Amphiphilic hydroxyalkyl cellulose derivatives for amorphous solid dispersion prepared by olefin cross-metathesis

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dc.contributor.authorDong, Yifanen
dc.contributor.authorMosquera-Giraldo, Laura I.en
dc.contributor.authorTroutman, Jacoben
dc.contributor.authorSkogstad, Brittnyen
dc.contributor.authorTaylor, Lynne S.en
dc.contributor.authorEdgar, Kevin J.en
dc.contributor.departmentSustainable Biomaterialsen
dc.contributor.departmentChemistryen
dc.contributor.departmentChemical Engineeringen
dc.contributor.departmentMacromolecules Innovation Instituteen
dc.date.accessioned2017-05-01T06:42:18Zen
dc.date.available2017-05-01T06:42:18Zen
dc.date.issued2016-07-07en
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.en
dc.format.extent4953-4963en
dc.format.mimetypeapplication/pdfen
dc.identifierc6py00960c.pdfen
dc.identifierc6py00960c1.pdfen
dc.identifier.doihttps://doi.org/10.1039/c6py00960cen
dc.identifier.eissn1759-9962en
dc.identifier.issn1759-9954en
dc.identifier.issue30en
dc.identifier.urihttp://hdl.handle.net/10919/77567en
dc.identifier.volume7en
dc.language.isoen_USen
dc.publisherRoyal Society of Chemistryen
dc.relation.ispartofRoyal Society of Chemistry Gold Open Access - 2016en
dc.rightsCreative Commons Attribution-NonCommercial 3.0 Unporteden
dc.rights.holderDong, Yifanen
dc.rights.holderMosquera-Giraldo, Laura I.en
dc.rights.holderTroutman, Jacoben
dc.rights.holderSkogstad, Brittnyen
dc.rights.holderTaylor, Lynne S.en
dc.rights.holderEdgar, Kevin J.en
dc.rights.urihttp://creativecommons.org/licenses/by-nc/3.0/en
dc.titleAmphiphilic hydroxyalkyl cellulose derivatives for amorphous solid dispersion prepared by olefin cross-metathesisen
dc.title.serialPolymer Chemistryen
dc.typeArticle - Refereeden
dc.type.dcmitypeTexten
dc.type.dcmitypeDataseten

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