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Conference Paper: Investigation of Photostability of Curcumin via Cocrystallization with Polyphenols

TitleInvestigation of Photostability of Curcumin via Cocrystallization with Polyphenols
Authors
Issue Date2018
PublisherAmerican Association of Pharmaceutical Scientists.
Citation
American Association of Pharmaceutical Scientists (AAPS) PharmSci 360 Annual Meeting, Washington, DC, 4-7 November 2018 How to Cite?
AbstractPurpose: Photodegradation of drug can provoke changes in chemical stability, giving rise to loss in therapeutic efficacy, which may affect determination of packaging material, storage conditions, and shelf life in product development. Curcumin (CUR), a natural food colorant and flavoring agent, has been demonstrated by numerous studies to possess diverse pharmacological activities such as anti-oxidation, anti-cancer, and anti-inflammatory. However, the clinical enhancement of CUR is restricted by its poor water solubility, bioavailability and chemical stability towards oxygen, light, and alkaline conditions. Cocrystallization has attracted increasing attention as a viable approach to modify physicochemical properties of active pharmaceutical ingredients including solubility, stability and hygroscopicity. In this study, we aimed to study and compare the rates of photodegradation of CUR and a range of novel CUR cocrystals in solution at different concentrations, including four previously reported systems, curcumin-resorcinol (CUR-RES) [1], curcumin-pyrogallol (CUR-PYR) [1], curcumin-hydroxyquinol (CUR-HXQ) [2], and curcumin-phloroglucinol (CUR-PHL) [3] as well as two new synthesized systems, curcumin-pyrocatechol (CUR-CAT) and curcumin-hydroquinone (CUR-HYQ). The orders of photodegradation reaction and half-lives of CUR in different cocrystal systems were also determined. Methods: Six CUR cocrystal systems were prepared by using the method we previously reported [3]. In brief, CUR and coformer were dissolved in acetone in a 1:1 stoichiometric ratio, followed by rapid removal of solvent under vacuum. The resulting solid products were oven-dried and physically characterized to confirm phase purity by powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC), and Fourier transform infrared (FTIR). Pure CUR and six CUR cocrystal powders were dissolved in pure ethanol to prepare stock solutions of CUR at concentrations of 1.2∙10-3 M, 1.2∙10-4 M, and 6∙10-5 M (n=3), followed by irradiated at 366 nm under room temperature. 1 mL of samples were taken out at various time points during exposure (5 h, 1 day, 2 days, 3 days). The extent of CUR degradation was quantified with high-performance liquid chromatography (HPLC) assay and the experimental data was fitted into zero, first, and second order kinetic models to determine the photodegradation kinetics. Results: PXRD patterns of two new synthesized CUR cocrystal systems were shown in Fig. 1, both exhibiting distinct diffraction peaks as follows: CUR-HYQ (2θ=10.6°,11.5°,26.7°,and 27.1°) and CUR-CAT (2θ=10.9°,11.9°,26.9°,and 27.8°). The degradation behaviour of CUR itself and in different cocrystal systems at concentration of 1.2∙10-4 M over a time period up to 72 hours was presented in Fig. 2, revealing the order of CUR residue in each system as follows: CUR-CAT (55.4%) > CUR-RES (52.8%) > CUR-HYQ (48.0%) > CUR (47.0%) > CUR-PHL (42.0%) > CUR-PYR (29.8%) > CUR-HXQ (21.4%). The order of CUR remaining at the other two CUR concentrations also showed similar trends within the cocrystal systems with the lower the CUR concentration in the solution, the faster the photodegradation process. It is worth mentioning that coformers of the three cocrystals which displayed superior photostabilities have only two hydroxyl groups whereas there are three O-H groups in the other coformers. The degradation of CUR and all cocrystal systems followed first order kinetics under the applied illumination conditions with degradation rate constants (k) and half-lives (t1/2) listed in Table 1. Notably, decoloring effect was clearly observed in the solutions since the second day of exposure, which was a good indication of CUR photodegradation. Conclusion: The photodegradation kinetics of pure CUR and CUR cocrystals were studied and compared, showing that cocrystallization could be a promising formulation strategy to alleviate the UV-induced degradation of CUR. The present findings may provide an in depth understanding of cocrystallization in enhancing photostability behaviour of CUR, which can be applied to the product development in pharmaceutical industry. References 1. Sanphui, P., et al., Fast dissolving curcumin cocrystals. Crystal Growth & Design, 2011. 11(9): p. 4135-4145. 2. Sathisaran, I. and S.V. Dalvi, Crystal engineering of curcumin with salicylic acid and hydroxyquinol as coformers. Crystal Growth & Design, 2017. 17(7): p. 3974-3988. 3. Chow, S.F., et al., Kinetic entrapment of a hidden curcumin cocrystal with phloroglucinol. Crystal Growth & Design, 2014. 14(10): p. 5079-5089.
DescriptionPoster Presentation - no. M1430-09-068
Persistent Identifierhttp://hdl.handle.net/10722/265187

 

