Increasing the Solubility and Anti-Inflammatory Activity of Curcumin by Cocrystallization
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Keywords:
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Curcumin, Solubility, Anti-Inflammatory, Cocrystals, Isonicotinamide
Abstract
Curcumin (CUR) is a polyphenolic compound that exhibits potent anti-inflammatory activity. However, only a tiny amount of CUR is absorbed during oral administration, which is because CUR is difficult to dissolve in water. The aim of the research was to increase the solubility of CUR through the cocrystallization technique using isonicotinamide coformer (INIC) by solvent evaporation. Cocrystal characterization was carried out using a powder X-ray diffractometer (PXRD), a differential scanning calorimeter (DSC), a Fourier transform infrared spectrometer (FTIR), and a scanning electron microscope (SEM). Solubility was evaluated using the shaking method, while the anti-inflammatory activity test was carried out using the carrageenan induced mouse leg edema method. The resulting CUR-INIC (1:1) cocrystal has a diffractogram with new diffraction peaks of 2theta at 15.00, 16.22, and 22.89◦ compared to the individual diffractograms of CUR and INIC. In the cocrystal, CUR and INIC form intermolecular interactions of hydrogen bonds, resulting in a new solid phase with a melting point of 160.1◦C. The solubility of the CUR-INIC cocrystal in water was 73.1±0.23 ug/mL, which increased 14 times compared to the solubility of initial CUR, which was only 5.05±0.07 ug/mL. The CUR-INIC cocrystal showed a percentage of edema inhibition in mice (5 hours) 130% more potent than that of initial CUR. Therefore, CUR-INIC cocrystals can be used to improve CUR solubility to obtain more excellent anti-inflammatory effects.
References
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Bergström, C. A. and P. Larsson (2018). Computational Prediction of Drug Solubility in Water Based Systems: Qualitative and Quantitative Approaches used in the Current Drug Discovery and Development Setting. International Journal of Pharmaceutics, 540(1-2); 185–193
Chavan, R. B. and N. R. Shastri (2018). Overview of Multicomponent Solid Forms. Journal of Nanotoxicology and Nanomedicine, 3(1); 23–48
Chen, Y., Y. Lu, R. J. Lee, and G. Xiang (2020). Nano Encapsulated Curcumin: and its Potential for Biomedical Applications. International Journal of Nanomedicine, 15; 3099–3120
Docherty, R., K. Pencheva, and Y. A. Abramov (2015). Low Solubility in Drug Development: De Convoluting the Relative Importance of Solvation and Crystal Packing. Journal of Pharmacy and Pharmacology, 67(6); 847–856
Ejarque, D., T. Calvet, M. Font-Bardia, and J. Pons (2021). Cocrystals Based on 4, 4’-Bipyridine: Influence of Crystal Packing on Melting Point. Crystals, 11(2); 191
Fang, L., Y. Xiao, C. Zhang, Z. Gao, S. Wu, J. Gong, and S. Rohani (2021). Intermolecular Interactions and Solubility Behavior of Multicomponent Crystal Forms of 2, 4-D: Design, Structure Analysis, and Solid-State Characterization. CrystEngComm, 23(43); 7615–7627
Ferreira, P. O., F. J. Caires, F. Z. R. de Souza, R. P. Fernandes, and A. C. de Almeida (2022). Screening of Coformers for Quercetin Cocrystals Through Mechanochemical Methods. Eclética Química, 47(1); 64–75
Fischer, F., A. Heidrich, S. Greiser, S. Benemann, K. Rademann, and F. Emmerling (2016). Polymorphism of Mechanochemically Synthesized Cocrystals: A Case Study. Crystal Growth & Design, 16(3); 1701–1707
Gamidi, R. K., M. Ukrainczyk, J. Zeglinski, and Å. C. Rasmuson (2018). Prediction of Solid State Properties of Co-Crystals using Artificial Neural Network Modelling. Crystal Growth & Design, 18; 133–144
Gao, Y., G. Chen, X. Luan, M. Zou, H. Piao, and G. Cheng (2019). Improved Oral Absorption of Poorly Soluble Curcumin Via the Concomitant use of Borneol. AAPS PharmSciTech, 20; 1–10
