Supramolecular dynamics of thalidomide and its derivatives in water‐sediment system
Identifieur interne : 000761 ( Istex/Corpus ); précédent : 000760; suivant : 000762Supramolecular dynamics of thalidomide and its derivatives in water‐sediment system
Auteurs : Imran Ali ; Vinod K. Gupta ; Hassan Y. Aboul-EneinSource :
- Chirality [ 0899-0042 ] ; 2010-05-05.
English descriptors
- Teeft :
- Acetonitrile, Adsorption, Chiral, Chiral interconversions, Chiral inversion, Chiral resolution, Chiral separation, Chiral thalidomide, Chirality, Chromatographic parameters, Contact time, Derivative, Dynamic equilibrium, Enantiomer, Equilibrium concentration, Experimental conditions, Freundlich, Freundlich constants, Hplc, Interconversions, Kinetics, Natural conditions, Particle size, Percentage recoveries, Pure thalidomides, Racemic, Rate constants, Resolution factors, Retention times, Riverine, Riverine water, Ruthenium, Sediment, Sediment samples, Sodium magnesium silicate, Solid phase extraction, Spiked water samples, Supramolecular, Supramolecular dynamics, Supramolecular level, Thalidomide, Thalidomide derivatives, Thalidomide enantiomers, Thalidomide table, Zymark turbo.
Abstract
The contamination of drug residues, including chiral ones, is not acceptable in earth's ecosystem. The dynamicity of enantiomers of thalidomide and its derivatives (3‐methyl thalidomide, 3‐ethyl thalidomide, and 3‐butyl thalidomide) was ascertained at supramolecular level in water‐sediment system using solid phase extraction (SPE) and stereoselective HPLC. Enantiomeric separation of these drugs was carried out on Ceramosphere RU‐2 (25 cm × 0.46 cm, particle size 50 μm) chiral column using pure ethanol (1.0 ml/min) as eluent at 230 nm detection. Retention times, capacity, separation, and resolution factors of the enantiomers of these drugs were in the range of 20.0–36.0, 2.08–3.93, 1.35–1.57, and 1.0–2.0 min, respectively. Percentage recoveries of the enantiomers in SPE were in the range of 90.0 to 95.0 in water‐sediment system. Langmuir and Freundlich model were best fitted for dynamic equilibrium concentrations at different experimental parameters. Thalidomide and its derivatives follow first‐order kinetics at dynamic equilibrium. The rate constants of chiral interconversions were 0.390 and 0.385 days−1 for S‐ and R‐enantiomers, respectively. The uptake of thalidomide by sediment is quite good and of endothermic nature indicating good self‐purification capacity of the nature for such toxic species. Chirality, 2010. © 2009 Wiley‐Liss, Inc.
Url:
DOI: 10.1002/chir.20757
Links to Exploration step
ISTEX:AD14EA12F742F376034D043486C189FE7C47C61FLe document en format XML
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The dynamicity of enantiomers of thalidomide and its derivatives (3‐methyl thalidomide, 3‐ethyl thalidomide, and 3‐butyl thalidomide) was ascertained at supramolecular level in water‐sediment system using solid phase extraction (SPE) and stereoselective HPLC. Enantiomeric separation of these drugs was carried out on Ceramosphere RU‐2 (25 cm × 0.46 cm, particle size 50 μm) chiral column using pure ethanol (1.0 ml/min) as eluent at 230 nm detection. Retention times, capacity, separation, and resolution factors of the enantiomers of these drugs were in the range of 20.0–36.0, 2.08–3.93, 1.35–1.57, and 1.0–2.0 min, respectively. Percentage recoveries of the enantiomers in SPE were in the range of 90.0 to 95.0 in water‐sediment system. Langmuir and Freundlich model were best fitted for dynamic equilibrium concentrations at different experimental parameters. Thalidomide and its derivatives follow first‐order kinetics at dynamic equilibrium. The rate constants of chiral interconversions were 0.390 and 0.385 days−1 for S‐ and R‐enantiomers, respectively. The uptake of thalidomide by sediment is quite good and of endothermic nature indicating good self‐purification capacity of the nature for such toxic species. 