Unexpected differences between planar and column liquid chromatographic retention of 1-acenaphthenol enantiomers controlled by supramolecular interactions involving β-cyclodextrin at subambient temperatures
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 t...
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| Veröffentlicht in: | Analytical and bioanalytical chemistry 2017-05, Vol.409 (14), p.3695-3706 |
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| creator | Ohta, Hatsuichi Włodarczyk, Elżbieta Piaskowski, Krzysztof Kaleniecka, Aleksandra Lewandowska, Lucyna Baran, Michał J. Wojnicz, Mariusz Jinno, Kiyokatsu Saito, Yoshihiro Zarzycki, Paweł K. |
| description | 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 hav |
| doi_str_mv | 10.1007/s00216-017-0313-y |
| format | Article |
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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.</description><identifier>ISSN: 1618-2642</identifier><identifier>EISSN: 1618-2650</identifier><identifier>DOI: 10.1007/s00216-017-0313-y</identifier><identifier>PMID: 28341988</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Acetonitrile ; Additives ; Analytical Chemistry ; beta-cyclodextrin ; Biochemistry ; Characterization and Evaluation of Materials ; Chemical precipitation ; Chemistry ; Chemistry and Materials Science ; Chromatography ; Column chromatography ; Crystals ; Cyclodextrins ; data collection ; Data processing ; Enantiomers ; Endocrine disruptors ; endocrine-disrupting chemicals ; Food Science ; Fractionation ; High performance liquid chromatography ; Inspection ; Ions ; Laboratory Medicine ; Light microscopy ; Liquid chromatography ; Low temperature ; Microfluidics ; Microscopy ; Monitoring/Environmental Analysis ; Optical microscopy ; Phases ; Plates ; Research Paper ; Retention ; solubility ; Spectrophotometry ; spectroscopy ; Stationary phase ; Steroid hormones ; Steroids ; Strong interactions (field theory) ; Supramolecular compounds ; temperature ; β-Cyclodextrin</subject><ispartof>Analytical and bioanalytical chemistry, 2017-05, Vol.409 (14), p.3695-3706</ispartof><rights>The Author(s) 2017</rights><rights>Analytical and Bioanalytical Chemistry is a copyright of Springer, (2017). All Rights Reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c503t-ea72e23048573006df1f43dacab31d8585eca26fb85beb620e8abd998f905ce13</citedby><cites>FETCH-LOGICAL-c503t-ea72e23048573006df1f43dacab31d8585eca26fb85beb620e8abd998f905ce13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00216-017-0313-y$$EPDF$$P50$$Gspringer$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00216-017-0313-y$$EHTML$$P50$$Gspringer$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28341988$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ohta, Hatsuichi</creatorcontrib><creatorcontrib>Włodarczyk, Elżbieta</creatorcontrib><creatorcontrib>Piaskowski, Krzysztof</creatorcontrib><creatorcontrib>Kaleniecka, Aleksandra</creatorcontrib><creatorcontrib>Lewandowska, Lucyna</creatorcontrib><creatorcontrib>Baran, Michał J.</creatorcontrib><creatorcontrib>Wojnicz, Mariusz</creatorcontrib><creatorcontrib>Jinno, Kiyokatsu</creatorcontrib><creatorcontrib>Saito, Yoshihiro</creatorcontrib><creatorcontrib>Zarzycki, Paweł K.</creatorcontrib><title>Unexpected differences between planar and column liquid chromatographic retention of 1-acenaphthenol enantiomers controlled by supramolecular interactions involving β-cyclodextrin at subambient temperatures</title><title>Analytical and bioanalytical chemistry</title><addtitle>Anal Bioanal Chem</addtitle><addtitle>Anal Bioanal Chem</addtitle><description>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.