Cocrystals and a salt of the bioactive flavonoid: naringenin

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dc.contributor.author Khandavilli, Udaya Bhaskara Rao
dc.contributor.author Skořepová, Eliška
dc.contributor.author Sinha, Abhijeet S.
dc.contributor.author Bhogala, Balakrishna R.
dc.contributor.author Maguire, Nuala M.
dc.contributor.author Maguire, Anita R.
dc.contributor.author Lawrence, Simon E.
dc.date.accessioned 2018-07-10T08:45:12Z
dc.date.available 2018-07-10T08:45:12Z
dc.date.issued 2018-07-03
dc.identifier.citation Khandavilli, U. B. R., Skořepová, E., Sinha, A. S., Bhogala, B. R., Maguire, N. M., Maguire, A. R. and Lawrence, S. E. (2018) 'Cocrystals and a salt of the bioactive flavonoid: naringenin', Crystal Growth and Design. doi:10.1021/acs.cgd.8b00557 en
dc.identifier.issn 1528-7483
dc.identifier.issn 1528-7505
dc.identifier.uri http://hdl.handle.net/10468/6441
dc.identifier.doi 10.1021/acs.cgd.8b00557
dc.description.abstract Cocrystallization studies on Naringenin with 27 coformers have led to the formation of five new solid forms: a piperazinium salt (PIP+-NR-) and four cocrystals with the coformers flavone (FLV), 4-hydroxypyridine (4-HP), anthranilamide (ATA), and 4,4′-bipyridine (Bipy). Structural characterization reveals that the hydrogen bonded head to tail dimer motif in naringenin is maintained only in the cocrystal with flavone (NR-FLV). All four neutral cocrystals maintain the S(6) OH···O=C intramolecular hydrogen bond seen in naringenin with this carbonyl oxygen atom bifurcated. The piperazinium salt is the only structure in which the ether oxygen is involved in hydrogen bonding. Some of the structures display disorder in the chiral center of naringenin, making them anomalous racemic solid solutions. The solubility study revealed that the salt formation has significantly enhanced the solubility of naringenin, for example the piperazinium salt has enhanced solubility of >3,000 times that of the neutral parent compound. en
dc.description.sponsorship Science Foundation Ireland (05/PICA/B802/EC07); Grantová Agentura České Republiky (Grant No. 17-23196S) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher American Chemical Society en
dc.rights © 2018, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth and Design, © American Chemical Society, after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.cgd.8b00557 en
dc.subject Solubility en
dc.subject Naringenin en
dc.subject Piperazinium salt en
dc.title Cocrystals and a salt of the bioactive flavonoid: naringenin en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Simon Lawrence, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: simon.lawrence@ucc.ie en
dc.internal.availability Full text available en
dc.check.info Access to this article is restricted until 12 months after publication by request of the publisher. en
dc.check.date 2019-07-03
dc.date.updated 2018-07-10T08:29:33Z
dc.description.version Accepted Version en
dc.internal.rssid 444828216
dc.internal.rssid 444828232
dc.contributor.funder Science Foundation Ireland en
dc.contributor.funder Grantová Agentura České Republiky en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Crystal Growth and Design en
dc.internal.copyrightchecked Yes en
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress simon.lawrence@ucc.ie en
dc.internal.bibliocheck In press. Check for vol. / issue / page numbers. Amend citation as necessary.
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ en


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