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dc.contributor.authorDong, Yifan
dc.contributor.authorMosquera-Giraldo, Laura I.
dc.contributor.authorTroutman, Jacob
dc.contributor.authorSkogstad, Brittny
dc.contributor.authorTaylor, Lynne S.
dc.contributor.authorEdgar, Kevin J.
dc.date.accessioned2017-05-01T06:42:18Z
dc.date.available2017-05-01T06:42:18Z
dc.date.issued2016-07-07
dc.identifierc6py00960c.pdf
dc.identifierc6py00960c1.pdf
dc.identifier.issn1759-9954
dc.identifier.urihttp://hdl.handle.net/10919/77567
dc.description.abstractOlefin cross-metathesis (CM) has enabled design and synthesis of diverse, amphiphilic cellulose ether derivatives (e.g. of ethyl and methyl cellulose). In this paper, hydroxyalkyl cellulose was selected as a hydrophilic starting material, with the additional advantage that it has DS (OH) 3.0 that allows targeting of a full range of DS of selected functional groups. Hydroxypropyl cellulose (HPC) was first etherified with 5-bromopent-1-ene to attach olefin “handles” for metathesis, whereby control of molar ratios of sodium hydride and 5-bromopent-1-ene permits full DS control of appended olefin. These olefin-terminated HPC ethers then were subjected to CM with acrylic acid and different acrylates, followed by diimide hydrogenation to reduce the resulting α,β-unsaturation. NMR and FT-IR spectroscopies were useful tools for following reaction progress. One of the product carboxyl-functionalized HPC derivatives, designated HPC-Pen106-AA-H, showed high promise as a crystallization inhibitor of the antiviral drug telaprevir. Its nucleation-induction inhibitory ability was compared to those of commercial controls, HPC and HPMCAS. All three polymers were very effective for inhibiting telaprevir crystallization, increasing induction time up to 8-fold. HPC did not effectively prevent amorphous particle growth, whereas the carboxyl-containing HPC-Pen106-AA-H and HPMCAS were able to prevent formation of agglomerates of amorphous drugs.
dc.format.extent4953-4963
dc.format.mimetypeapplication/pdf
dc.language.isoen_US
dc.publisherRoyal Society of Chemistry
dc.relation.ispartofRoyal Society of Chemistry Gold Open Access - 2016
dc.rightsCC BY-NC 3.0
dc.rightsCreative Commons Attribution-NonCommercial 3.0 Unported
dc.rights.urihttps://creativecommons.org/licenses/by-nc/3.0/
dc.titleAmphiphilic hydroxyalkyl cellulose derivatives for amorphous solid dispersion prepared by olefin cross-metathesis
dc.typeArticle
dc.rights.holderDong, Yifan
dc.rights.holderMosquera-Giraldo, Laura I.
dc.rights.holderTroutman, Jacob
dc.rights.holderSkogstad, Brittny
dc.rights.holderTaylor, Lynne S.
dc.rights.holderEdgar, Kevin J.
dc.contributor.departmentVirginia Tech. Department of Sustainable Biomaterials
dc.contributor.departmentVirginia Tech. Department of Chemistry
dc.contributor.departmentVirginia Tech. Department of Chemical Engineering
dc.contributor.departmentVirginia Tech. Macromolecules Innovation Institute
dc.title.serialPolymer Chemistry
dc.identifier.doihttps://doi.org/10.1039/c6py00960c
dc.identifier.volume7
dc.identifier.issue30
dc.type.dcmitypeText
dc.type.dcmitypeDataset
dc.identifier.eissn1759-9962


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License: CC BY-NC 3.0