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The dynamicity of enantiomers of thalidomide and its derivatives (3‐methyl thalidomide, 3‐ethyl thalidomide, and 3‐butyl thalidomide) was ascertained at supramolecular level in water‐sediment system using solid phase extraction (SPE) and stereoselective HPLC. Enantiomeric separation of these drugs was carried out on Ceramosphere RU‐2 (25 cm × 0.46 cm, particle size 50 μm) chiral column using pure ethanol (1.0 ml/min) as eluent at 230 nm detection. Retention times, capacity, separation, and resolution factors of the enantiomers of these drugs were in the range of 20.0–36.0, 2.08–3.93, 1.35–1.57, and 1.0–2.0 min, respectively. Percentage recoveries of the enantiomers in SPE were in the range of 90.0 to 95.0 in water‐sediment system. Langmuir and Freundlich model were best fitted for dynamic equilibrium concentrations at different experimental parameters. Thalidomide and its derivatives follow first‐order kinetics at dynamic equilibrium. 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unit="issue">4</biblScope><biblScope unit="page" from="416">416</biblScope><biblScope unit="page" to="424">424</biblScope><biblScope unit="page-count">9</biblScope><publisher>Wiley Subscription Services, Inc., A Wiley Company</publisher><pubPlace>Hoboken</pubPlace><date type="published" when="2010-05-05"></date></imprint></monogr></biblStruct></sourceDesc></fileDesc><encodingDesc><schemaRef type="ODD" url="https://xml-schema.delivery.istex.fr/tei-istex.odd"></schemaRef><appInfo><application ident="pub2tei" version="1.0.10" when="2019-12-20"><label>pub2TEI-ISTEX</label><desc>A set of style sheets for converting XML documents encoded in various scientific publisher formats into a common TEI format.
<ref target="http://www.tei-c.org/">We use TEI</ref></desc></application></appInfo></encodingDesc><profileDesc><abstract xml:lang="en" style="main"><head>Abstract</head><p>The contamination of drug residues, including chiral ones, is not acceptable in earth's ecosystem. The dynamicity of enantiomers of thalidomide and its derivatives (3‐methyl thalidomide, 3‐ethyl thalidomide, and 3‐butyl thalidomide) was ascertained at supramolecular level in water‐sediment system using solid phase extraction (SPE) and stereoselective HPLC. Enantiomeric separation of these drugs was carried out on Ceramosphere RU‐2 (25 cm × 0.46 cm, particle size 50 μm) chiral column using pure ethanol (1.0 ml/min) as eluent at 230 nm detection. Retention times, capacity, separation, and resolution factors of the enantiomers of these drugs were in the range of 20.0–36.0, 2.08–3.93, 1.35–1.57, and 1.0–2.0 min, respectively. Percentage recoveries of the enantiomers in SPE were in the range of 90.0 to 95.0 in water‐sediment system. Langmuir and Freundlich model were best fitted for dynamic equilibrium concentrations at different experimental parameters. Thalidomide and its derivatives follow first‐order kinetics at dynamic equilibrium. The rate constants of chiral interconversions were 0.390 and 0.385 days<hi rend="superscript">−1</hi> for <hi rend="italic">S</hi>‐ and <hi rend="italic">R</hi>‐enantiomers, respectively. The uptake of thalidomide by sediment is quite good and of endothermic nature indicating good self‐purification capacity of the nature for such toxic species. Chirality, 2010. © 2009 Wiley‐Liss, Inc.</p></abstract><textClass><keywords xml:lang="en"><term xml:id="kwd1">chiral separations</term><term xml:id="kwd2">supramolecular chiral dynamics</term><term xml:id="kwd3">thalidomide</term><term xml:id="kwd4">water‐sediment system</term></keywords><keywords rend="articleCategory"><term>Regular Article</term></keywords><keywords rend="tocHeading1"><term>Regular Articles</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc><revisionDesc><change when="2019-12-20" who="#istex" xml:id="pub2tei">formatting</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-NWBFR51V-2/fulltext.txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" type="serialArticle" xml:lang="en"><header><publicationMeta level="product"><publisherInfo><publisherName>Wiley Subscription Services, Inc., A Wiley Company</publisherName><publisherLoc>Hoboken</publisherLoc></publisherInfo><doi registered="yes">10.1002/(ISSN)1520-636X</doi><issn