Binding, Molecular Mechanics, and Thermodynamics of Cyclodextrin Inclusion Complexes with Ketoprofen in Aqueous Medium
ABSTRACT The purpose of this work was to study the interaction forces involved in the inclusion processes of ketoprofen with several cyclodextrins and to assess the best cyclodextrin for complexing this antiinflammatory drug. The behavior of the inclusion complexes of ketoprofen with α-, β-, and γ-c...
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| Veröffentlicht in: | Pharmaceutical development and technology 1998, Vol.3 (3), p.307-313 |
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| creator | Díaz, David Escobar Llanos, Carolina Marta Bernad, María Josefa Mora, Jes s Gracia |
| description | ABSTRACT
The purpose of this work was to study the interaction forces involved in the inclusion processes of ketoprofen with several cyclodextrins and to assess the best cyclodextrin for complexing this antiinflammatory drug. The behavior of the inclusion complexes of ketoprofen with α-, β-, and γ-cyclodextrins was studied by UV-VIS direct spectroscopy, 'H NMR, and molecular mechanics. Thermodynamic parameters for the binding processes were obtained from the temperature variations in binding constants, which manifest that "nonclassical" hydrophobic interactions are the main forces involved in these inclusion processes. Binding constants show that β- and γ-cyclodextrins form more stable 1:1 complexes with ketoprofen than does a-cyclodextrin. 1H NMR spectra show that the inclusion degree depends on the size of the internal diameter of cyclodextrin. The geometries calculated on the bases of molecular mechanics for these three-dimensional models indicate high stability. |
| doi_str_mv | 10.3109/10837459809009858 |
| format | Article |
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The purpose of this work was to study the interaction forces involved in the inclusion processes of ketoprofen with several cyclodextrins and to assess the best cyclodextrin for complexing this antiinflammatory drug. The behavior of the inclusion complexes of ketoprofen with α-, β-, and γ-cyclodextrins was studied by UV-VIS direct spectroscopy, 'H NMR, and molecular mechanics. Thermodynamic parameters for the binding processes were obtained from the temperature variations in binding constants, which manifest that "nonclassical" hydrophobic interactions are the main forces involved in these inclusion processes. Binding constants show that β- and γ-cyclodextrins form more stable 1:1 complexes with ketoprofen than does a-cyclodextrin. 1H NMR spectra show that the inclusion degree depends on the size of the internal diameter of cyclodextrin. The geometries calculated on the bases of molecular mechanics for these three-dimensional models indicate high stability.</description><identifier>ISSN: 1083-7450</identifier><identifier>EISSN: 1097-9867</identifier><identifier>DOI: 10.3109/10837459809009858</identifier><identifier>PMID: 9742551</identifier><language>eng</language><publisher>New York, NY: Informa UK Ltd</publisher><subject>Anti-Inflammatory Agents, Non-Steroidal - administration & dosage ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Cyclodextrins - administration & dosage ; Direct spectroscopy ; General pharmacology ; Inclusion complexes with cyclodextrins ; Ketoprofen ; Ketoprofen - administration & dosage ; Ketoprofen - chemistry ; Magnetic Resonance Spectroscopy ; Medical sciences ; Molecular mechanics ; Nuclear magnetic resonance ; Pharmaceutical technology. Pharmaceutical industry ; Pharmacology. Drug treatments ; Spectrophotometry, Ultraviolet ; Thermodynamics</subject><ispartof>Pharmaceutical development and technology, 1998, Vol.3 (3), p.307-313</ispartof><rights>1998 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted 