Solid-state NMR studies of theophylline co-crystals with dicarboxylic acids
•Three co-crystals of theophylline were studied using solid-state NMR and FT-IR.•The NMR assignments were supported by GIPAW calculations.•The application of ssNMR to analysis of the solid drug forms was described. In this work, three polycrystalline materials containing co-crystals of theophylline...
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| Veröffentlicht in: | Journal of pharmaceutical and biomedical analysis 2014-11, Vol.100, p.322-328 |
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| container_title | Journal of pharmaceutical and biomedical analysis |
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| creator | Pindelska, Edyta Sokal, Agnieszka Szeleszczuk, Lukasz Pisklak, Dariusz Maciej Kolodziejski, Waclaw |
| description | •Three co-crystals of theophylline were studied using solid-state NMR and FT-IR.•The NMR assignments were supported by GIPAW calculations.•The application of ssNMR to analysis of the solid drug forms was described.
In this work, three polycrystalline materials containing co-crystals of theophylline with malonic, maleic, and glutaric acids were studied using 13C, 15N and 1H solid-state NMR and FT-IR spectroscopy. The NMR assignments were supported by gauge including projector augmented waves (GIPAW) calculations of chemical shielding, performed using X-ray determined geometry. The experimental 13C cross polarization/magic angle spinning (CP/MAS) NMR results and the calculated isotropic chemical shifts were in excellent agreement. A rapid and convenient method for theophylline co-crystals crystal structure analysis has been proposed for co-crystals, which are potentially new APIs. |
| doi_str_mv | 10.1016/j.jpba.2014.07.011 |
| format | Article |
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In this work, three polycrystalline materials containing co-crystals of theophylline with malonic, maleic, and glutaric acids were studied using 13C, 15N and 1H solid-state NMR and FT-IR spectroscopy. The NMR assignments were supported by gauge including projector augmented waves (GIPAW) calculations of chemical shielding, performed using X-ray determined geometry. The experimental 13C cross polarization/magic angle spinning (CP/MAS) NMR results and the calculated isotropic chemical shifts were in excellent agreement. A rapid and convenient method for theophylline co-crystals crystal structure analysis has been proposed for co-crystals, which are potentially new APIs.</description><identifier>ISSN: 0731-7085</identifier><identifier>EISSN: 1873-264X</identifier><identifier>DOI: 10.1016/j.jpba.2014.07.011</identifier><identifier>PMID: 25194346</identifier><language>eng</language><publisher>England: Elsevier B.V</publisher><subject>Chemistry, Pharmaceutical ; Co-crystals ; Crystallization ; Crystallography, X-Ray ; Dicarboxylic Acids - chemistry ; GIPAW calculations ; Glutarates - chemistry ; Hydrogen Bonding ; Kinetics ; Magnetic Resonance Spectroscopy ; Maleates - chemistry ; Malonates - chemistry ; Molecular Structure ; Spectroscopy, Fourier Transform Infrared ; ssNMR ; Technology, Pharmaceutical - methods ; Theophylline ; Theophylline - analogs & derivatives ; Theophylline - chemistry</subject><ispartof>Journal of pharmaceutical and biomedical analysis, 2014-11, Vol.100, p.322-328</ispartof><rights>2014 Elsevier B.V.</rights><rights>Copyright © 2014 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-d8b1a98f0ff00fa3ec301a8d0d449930537e0a133ee2223e1e1d443fa8ecc2873</citedby><cites>FETCH-LOGICAL-c356t-d8b1a98f0ff00fa3ec301a8d0d449930537e0a133ee2223e1e1d443fa8ecc2873</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0731708514003409$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25194346$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pindelska, Edyta</creatorcontrib><creatorcontrib>Sokal, Agnieszka</creatorcontrib><creatorcontrib>Szeleszczuk, Lukasz</creatorcontrib><creatorcontrib>Pisklak, Dariusz Maciej</creatorcontrib><creatorcontrib>Kolodziejski, Waclaw</creatorcontrib><title>Solid-state NMR studies of theophylline co-crystals with dicarboxylic acids</title><title>Journal of pharmaceutical and biomedical analysis</title><addtitle>J Pharm Biomed Anal</addtitle><description>•Three co-crystals of theophylline were studied using solid-state NMR and FT-IR.•The NMR assignments were supported by GIPAW calculations.•The application of ssNMR to analysis of the solid drug forms was described.