type="print">0899-0042</issn><issn type="electronic">1520-636X</issn><idGroup><id type="product" value="CHIR"></id></idGroup><titleGroup><title type="main" xml:lang="en" sort="CHIRALITY">Chirality</title><title type="short">Chirality</title></titleGroup></publicationMeta><publicationMeta level="part" position="40"><doi origin="wiley" registered="yes">10.1002/chir.v22:4</doi><numberingGroup><numbering type="journalVolume" number="22">22</numbering><numbering type="journalIssue">4</numbering></numberingGroup><coverDate startDate="2010-05-05">5 May 2010</coverDate></publicationMeta><publicationMeta level="unit" type="article" position="70" status="forIssue"><doi origin="wiley" registered="yes">10.1002/chir.20757</doi><idGroup><id type="unit" value="CHIR20757"></id></idGroup><countGroup><count type="pageTotal" number="9"></count></countGroup><titleGroup><title type="articleCategory">Regular Article</title><title type="tocHeading1">Regular Articles</title></titleGroup><copyright ownership="publisher">Copyright © 2009 Wiley‐Liss, Inc.</copyright><eventGroup><event type="manuscriptReceived" date="2009-02-11"></event><event type="manuscriptAccepted" date="2009-05-27"></event><event type="publishedOnlineEarlyUnpaginated" date="2009-07-17"></event><event type="firstOnline" date="2009-07-17"></event><event type="publishedOnlineFinalForm" date="2010-03-22"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.3.15 mode:FullText source:HeaderRef result:HeaderRef" date="2010-07-21"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-09"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-16"></event></eventGroup><numberingGroup><numbering type="pageFirst">416</numbering><numbering type="pageLast">424</numbering></numberingGroup><correspondenceTo><lineatedText><line>Imran Ali, Department of Chemistry, Jamia Millia Islamia (Central University), New Delhi 110025, India</line><line>Hassan Y. Aboul‐Enein, Pharmaceutical and Medicinal Chemistry Department, National Research Centre, Dokki, Cairo 12311, Egypt</line></lineatedText></correspondenceTo><linkGroup><link type="toTypesetVersion" href="file:CHIR.CHIR20757.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="4"></count><count type="tableTotal" number="7"></count><count type="referenceTotal" number="28"></count><count type="wordTotal" number="797"></count></countGroup><titleGroup><title type="main" xml:lang="en">Supramolecular dynamics of thalidomide and its derivatives in water‐sediment system</title><title type="short" xml:lang="en">Supramolecular Dynamics of Thalidomide</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1" corresponding="yes"><personName><givenNames>Imran</givenNames><familyName>Ali</familyName></personName><contactDetails><email>drimran_ali@yahoo.com</email></contactDetails></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af2 #af3"><personName><givenNames>Vinod K.</givenNames><familyName>Gupta</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af4 #af5" corresponding="yes"><personName><givenNames>Hassan Y.</givenNames><familyName>Aboul‐Enein</familyName></personName><contactDetails><email>enein@gawab.com</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="IN" type="organization"><unparsedAffiliation>Department of Chemistry, Jamia Millia Islamia (Central University), New Delhi, India</unparsedAffiliation></affiliation><affiliation xml:id="af2" countryCode="IN" type="organization"><unparsedAffiliation>Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee ‐ 247667, India</unparsedAffiliation></affiliation><affiliation xml:id="af3" countryCode="SA" type="organization"><unparsedAffiliation>Department of Chemistry, College of Science, King Fahd University of Petroleum and Minerals, Dhahran ‐ 31261, Kingdom of Saudi Arabia</unparsedAffiliation></affiliation><affiliation xml:id="af4" countryCode="EG" type="organization"><unparsedAffiliation>Department of Pharmaceutical and Medicinal Chemistry, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Cairo 12311, Egypt</unparsedAffiliation></affiliation><affiliation xml:id="af5" countryCode="MY" type="organization"><unparsedAffiliation>Department of Chemistry, Universiti Teknologi Malaysia (UTM), Skudai. 