DC FieldValueLanguage
dc.contributor.authorXu, X-
dc.contributor.authorWong, SN-
dc.contributor.authorWan, KY-
dc.contributor.authorChow, SF-
dc.date.accessioned2018-11-20T02:01:49Z-
dc.date.available2018-11-20T02:01:49Z-
dc.date.issued2018-
dc.identifier.citationAmerican Association of Pharmaceutical Scientists (AAPS) PharmSci 360 Annual Meeting, Washington, DC, 4-7 November 2018-
dc.identifier.urihttp://hdl.handle.net/10722/265187-
dc.descriptionPoster Presentation - no. M1430-09-068-
dc.description.abstractPurpose: Photodegradation of drug can provoke changes in chemical stability, giving rise to loss in therapeutic efficacy, which may affect determination of packaging material, storage conditions, and shelf life in product development. Curcumin (CUR), a natural food colorant and flavoring agent, has been demonstrated by numerous studies to possess diverse pharmacological activities such as anti-oxidation, anti-cancer, and anti-inflammatory. However, the clinical enhancement of CUR is restricted by its poor water solubility, bioavailability and chemical stability towards oxygen, light, and alkaline conditions. Cocrystallization has attracted increasing attention as a viable approach to modify physicochemical properties of active pharmaceutical ingredients including solubility, stability and hygroscopicity. In this study, we aimed to study and compare the rates of photodegradation of CUR and a range of novel CUR cocrystals in solution at different concentrations, including four previously reported systems, curcumin-resorcinol (CUR-RES) [1], curcumin-pyrogallol (CUR-PYR) [1], curcumin-hydroxyquinol (CUR-HXQ) [2], and curcumin-phloroglucinol (CUR-PHL) [3] as well as two new synthesized systems, curcumin-pyrocatechol (CUR-CAT) and curcumin-hydroquinone (CUR-HYQ). The orders of photodegradation reaction and half-lives of CUR in different cocrystal systems were also determined. Methods: Six CUR cocrystal systems were prepared by using the method we previously reported [3]. In brief, CUR and coformer were dissolved in acetone in a 1:1 stoichiometric ratio, followed by rapid removal of solvent under vacuum. The resulting solid products were oven-dried and physically characterized to confirm phase purity by powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC), and Fourier transform infrared (FTIR). Pure CUR and six CUR cocrystal powders were dissolved in pure ethanol to prepare stock solutions of CUR at concentrations of 1.2∙10-3 M, 1.2∙10-4 M, and 6∙10-5 M (n=3), followed by irradiated at 366 nm under room temperature. 1 mL of samples were taken out at various time points during exposure (5 h, 1 day, 2 days, 3 days). The extent of CUR degradation was quantified with high-performance liquid chromatography (HPLC) assay and the experimental data was fitted into zero, first, and second order kinetic models to determine the photodegradation kinetics. Results: PXRD patterns of two new synthesized CUR cocrystal systems were shown in Fig. 1, both exhibiting distinct diffraction peaks as follows: CUR-HYQ (2θ=10.6°,11.5°,26.7°,and 27.1°) and CUR-CAT (2θ=10.9°,11.9°,26.9°,and 27.8°). The degradation behaviour of CUR itself and in different cocrystal systems at concentration of 1.2∙10-4 M over a time period up to 72 hours was presented in Fig. 2, revealing the order of CUR residue in each system as follows: CUR-CAT (55.4%) > CUR-RES (52.8%) > CUR-HYQ (48.0%) > CUR (47.0%) > CUR-PHL (42.0%) > CUR-PYR (29.8%) > CUR-HXQ (21.4%). The order of CUR remaining at the other two CUR concentrations also showed similar trends within the cocrystal systems with the lower the CUR concentration in the solution, the faster the photodegradation process. It is worth mentioning that coformers of the three cocrystals which displayed superior photostabilities have only two hydroxyl groups whereas there are three O-H groups in the other coformers. The degradation of CUR and all cocrystal systems followed first order kinetics under the applied illumination conditions with degradation rate constants (k) and half-lives (t1/2) listed in Table 1. Notably, decoloring effect was clearly observed in the solutions since the second day of exposure, which was a good indication of CUR photodegradation. Conclusion: The photodegradation kinetics of pure CUR and CUR cocrystals were studied and compared, showing that cocrystallization could be a promising formulation strategy to alleviate the UV-induced degradation of CUR. The present findings may provide an in depth understanding of cocrystallization in enhancing photostability behaviour of CUR, which can be applied to the product development in pharmaceutical industry. References 1. Sanphui, P., et al., Fast dissolving curcumin cocrystals. Crystal Growth & Design, 2011. 11(9): p. 4135-4145. 2. Sathisaran, I. and S.V. Dalvi, Crystal engineering of curcumin with salicylic acid and hydroxyquinol as coformers. Crystal Growth & Design, 2017. 17(7): p. 3974-3988. 3. Chow, S.F., et al., Kinetic entrapment of a hidden curcumin cocrystal with phloroglucinol. Crystal Growth & Design, 2014. 14(10): p. 5079-5089.-
dc.languageeng-
dc.publisherAmerican Association of Pharmaceutical Scientists. -
dc.relation.ispartofAAPS PharmSci 360 Annual Meeting-
dc.rightsAAPS PharmSci 360 Annual Meeting. Copyright © American Association of Pharmaceutical Scientists.-
dc.rightsThe original publication is available at www.springerlink.com-
dc.titleInvestigation of Photostability of Curcumin via Cocrystallization with Polyphenols-
dc.typeConference_Paper-
dc.identifier.emailWong, SN: katsnw@HKUCC-COM.hku.hk-
dc.identifier.emailChow, SF: asfchow@hku.hk-
dc.identifier.authorityChow, SF=rp02296-
dc.identifier.hkuros296119-
dc.publisher.placeWashington, DC-

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