Granata, G., I. Paterniti, C. Geraci, F. Cunsolo, E. Esposito, M. Cordaro, A. R. Blanco, S. Cuzzocrea, and G. M. Consoli (2017). Potential Eye Drop Based on a Calix [4] Arene Nanoassembly for Curcumin Delivery: Enhanced Drug Solubility, Stability, and Anti-Inflammatory Effect. Molecular Pharmaceutics, 14(5); 1610–1622
Guo, M., X. Sun, J. Chen, and T. Cai (2021). Pharmaceutical Cocrystals: A Review of Preparations, Physicochemical Properties and Applications. Acta Pharmaceutica Sinica B, 11(8); 2537–2564
Guo, W., S. Du, Y. Lin, B. Lu, C. Yang, J. Wang, and Y. Zeng (2018). Structural and Computational Insights Into the Enhanced Solubility of Dipfluzine by Complexation: Salt and Salt-Cocrystal. New Journal of Chemistry, 42(18); 15068–15078
Gupta, A. K., D. Parasar, A. Sagar, V. Choudhary, B. S. Chopra, R. Garg, Ashish, and N. Khatri (2015). Analgesic and Anti-Inflammatory Properties of Gelsolin in Acetic Acid Induced Writhing, Tail Immersion and Carrageenan Induced Paw Adema in Mice. PloS one, 10(8); e0135558
Hakim, L., D. Mardiana, U. Rokhiyah, M. L. A. D. Lestari, and Z. Ningsih (2021). Structure and Dynamics of Curcumin Encapsulated Lecithin Micelles: A Molecular Dynamics Simulation Study. Science and Technology Indonesia, 6(3); 113–120
Haneef, J., S. Ali, and R. Chadha (2021). Emerging Multi-Drug Eutectics: Opportunities and Challenges. AAPS PharmSciTech, 22; 1–17
Haneef, J. and R. Chadha (2017). Drug-Drug Multicomponent Solid Forms: Cocrystal, Coamorphous and Eutectic of Three Poorly Soluble Antihypertensive Drugs using Mechanochemical Approach. AAPS PharmSciTech, 18; 2279–2290
Hanif, M., N. Ameer, Q.-u.-A. Ahmad, M. Aziz, K. Mahmood, N. Ramzan, and H. M. Abdur Rahman (2022). Improved Solubility and Corneal Permeation of PEGylated Curcumin Complex used for the Treatment of Ophthalmic Bacterial Infections. Plos one, 17(4); e0258355
He, Y., H. Liu, W. Bian, Y. Liu, X. Liu, S. Ma, X. Zheng, Z. Du, K. Zhang, and D. Ouyang (2019). Molecular Interactions for the Curcumin-Polymer Complex with Enhanced Anti-Inflammatory Effects. Pharmaceutics, 11(9); 442
Karimi-Jafari, M., L. Padrela, G. M. Walker, and D. M. Croker (2018). Creating Cocrystals: A Review of Pharmaceutical Cocrystal Preparation Routes and Applications. Crystal Growth & Design, 18(10); 6370–6387
Kawano, Y., S. Chen, and T. Hanawa (2021). Solubility Enhancement of Ibuprofen by Adsorption onto Spherical Porous Calcium Silicate. Pharmaceutics, 13(6); 767
Kerr, H. E., L. K. Softley, K. Suresh, A. Nangia, P. Hodgkinson, and I. R. Evans (2015). A Furosemide–Isonicotinamide Cocrystal: An Investigation of Properties and Extensive Structural Disorder. CrystEngComm, 17(35); 6707–6715
Ketkar, S., S. K. Pagire, N. R. Goud, K. Mahadik, A. Nangia, and A. Paradkar (2016). Tracing the Architecture of Caffeic Acid Phenethyl Ester Cocrystals: Studies on Crystal Structure, Solubility, and Bioavailability Implications. Crystal Growth & Design, 16(10); 5710–5716
Khames, A. (2017). Investigation of the Effect of Solubility Increase at the Main Absorption Site on Bioavailability of BCS Class II Drug (Risperidone) using Liquisolid Technique. Drug Delivery, 24(1); 328–338
Kilinkissa, O. E., K. K. Govender, and N. B. Báthori (2020). Melting Point–Solubility–Structure Correlations in Chiral and Racemic Model Cocrystals. CrystEngComm, 22(16); 2766–2771
Kuleshova, L., D. Hofmann, and R. Boese (2013). Lattice Energy Calculation–a Quick Tool for Screening of Cocrystals and Estimation of Relative Solubility. Case of Flavonoids. Chemical Physics Letters, 564; 26–32
Liu, H., H. Lin, Z. Zhou, and L. Li (2021). Bergenin-Isonicotinamide (1:1) Cocrystal with Enhanced Solubility and Investigation of its Solubility Behavior. Journal of Drug Delivery Science and Technology, 64; 102556
