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Evaluation of the taste-masking effects of (2-hydroxypropyl)-β-cyclodextrin on ranitidine hydrochloride; a combined biosensor, spectroscopic and molecular modelling assessment

Chay, SK; Keating, AV; James, C; Aliev, A; Haider, S; Craig, DQM; (2018) Evaluation of the taste-masking effects of (2-hydroxypropyl)-β-cyclodextrin on ranitidine hydrochloride; a combined biosensor, spectroscopic and molecular modelling assessment. RSC Advances (8) pp. 3564-3573. 10.1039/C7RA11015D. Green open access

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Abstract

Taste assessment in an increasingly important aspect of formulation development, particularly for paediatric medications. Electronic taste sensing systems have the potential to offer a rapid, objective and safe method of taste assessment prior to the use of more costly human panels or animal models. In this study, the ability of the TS-5000Z taste sensing system to assess the taste masking efficiency of (2-hydroxypropyl)-β-cyclodextrin (HP-β-CyD) complexes with ranitidine hydrochloride was evaluated in order to explore the potential of the biosensor approach as a means of assessing taste masking by inclusion complexation. Nuclear magnetic resonance (NMR) spectroscopy and molecular docking studies were employed to identify and examine the interaction between ranitidine hydrochloride and HP-β-CyD. Taste-masking efficiencies were determined by the Euclidean distance between taste-masked formulations and the pure drug substance on a PCA score plot. The results showed that with increasing molarity of HP-β-CyD in the formulation, the distance from ranitidine hydrochloride increased, thus indicating a significant difference between the taste of the formulation and that of the pure drug. NMR studies also provided strong supporting evidence for the complexation between HP-β-CyD and ranitidine hydrochloride, with the H3′ region of the former identified as the most likely binding site for the drug. Molecular docking studies suggested that the dimethylamino and diamine groups of the drug form direct hydrogen bonds with the hydroxyl oxygen atoms of HP-β-CyD, while the furan ring docks in close proximity to H3′. This study has demonstrated that the biosensor system may provide quantitative data to assess bitterness of inclusion complexes with HP-β-CyD, while spectroscopic and modelling studies may provide a mechanistic explanation for the taste masking process. This in turn suggests that there is a role for biosensor approaches in providing early screening for taste masking using inclusion complexation and that the combination with mechanistic studies may provide insights into the molecular basis of taste and taste masking.

Type: Article
Title: Evaluation of the taste-masking effects of (2-hydroxypropyl)-β-cyclodextrin on ranitidine hydrochloride; a combined biosensor, spectroscopic and molecular modelling assessment
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/C7RA11015D
Publisher version: http://doi.org/10.1039/C7RA11015D
Language: English
Additional information: © The Royal Society of Chemistry 2018. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (https://creativecommons.org/licenses/by/3.0/).
Keywords: Paediatric medications, Taste assessment, TS-5000Z taste sensing system, Taste masking efficiency of (2-hydroxypropyl)-β-cyclodextrin (HP-β-CyD) complexes, Nuclear magnetic resonance (NMR), Euclidean distance
UCL classification: UCL
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharmaceutics
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10041733
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