81310, Johor Darul Ta'zim, Malaysia</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">chiral separations</keyword><keyword xml:id="kwd2">supramolecular chiral dynamics</keyword><keyword xml:id="kwd3">thalidomide</keyword><keyword xml:id="kwd4">water‐sediment system</keyword></keywordGroup><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>The contamination of drug residues, including chiral ones, is not acceptable in earth's ecosystem. The dynamicity of enantiomers of thalidomide and its derivatives (3‐methyl thalidomide, 3‐ethyl thalidomide, and 3‐butyl thalidomide) was ascertained at supramolecular level in water‐sediment system using solid phase extraction (SPE) and stereoselective HPLC. Enantiomeric separation of these drugs was carried out on Ceramosphere RU‐2 (25 cm × 0.46 cm, particle size 50 μm) chiral column using pure ethanol (1.0 ml/min) as eluent at 230 nm detection. Retention times, capacity, separation, and resolution factors of the enantiomers of these drugs were in the range of 20.0–36.0, 2.08–3.93, 1.35–1.57, and 1.0–2.0 min, respectively. Percentage recoveries of the enantiomers in SPE were in the range of 90.0 to 95.0 in water‐sediment system. Langmuir and Freundlich model were best fitted for dynamic equilibrium concentrations at different experimental parameters. Thalidomide and its derivatives follow first‐order kinetics at dynamic equilibrium. The rate constants of chiral interconversions were 0.390 and 0.385 days<sup>−1</sup> for <i>S</i>‐ and <i>R</i>‐enantiomers, respectively. The uptake of thalidomide by sediment is quite good and of endothermic nature indicating good self‐purification capacity of the nature for such toxic species. Chirality, 2010. © 2009 Wiley‐Liss, Inc.</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Supramolecular dynamics of thalidomide and its derivatives in water‐sediment system</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Supramolecular Dynamics of Thalidomide</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Supramolecular dynamics of thalidomide and its derivatives in water‐sediment system</title></titleInfo><name type="personal"><namePart type="given">Imran</namePart><namePart type="family">Ali</namePart><affiliation>Department of Chemistry, Jamia Millia Islamia (Central University), New Delhi, India</affiliation><affiliation>E-mail: drimran_ali@yahoo.com</affiliation><affiliation>Imran Ali, Department of Chemistry, Jamia Millia Islamia (Central University), New Delhi 110025, IndiaHassan Y. Aboul‐Enein, Pharmaceutical and Medicinal Chemistry Department, National Research Centre, Dokki, Cairo 12311, Egypt</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Vinod K.</namePart><namePart type="family">Gupta</namePart><affiliation>Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee ‐ 247667, India</affiliation><affiliation>Department of Chemistry, College of Science, King Fahd University of Petroleum and Minerals, Dhahran ‐ 31261, Kingdom of Saudi Arabia</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Hassan Y.</namePart><namePart type="family">Aboul‐Enein</namePart><affiliation>Department of Pharmaceutical and Medicinal Chemistry, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Cairo 12311, Egypt</affiliation><affiliation>Department of Chemistry, Universiti Teknologi Malaysia (UTM), Skudai. 81310, Johor Darul Ta'zim, Malaysia</affiliation><affiliation>E-mail: enein@gawab.com</affiliation><affiliation>Imran Ali, Department of Chemistry, Jamia Millia Islamia (Central University), New Delhi 110025, IndiaHassan Y. Aboul‐Enein, Pharmaceutical and Medicinal Chemistry Department, National Research Centre, Dokki, Cairo 12311, Egypt</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>Wiley Subscription Services, Inc., A Wiley Company</publisher><place><placeTerm type="text">Hoboken</placeTerm></place><dateIssued encoding="w3cdtf">2010-05-05</dateIssued><dateCaptured encoding="w3cdtf">2009-02-11</dateCaptured><dateValid encoding="w3cdtf">2009-05-27</dateValid><copyrightDate