In this work, three polycrystalline materials containing co-crystals of theophylline with malonic, maleic, and glutaric acids were studied using 13C, 15N and 1H solid-state NMR and FT-IR spectroscopy. The NMR assignments were supported by gauge including projector augmented waves (GIPAW) calculations of chemical shielding, performed using X-ray determined geometry. The experimental 13C cross polarization/magic angle spinning (CP/MAS) NMR results and the calculated isotropic chemical shifts were in excellent agreement. A rapid and convenient method for theophylline co-crystals crystal structure analysis has been proposed for co-crystals, which are potentially new APIs.</description><subject>Chemistry, Pharmaceutical</subject><subject>Co-crystals</subject><subject>Crystallization</subject><subject>Crystallography, X-Ray</subject><subject>Dicarboxylic Acids - chemistry</subject><subject>GIPAW calculations</subject><subject>Glutarates - chemistry</subject><subject>Hydrogen Bonding</subject><subject>Kinetics</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Maleates - chemistry</subject><subject>Malonates - chemistry</subject><subject>Molecular Structure</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><subject>ssNMR</subject><subject>Technology, Pharmaceutical - methods</subject><subject>Theophylline</subject><subject>Theophylline - analogs & derivatives</subject><subject>Theophylline - chemistry</subject><issn>0731-7085</issn><issn>1873-264X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEtLAzEUhYMotlb_gAuZpZsZ703mCW5EfOELfIC7kCZ3aMq0qclU7b83perS1Vnc7x44H2OHCBkClifTbLoYq4wD5hlUGSBusSHWlUh5mb9tsyFUAtMK6mLA9kKYAkCBTb7LBnydIi-H7PbZddakoVc9JQ_3T0nol8ZSSFyb9BNyi8mq6-ycEu1S7VeR60LyaftJYqxWfuy-Vp3VidLWhH2208YzHfzkiL1eXrycX6d3j1c352d3qRZF2aemHqNq6hbaFqBVgrQAVLUBk-dNI6AQFYFCIYg454KQMF5Eq2rSmsd5I3a86V14976k0MuZDZq6Ts3JLYPEoixrDg02EeUbVHsXgqdWLrydKb-SCHItUU7lWqJcS5RQySgxPh399C_HMzJ_L7_WInC6ASiu_LDkZdCW5pqM9aR7aZz9r_8b7gaDFA</recordid><startdate>201411</startdate><enddate>201411</enddate><creator>Pindelska, Edyta</creator><creator>Sokal, Agnieszka</creator><creator>Szeleszczuk, Lukasz</creator><creator>Pisklak, Dariusz Maciej</creator><creator>Kolodziejski, Waclaw</creator><general>Elsevier B.V</general><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>201411</creationdate><title>Solid-state NMR studies of theophylline co-crystals with dicarboxylic acids</title><author>Pindelska, Edyta ; Sokal, Agnieszka ; Szeleszczuk, Lukasz ; Pisklak, Dariusz Maciej ; Kolodziejski, Waclaw</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-d8b1a98f0ff00fa3ec301a8d0d449930537e0a133ee2223e1e1d443fa8ecc2873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Chemistry, Pharmaceutical</topic><topic>Co-crystals</topic><topic>Crystallization</topic><topic>Crystallography, X-Ray</topic><topic>Dicarboxylic Acids - chemistry</topic><topic>GIPAW calculations</topic><topic>Glutarates - chemistry</topic><topic>Hydrogen Bonding</topic><topic>Kinetics</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Maleates - chemistry</topic><topic>Malonates - chemistry</topic><topic>Molecular Structure</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>ssNMR</topic><topic>Technology, Pharmaceutical - methods</topic><topic>Theophylline</topic><topic>Theophylline - analogs & derivatives</topic><topic>Theophylline - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pindelska, Edyta</creatorcontrib><creatorcontrib>Sokal, Agnieszka</creatorcontrib><creatorcontrib>Szeleszczuk, Lukasz</creatorcontrib><creatorcontrib>Pisklak, Dariusz Maciej</creatorcontrib><creatorcontrib>Kolodziejski, Waclaw</creatorcontrib><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>Journal of pharmaceutical and biomedical analysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pindelska, Edyta</au><au>Sokal, Agnieszka</au><au>Szeleszczuk, Lukasz</au><au>Pisklak, Dariusz Maciej</au><au>Kolodziejski, Waclaw</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solid-state NMR studies of theophylline co-crystals with dicarboxylic acids</atitle><jtitle>Journal of pharmaceutical and biomedical analysis</jtitle><addtitle>J Pharm Biomed Anal</addtitle><date>2014-11</date><risdate>2014</risdate><volume>100</volume><spage>322</spage><epage>328</epage><pages>322-328</pages><issn>0731-7085</issn><eissn>1873-264X</eissn><abstract>•Three co-crystals of theophylline were studied using solid-state NMR and FT-IR.•The NMR assignments were supported by GIPAW calculations.•The application of ssNMR to analysis of the solid drug forms was described.
In this work, three polycrystalline materials containing co-crystals of theophylline with malonic, maleic, and glutaric acids were studied using 13C, 15N and 1H solid-state NMR and FT-IR spectroscopy. The NMR assignments were supported by gauge including projector augmented waves (GIPAW) calculations of chemical shielding, performed using X-ray determined geometry. The experimental 13C cross polarization/magic angle spinning (CP/MAS) NMR results and the calculated isotropic chemical shifts were in excellent agreement. A rapid and convenient method for theophylline co-crystals crystal structure analysis has been proposed for co-crystals, which are potentially new APIs.</abstract><cop>England</cop><pub>Elsevier B.V</pub><pmid>25194346</pmid><doi>10.1016/j.jpba.2014.07.011</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0731-7085 |
| ispartof | Journal of pharmaceutical and biomedical analysis, 2014-11, Vol.100, p.322-328 |
| issn | 0731-7085 1873-264X |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Chemistry, Pharmaceutical Co-crystals Crystallization Crystallography, X-Ray Dicarboxylic Acids - chemistry GIPAW calculations Glutarates - chemistry Hydrogen Bonding Kinetics Magnetic Resonance Spectroscopy Maleates - chemistry Malonates - chemistry Molecular Structure Spectroscopy, Fourier Transform Infrared ssNMR Technology, Pharmaceutical - methods Theophylline Theophylline - analogs & derivatives Theophylline - chemistry |
| title | Solid-state NMR studies of theophylline co-crystals with dicarboxylic acids |
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