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    Mechanism of hydrogen-bonded complex formation between ibuprofen and nanocrystalline hydroxyapatite

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    Publication date
    2017
    Author
    Ryabenkova, Yulia
    Jadav, Niten B.
    Conte, M.
    Hippler, M.F.A.
    Reeves-McLaren, N.
    Coates, Philip D.
    Twigg, Peter C.
    Paradkar, Anant R.
    Keyword
    Hydrogen bonding; Mechanistic studies; Ibuprofen; Hydroxyapatite; Drug delivery; Dissolution
    Rights
    © 2017 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
    Peer-Reviewed
    Yes
    
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    Abstract
    Nanocrystalline hydroxyapatite (nanoHA) is the main hard component of bone and has potential to be used to promote osseointegration of implants and to treat bone defects. Here, using active pharmaceutical ingredients (APIs) like ibuprofen, we report on the prospects of combining nanoHA with biologically active compounds to improve the clinical performance of these treatments. In this study we designed and investigated the possibility of API attachment to the surface of nano-HA crystals via the formation of a hydrogen-bonded complex. The mechanistic studies of an ibuprofen/nanoHA complex formation have been performed using a holistic approach encompassing spectroscopic (FT-IR and Raman) and X-ray diffraction techniques as well as quantum chemistry calculations (DFT), while comparing the behaviour of the ibuprofen/nanoHA complex with that of a physical mixture of the two components. Whereas ibuprofen exists in dimeric form both in solid and liquid state, our study showed that the formation of the ibuprofen/nanoHA complex most likely occurs via the dissociation of the ibuprofen dimer into monomeric species promoted by ethanol, with subsequent attachment of a monomer to the HA surface. An adsorption mode for this process is proposed; this includes hydrogen bonding of the hydroxyl group of ibuprofen to the hydroxyl group of the apatite, together with the interaction of the ibuprofen carbonyl group to an HA calcium centre. Overall, this mechanistic study provides new insights into the molecular interactions between APIs and the surfaces of bioactive inorganic solids and sheds light on the relation between the non-covalent bonding and drug release properties.
    URI
    http://hdl.handle.net/10454/11614
    Version
    Published version
    Citation
    Ryabenkova Y, Jadav N, Conte M et al (2017) Mechanism of hydrogen-bonded complex formation between ibuprofen and nanocrystalline hydroxyapatite. Langmuir. 33(12): 2965-2976.
    Link to publisher’s version
    http://dx.doi.org/10.1021/acs.langmuir.6b04510
    Type
    Article
    Collections
    Life Sciences Publications

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