encoding="w3cdtf">2010</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">4</extent><extent unit="tables">7</extent><extent unit="references">28</extent><extent unit="words">797</extent></physicalDescription><abstract lang="en">The contamination of drug residues, including chiral ones, is not acceptable in earth's ecosystem. The dynamicity of enantiomers of thalidomide and its derivatives (3‐methyl thalidomide, 3‐ethyl thalidomide, and 3‐butyl thalidomide) was ascertained at supramolecular level in water‐sediment system using solid phase extraction (SPE) and stereoselective HPLC. Enantiomeric separation of these drugs was carried out on Ceramosphere RU‐2 (25 cm × 0.46 cm, particle size 50 μm) chiral column using pure ethanol (1.0 ml/min) as eluent at 230 nm detection. Retention times, capacity, separation, and resolution factors of the enantiomers of these drugs were in the range of 20.0–36.0, 2.08–3.93, 1.35–1.57, and 1.0–2.0 min, respectively. Percentage recoveries of the enantiomers in SPE were in the range of 90.0 to 95.0 in water‐sediment system. Langmuir and Freundlich model were best fitted for dynamic equilibrium concentrations at different experimental parameters. Thalidomide and its derivatives follow first‐order kinetics at dynamic equilibrium. The rate constants of chiral interconversions were 0.390 and 0.385 days−1 for S‐ and R‐enantiomers, respectively. The uptake of thalidomide by sediment is quite good and of endothermic nature indicating good self‐purification capacity of the nature for such toxic species. Chirality, 2010. © 2009 Wiley‐Liss, Inc.</abstract><subject lang="en"><genre>keywords</genre><topic>chiral separations</topic><topic>supramolecular chiral dynamics</topic><topic>thalidomide</topic><topic>water‐sediment system</topic></subject><relatedItem type="host"><titleInfo><title>Chirality</title></titleInfo><titleInfo type="abbreviated"><title>Chirality</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><subject><genre>article-category</genre><topic>Regular Article</topic><topic>Regular Articles</topic></subject><identifier type="ISSN">0899-0042</identifier><identifier type="eISSN">1520-636X</identifier><identifier type="DOI">10.1002/(ISSN)1520-636X</identifier><identifier type="PublisherID">CHIR</identifier><part><date>2010</date><detail type="volume"><caption>vol.</caption><number>22</number></detail><detail type="issue"><caption>no.</caption><number>4</number></detail><extent unit="pages"><start>416</start><end>424</end><total>9</total></extent></part></relatedItem><relatedItem type="references" displayLabel="cit1"><titleInfo><title>Thalidomide and congenital abnormalities</title></titleInfo><name type="personal"><namePart type="given">W</namePart><namePart type="family">McBride</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>journal-article</genre><note type="citation/reference">McBride W. 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Electrophoresis 2006; 27: 2999–3006.</note><part><date>2006</date><detail type="volume"><caption>vol.</caption><number>27</number></detail><extent unit="pages"><start>2999</start><end>3006</end></extent></part><relatedItem type="host"><titleInfo><title>Electrophoresis</title></titleInfo><part><date>2006</date><detail type="volume"><caption>vol.</caption><number>27</number></detail><extent unit="pages"><start>2999</start><end>3006</end></extent></part></relatedItem></relatedItem><identifier type="istex">AD14EA12F742F376034D043486C189FE7C47C61F</identifier><identifier type="ark">ark:/67375/WNG-NWBFR51V-2</identifier><identifier type="DOI">10.1002/chir.20757</identifier><identifier type="ArticleID">CHIR20757</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2009 Wiley‐Liss, Inc.</accessCondition><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-L0C46X92-X">wiley</recordContentSource><recordOrigin>Converted from (version ) to MODS version 3.6.</recordOrigin><recordCreationDate encoding="w3cdtf">2019-11-14</recordCreationDate></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-NWBFR51V-2/record.json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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