1998</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c345t-143c13f3a7665c27d5459ed50e585d51eb3a5c617a898d5a84aa5795e5faffad3</citedby><cites>FETCH-LOGICAL-c345t-143c13f3a7665c27d5459ed50e585d51eb3a5c617a898d5a84aa5795e5faffad3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.3109/10837459809009858$$EPDF$$P50$$Ginformahealthcare$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.3109/10837459809009858$$EHTML$$P50$$Ginformahealthcare$$H</linktohtml><link.rule.ids>314,780,784,4024,27923,27924,27925,59647,59753,60436,60542,61221,61256,61402,61437</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2413047$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9742551$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Díaz, David</creatorcontrib><creatorcontrib>Escobar Llanos, Carolina Marta</creatorcontrib><creatorcontrib>Bernad, María Josefa</creatorcontrib><creatorcontrib>Mora, Jes s Gracia</creatorcontrib><title>Binding, Molecular Mechanics, and Thermodynamics of Cyclodextrin Inclusion Complexes with Ketoprofen in Aqueous Medium</title><title>Pharmaceutical development and technology</title><addtitle>Pharm Dev Technol</addtitle><description>ABSTRACT
The purpose of this work was to study the interaction forces involved in the inclusion processes of ketoprofen with several cyclodextrins and to assess the best cyclodextrin for complexing this antiinflammatory drug. The behavior of the inclusion complexes of ketoprofen with α-, β-, and γ-cyclodextrins was studied by UV-VIS direct spectroscopy, 'H NMR, and molecular mechanics. Thermodynamic parameters for the binding processes were obtained from the temperature variations in binding constants, which manifest that "nonclassical" hydrophobic interactions are the main forces involved in these inclusion processes. Binding constants show that β- and γ-cyclodextrins form more stable 1:1 complexes with ketoprofen than does a-cyclodextrin. 1H NMR spectra show that the inclusion degree depends on the size of the internal diameter of cyclodextrin. The geometries calculated on the bases of molecular mechanics for these three-dimensional models indicate high stability.</description><subject>Anti-Inflammatory Agents, Non-Steroidal - administration & dosage</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Cyclodextrins - administration & dosage</subject><subject>Direct spectroscopy</subject><subject>General pharmacology</subject><subject>Inclusion complexes with cyclodextrins</subject><subject>Ketoprofen</subject><subject>Ketoprofen - administration & dosage</subject><subject>Ketoprofen - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Molecular mechanics</subject><subject>Nuclear magnetic resonance</subject><subject>Pharmaceutical technology. Pharmaceutical industry</subject><subject>Pharmacology. Drug treatments</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Thermodynamics</subject><issn>1083-7450</issn><issn>1097-9867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE9v1DAQxSMEKqXwATgg-YA4NWCv49gWXMqKPxWtuJRzNLXHxJVjL3ZCu98er3aphJB6sjXze09vXtO8ZPQtZ1S_Y1Rx2QmtqKZUK6EeNcd1Llutevl491e8rQB92jwr5YZSpjQVR82Rlt1KCHbc_P7oo_Xx5ym5TAHNEiCTSzQjRG_KKYFoydWIeUp2G2GqM5IcWW9NSBbv5uwjOY8mLMWnSNZp2gS8w0Ju_TySbzinTU4OI6nY2a8F01KqufXL9Lx54iAUfHF4T5ofnz9drb-2F9-_nK_PLlrDOzG3rOOGccdB9r0wK2lFPRatoCiUsILhNQdheiZBaWUFqA5ASC1QOHAOLD9p3ux9a5AaoMzD5IvBECDu0gyS61Uvuq6CbA-anErJ6IZN9hPk7cDosOt6-K_rqnl1MF-uJ7T3ikO5df_6sIdiILgM0fhyj606xmknK_Zhj_noUp7gNuVghxm2IeW_Gv5Qivf_yEeEMI8GMg43acmx1vvADX8Aa7ytYg</recordid><startdate>1998</startdate><enddate>1998</enddate><creator>Díaz, David</creator><creator>Escobar Llanos, Carolina Marta</creator><creator>Bernad, María Josefa</creator><creator>Mora, Jes s Gracia</creator><general>Informa UK Ltd</general><general>Taylor & Francis</general><general>Informa Healthcare</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>1998</creationdate><title>Binding, Molecular Mechanics, and Thermodynamics of Cyclodextrin Inclusion Complexes with Ketoprofen in Aqueous Medium</title><author>Díaz, David ; Escobar