</description><subject>Acetonitrile</subject><subject>Additives</subject><subject>Analytical Chemistry</subject><subject>beta-cyclodextrin</subject><subject>Biochemistry</subject><subject>Characterization and Evaluation of Materials</subject><subject>Chemical precipitation</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chromatography</subject><subject>Column chromatography</subject><subject>Crystals</subject><subject>Cyclodextrins</subject><subject>data collection</subject><subject>Data processing</subject><subject>Enantiomers</subject><subject>Endocrine disruptors</subject><subject>endocrine-disrupting chemicals</subject><subject>Food Science</subject><subject>Fractionation</subject><subject>High performance liquid chromatography</subject><subject>Inspection</subject><subject>Ions</subject><subject>Laboratory Medicine</subject><subject>Light microscopy</subject><subject>Liquid chromatography</subject><subject>Low temperature</subject><subject>Microfluidics</subject><subject>Microscopy</subject><subject>Monitoring/Environmental Analysis</subject><subject>Optical microscopy</subject><subject>Phases</subject><subject>Plates</subject><subject>Research Paper</subject><subject>Retention</subject><subject>solubility</subject><subject>Spectrophotometry</subject><subject>spectroscopy</subject><subject>Stationary phase</subject><subject>Steroid hormones</subject><subject>Steroids</subject><subject>Strong interactions (field theory)</subject><subject>Supramolecular compounds</subject><subject>temperature</subject><subject>β-Cyclodextrin</subject><issn>1618-2642</issn><issn>1618-2650</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>C6C</sourceid><sourceid>BENPR</sourceid><recordid>eNqFUstu1DAUjRCIlsIHsEGW2LAJ-BE7zgYJVbykSmzo2nKcmxlXjp3aztD5LT6k_SUcTRkVJMTK9-qce47v1amqlwS_JRi37xLGlIgak7bGjLB6_6g6JYLImgqOHx_rhp5Uz1K6wphwScTT6oRK1pBOytPq7tLDzQwmw4AGO44QwRtIqIf8A8Cj2WmvI9J-QCa4ZfLI2evFlm4bw6Rz2EQ9b61BETL4bINHYUSk1gZ8AfIWfHCo1Cs2QUxFxucYnCuG_R6lZY56Cg7M4oqP9RmiNqtOKs0uuJ31G3T7szZ748IANzlaj3Qug72eels8UYZpLlN5iZCeV09G7RK8uH_PqstPH7-ff6kvvn3-ev7hojYcs1yDbilQhhvJW4axGEYyNmzQRveMDJJLDkZTMfaS99ALikHqfug6OXaYGyDsrHp_0J2XfoKhbJujdmqOdtJxr4K26k_E263ahJ3iDRYNEUXgzb1ADNcLpKwmmwy4cm8IS1IUY9y0jHP2XyqRklDRFeVCff0X9Sos0ZdLKNK1hMqOi9WbHFgmhpQijMd_E6zWZKlDslRJllqTpfZl5tXDhY8Tv6NUCPRASAXyG4gPrP-p-gtJNeM0</recordid><startdate>20170501</startdate><enddate>20170501</enddate><creator>Ohta, 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differences between planar and column liquid chromatographic retention of 1-acenaphthenol enantiomers controlled by supramolecular interactions involving β-cyclodextrin at subambient temperatures</title><author>Ohta, Hatsuichi ; Włodarczyk, Elżbieta ; Piaskowski, Krzysztof ; Kaleniecka, Aleksandra ; Lewandowska, Lucyna ; Baran, Michał J. ; Wojnicz, Mariusz ; Jinno, Kiyokatsu ; Saito, Yoshihiro ; Zarzycki, Paweł K.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c503t-ea72e23048573006df1f43dacab31d8585eca26fb85beb620e8abd998f905ce13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acetonitrile</topic><topic>Additives</topic><topic>Analytical Chemistry</topic><topic>beta-cyclodextrin</topic><topic>Biochemistry</topic><topic>Characterization and Evaluation of Materials</topic><topic>Chemical precipitation</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chromatography</topic><topic>Column chromatography</topic><topic>Crystals</topic><topic>Cyclodextrins</topic><topic>data collection</topic><topic>Data processing</topic><topic>Enantiomers</topic><topic>Endocrine disruptors</topic><topic>endocrine-disrupting chemicals</topic><topic>Food Science</topic><topic>Fractionation</topic><topic>High performance