such liquid chromatography retention controlled by supramolecular complexes creation is based on the observation that retention of inclusion complexes can be varied between two lines formed by the Van’t Hoff plot of free cyclodextrin and the Van’t Hoff plot of the uncomplexed solute [15, 42–49].…”

Section: Introductionmentioning

confidence: 99%

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Unexpected differences between planar and column liquid chromatographic retention of 1-acenaphthenol enantiomers controlled by supramolecular interactions involving β-cyclodextrin at subambient temperatures

et al. 2017

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We report the results of experimental work focusing on host-guest supramolecular complex creation between macrocyclic compound (β-cyclodextrin) and 1-acenaphthenol enantiomers (racemic mixture) in liquid phase composed of 35% acetonitrile in water (v/v) at different temperatures ranging from 0 to 90 °C. Experimental setup involved several analytical protocols based on classical non-forced flow planar chromatography (RP-18 TLC plates), micro-TLC (RP-18 W HPTLC plates), column chromatography (HPLC with C-18 and C-30 stationary phases), as well as UV-Vis spectrophotometry and optical microscopy. It has been found that under various planar chromatographic conditions (stationary plates type, chamber shape and volume, development mode, and saturation) non-typical retention properties (extremely high retention) of 1-acenaphthenol at subambient temperatures can be observed. To our knowledge, reported experimental results are in opposition to currently described retention models based on column chromatographic investigation of host-guest complexes (where in case of strong interaction of given analyte with macrocyclic mobile phases additive, which itself is non strongly retarded by stationary phase—close to the retention of dead volume marker, the retention of target compounds is shortened at low temperatures). To explain this TLC phenomenon that may have in our opinion a number of practical applications, especially for selective high throughput separation involving microchromatographic and/or microfluidic devices as well fractionation and extraction protocols (using, e.g., bar extraction systems), several experiments were conducted focusing on (i) acenaphthenol chromatography under different instrumental conditions, (ii) cyclodextrin retention measured as analyte or mobile phase additive, (iii) plate development time under different mobile phases and temperature settings, (iv) various column chromatographic conditions including C-30 and two C-18 stationary phases, (v) UV-Vis spectrophotometry, and (vi) microscopy inspection of precipitated CD-acenaphthenol crystals. Analysis of collected data has revealed that the most probable reasons for TLC retention behavior of 1-acenaphthenol under β-cyclodextrin additive conditions can be associated with (i) solubility changes of created host-guest complex, (ii) kinetics of solid complex precipitation, and (iii) differences in analysis time between planar and column chromatography. Because precipitation phenomenon may have a massive impact on analytes quantification involving macrocycles as the mobile phase additives, our previously reported data concerning a number of low-molecular compounds (mainly steroids and non steroidal endocrine disrupting chemicals) using HPLC methodology based on binary mobile phases without and with β-cyclodextrin and its hydroxypropyl derivative were re-examined and results discussed. Considering these data and the whole data set reported presently, the enhanced model of chromatographic retention driven by host-guest interaction was proposed.Electronic s...

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Section: Resultssupporting

confidence: 81%

Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Unexpected differences between planar and column liquid chromatographic retention of 1-acenaphthenol enantiomers controlled by supramolecular interactions involving β-cyclodextrin at subambient temperatures

et al. 2017

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“…Therefore, the monitoring of these low-molecular mass micropollutants in aquatic environments is of great importance. For that reason, numerous studies have been conducted to develop analytical procedures which are suitable for the quantification of a wide range of steroids in water samples, based on various analytical approaches as well as sample concentration and quantification concepts [10,11,12,13,14,15].…”

Section: Introductionmentioning

confidence: 99%

Analysis of Selected Endocrine Disrupters Fraction Including Bisphenols Extracted from Daily Products, Food Packaging and Treated Wastewater Using Optimized Solid-Phase Extraction and Temperature-Dependent Inclusion Chromatography

Kaleniecka

Zarzycki

2019

Molecules

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The aim of this research is to demonstrate the concept and ability for the fast and preliminary screening of complex food and environmental samples for the presence of endocrine disrupters fractions, consisting of low-molecular mass micropollutants, particularly various bisphenols (A, B, C, E, F, S, Z, AF, AP, BP and FL). The developed analytical protocol for this research requires two main steps: (i) optimized solid phase extraction (SPE) for selective isolation, purification and pre-concentration of target fraction, and (ii) selective temperature-dependent inclusion chromatography for samples analysis via a HPLC-UV-VisDAD system using isocratic elution and internal standard quantification approach. The chromatographic experiment revealed that both β-CD and its hydroxypropyl derivative strongly interact with selected bisphenols. This is in contrast to the steroids and PAHs molecules investigated previously, where a strong interaction with β-cyclodextrin was observed. Integrated areas derived from acquired chromatographic profiles for each individual sample were used as the simple classification variable enabling samples comparison. We demonstrated that the proposed analytical protocol allows for fast estimation of EDC fractions in various daily use products, food and environmental samples. The materials of interest were selected due to the presence in surface water ecosystems of their residues, and finally, in raw wastewater including rice bags, plastic bags, cloths, sanitary towels, fish baits and various plastic foils from food products. Treated sewage water released directly to the environment from a municipal treatment plant (Jamno, Koszalin) was also investigated. It has been demonstrated that a whole range of low-molecular mass compounds, which may be detected using UV-Vis detector, can easily be emitted from various in daily use products. The presence of micropollutants in treated wastewater, water ecosystems and plastic waste utilization via technological wastewater treatment processes must be addressed, especially in terms of microplastic-based pollutants acting as endocrine disrupters. It is hoped that the proposed simple analytical protocol will be useful for fast sample classification or selection prior to advanced targeted analysis involving the more accurate quantification of specific analytes using e.g., mass spectrometry detectors.

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Quantification of Low Molecular Mass Compounds Using Thermostated Planar Chromatography

Zarzycki

2010

High-Performance Thin-Layer Chromatography (HPTLC)

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Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography

Cited by 17 publications

References 28 publications

Unexpected differences between planar and column liquid chromatographic retention of 1-acenaphthenol enantiomers controlled by supramolecular interactions involving β-cyclodextrin at subambient temperatures

Unexpected differences between planar and column liquid chromatographic retention of 1-acenaphthenol enantiomers controlled by supramolecular interactions involving β-cyclodextrin at subambient temperatures

Analysis of Selected Endocrine Disrupters Fraction Including Bisphenols Extracted from Daily Products, Food Packaging and Treated Wastewater Using Optimized Solid-Phase Extraction and Temperature-Dependent Inclusion Chromatography

Quantification of Low Molecular Mass Compounds Using Thermostated Planar Chromatography

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