Llanos, Carolina Marta ; Bernad, María Josefa ; Mora, Jes s Gracia</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c345t-143c13f3a7665c27d5459ed50e585d51eb3a5c617a898d5a84aa5795e5faffad3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>Anti-Inflammatory Agents, Non-Steroidal - administration & dosage</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Cyclodextrins - administration & dosage</topic><topic>Direct spectroscopy</topic><topic>General pharmacology</topic><topic>Inclusion complexes with cyclodextrins</topic><topic>Ketoprofen</topic><topic>Ketoprofen - administration & dosage</topic><topic>Ketoprofen - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Molecular mechanics</topic><topic>Nuclear magnetic resonance</topic><topic>Pharmaceutical technology. Pharmaceutical industry</topic><topic>Pharmacology. Drug treatments</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Díaz, David</creatorcontrib><creatorcontrib>Escobar Llanos, Carolina Marta</creatorcontrib><creatorcontrib>Bernad, María Josefa</creatorcontrib><creatorcontrib>Mora, Jes s Gracia</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Pharmaceutical development and technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Díaz, David</au><au>Escobar Llanos, Carolina Marta</au><au>Bernad, María Josefa</au><au>Mora, Jes s Gracia</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Binding, Molecular Mechanics, and Thermodynamics of Cyclodextrin Inclusion Complexes with Ketoprofen in Aqueous Medium</atitle><jtitle>Pharmaceutical development and technology</jtitle><addtitle>Pharm Dev Technol</addtitle><date>1998</date><risdate>1998</risdate><volume>3</volume><issue>3</issue><spage>307</spage><epage>313</epage><pages>307-313</pages><issn>1083-7450</issn><eissn>1097-9867</eissn><abstract>ABSTRACT
The purpose of this work was to study the interaction forces involved in the inclusion processes of ketoprofen with several cyclodextrins and to assess the best cyclodextrin for complexing this antiinflammatory drug. The behavior of the inclusion complexes of ketoprofen with α-, β-, and γ-cyclodextrins was studied by UV-VIS direct spectroscopy, 'H NMR, and molecular mechanics. Thermodynamic parameters for the binding processes were obtained from the temperature variations in binding constants, which manifest that "nonclassical" hydrophobic interactions are the main forces involved in these inclusion processes. Binding constants show that β- and γ-cyclodextrins form more stable 1:1 complexes with ketoprofen than does a-cyclodextrin. 1H NMR spectra show that the inclusion degree depends on the size of the internal diameter of cyclodextrin. The geometries calculated on the bases of molecular mechanics for these three-dimensional models indicate high stability.</abstract><cop>New York, NY</cop><pub>Informa UK Ltd</pub><pmid>9742551</pmid><doi>10.3109/10837459809009858</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1083-7450 |
| ispartof | Pharmaceutical development and technology, 1998, Vol.3 (3), p.307-313 |
| issn | 1083-7450 1097-9867 |
| language | eng |
| recordid | cdi_pubmed_primary_9742551 |
| source | MEDLINE; Taylor & Francis Medical Library - CRKN; Taylor & Francis Journals Complete |
| subjects | Anti-Inflammatory Agents, Non-Steroidal - administration & dosage Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Cyclodextrins - administration & dosage Direct spectroscopy General pharmacology Inclusion complexes with cyclodextrins Ketoprofen Ketoprofen - administration & dosage Ketoprofen - chemistry Magnetic Resonance Spectroscopy Medical sciences Molecular mechanics Nuclear magnetic resonance Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Spectrophotometry, Ultraviolet Thermodynamics |
| title | Binding, Molecular Mechanics, and Thermodynamics of Cyclodextrin Inclusion Complexes with Ketoprofen in Aqueous Medium |
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