liquid chromatography</topic><topic>Inspection</topic><topic>Ions</topic><topic>Laboratory Medicine</topic><topic>Light microscopy</topic><topic>Liquid chromatography</topic><topic>Low temperature</topic><topic>Microfluidics</topic><topic>Microscopy</topic><topic>Monitoring/Environmental Analysis</topic><topic>Optical microscopy</topic><topic>Phases</topic><topic>Plates</topic><topic>Research Paper</topic><topic>Retention</topic><topic>solubility</topic><topic>Spectrophotometry</topic><topic>spectroscopy</topic><topic>Stationary phase</topic><topic>Steroid hormones</topic><topic>Steroids</topic><topic>Strong 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Yoshihiro</au><au>Zarzycki, Paweł K.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Unexpected differences between planar and column liquid chromatographic retention of 1-acenaphthenol enantiomers controlled by supramolecular interactions involving β-cyclodextrin at subambient temperatures</atitle><jtitle>Analytical and bioanalytical chemistry</jtitle><stitle>Anal Bioanal Chem</stitle><addtitle>Anal Bioanal Chem</addtitle><date>2017-05-01</date><risdate>2017</risdate><volume>409</volume><issue>14</issue><spage>3695</spage><epage>3706</epage><pages>3695-3706</pages><issn>1618-2642</issn><eissn>1618-2650</eissn><abstract>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 (
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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.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><pmid>28341988</pmid><doi>10.1007/s00216-017-0313-y</doi><tpages>12</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1618-2642 |
| ispartof | Analytical and bioanalytical chemistry, 2017-05, Vol.409 (14), p.3695-3706 |
| issn | 1618-2642 1618-2650 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_5406416 |
| source | Springer Nature - Complete Springer Journals |
| subjects | Acetonitrile Additives Analytical Chemistry beta-cyclodextrin Biochemistry Characterization and Evaluation of Materials Chemical precipitation Chemistry Chemistry and Materials Science Chromatography Column chromatography Crystals Cyclodextrins data collection Data processing Enantiomers Endocrine disruptors endocrine-disrupting chemicals Food Science Fractionation High performance liquid chromatography Inspection Ions Laboratory Medicine Light microscopy Liquid chromatography Low temperature Microfluidics Microscopy Monitoring/Environmental Analysis Optical microscopy Phases Plates Research Paper Retention solubility Spectrophotometry spectroscopy Stationary phase Steroid hormones Steroids Strong interactions (field theory) Supramolecular compounds temperature β-Cyclodextrin |
| title | Unexpected differences between planar and column liquid chromatographic retention of 1-acenaphthenol enantiomers controlled by supramolecular interactions involving β-cyclodextrin at subambient temperatures |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-10T19%3A37%3A33IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Unexpected%20differences%20between%20planar%20and%20column%20liquid%20chromatographic%20retention%20of%201-acenaphthenol%20enantiomers%20controlled%20by%20supramolecular%20interactions%20involving%20%CE%B2-cyclodextrin%20at%20subambient%20temperatures&rft.jtitle=Analytical%20and%20bioanalytical%20chemistry&rft.au=Ohta,%20Hatsuichi&rft.date=2017-05-01&rft.volume=409&rft.issue=14&rft.spage=3695&rft.epage=3706&rft.pages=3695-3706&rft.issn=1618-2642&rft.eissn=1618-2650&rft_id=info:doi/10.1007/s00216-017-0313-y&rft_dat=%3Cproquest_pubme%3E1881269540%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1971289566&rft_id=info:pmid/28341988&rfr_iscdi=true |