Ma, X. Q., C. Zhuang, B. C. Wang, Y. F. Huang, Q. Chen, and N. Lin (2019). Cocrystal of Apigenin with Higher Solubility, Enhanced Oral Bioavailability, and Anti-Inflammatory Effect. Crystal Growth & Design, 19(10); 5531–5537
Maheshwari, C., A. Jayasankar, N. A. Khan, G. E. Amidon, and N. Rodríguez-Hornedo (2009). Factors that Influence the Spontaneous Formation of Pharmaceutical Cocrystals by Simply Mixing Solid Reactants. CrystEngComm, 11(3); 493–500
Ozaki, S., Y. Nakagawa, O. Shirai, and K. Kano (2014). Substituent Effect on the Thermodynamic Solubility of Structural Analogs: Relative Contribution of Crystal Packing and Hydration. Journal of Pharmaceutical Sciences, 103(11); 3524–3531
Palanisamy, V., P. Sanphui, M. Prakash, and V. Chernyshev (2019). Multicomponent Solid Forms of the Uric Acid Reabsorption Inhibitor Lesinurad and Cocrystal Polymorphs with Urea: DFT Simulation and Solubility Study. Acta Crystallographica Section C: Structural Chemistry, 75(8); 1102–1117
Pantwalawalkar, J., H. More, D. Bhange, U. Patil, and N. Jadhav (2021). Novel Curcumin Ascorbic Acid Cocrystal for Improved Solubility. Journal of Drug Delivery Science and Technology, 61; 102233
Paulazzi, A. R., B. O. Alves, G. A. Zilli, A. E. Dos Santos, F. Petry, K. D. Soares, L. J. Danielli, J. Pedroso, M. A. Apel, and G. P. S. Aguiar (2022). Curcumin and n-Acetylcysteine Cocrystal Produced with Supercritical Solvent: Characterization, Solubility, and Preclinical Evaluation of Antinociceptive and Anti-Inflammatory Activities. Inflammopharmacology, 30(1); 327–341
Peng, Y., M. Ao, B. Dong, Y. Jiang, L. Yu, Z. Chen, C. Hu, and R. Xu (2021). Anti-Inflammatory Effects of Curcumin in the Inflammatory Diseases: Status, Limitations and Counter-measures. Drug Design, Development and Therapy; 4503–4525
Priyadarsini, K. I. (2014). The Chemistry of Curcumin: From Extraction to Therapeutic Agent. Molecules, 19(12); 20091–20112
Qiao, N., M. Li, W. Schlindwein, N. Malek, A. Davies, and G. Trappitt (2011). Pharmaceutical Cocrystals: An Overview. International Journal of Pharmaceutics, 419(1-2); 1–11
Salahinejad, M., T. C. Le, and D. A. Winkler (2013). Capturing the Crystal: Prediction of Enthalpy of Sublimation, Crystal Lattice Energy, and Melting Points of Organic Compounds. Journal of Chemical Information and Modeling, 53(1); 223–229
Sanphui, P. and G. Bolla (2018). Curcumin, a Biological Wonder Molecule: A Crystal Engineering Point of View. Crystal Growth & Design, 18(9); 5690–5711
Sanphui, P., N. R. Goud, U. R. Khandavilli, S. Bhanoth, and A. Nangia (2011). New Polymorphs of Curcumin. Chemical Communications, 47(17); 5013–5015
Satapathy, B. S., A. Patel, R. N. Sahoo, and S. Mallick (2021). Crystal Products of Lamotrigine Citric Acid for Improvement of in Vitro Drug Release in Simulated Gastric Fluid. Journal of the Serbian Chemical Society, 86(1); 51–61
Sharma, M., B. S. Inbaraj, P. K. Dikkala, K. Sridhar, A. N. Mude, and K. Narsaiah (2022). Preparation of Curcumin Hydrogel Beads for the Development of Functional Kulfi: A Tailoring Delivery System. Foods, 11(2); 182
Sohn, S.-I., A. Priya, B. Balasubramaniam, P. Muthuramalingam, C. Sivasankar, A. Selvaraj, A. Valliammai, R. Jothi, and S. Pandian (2021). Biomedical Applications and Bioavailability of Curcumin—An Updated Overview. Pharmaceutics, 13(12); 2102
Suresh, K. and A. Nangia (2018). Curcumin: Pharmaceutical Solids as a Platform to Improve Solubility and Bioavailability. CrystEngComm, 20(24); 3277–3296
Tabanelli, R., S. Brogi, and V. Calderone (2021). Improving Curcumin Bioavailability: Current Strategies and Future Perspectives. Pharmaceutics, 13(10); 1715
Taylor, C. R. and G. M. Day (2018). Evaluating the Energetic Driving Force for Cocrystal Formation. Crystal Growth & Design, 18(2); 892–904
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Authors
Wicaksono, Y., Barikah, . K. Z. ., Yudatama, A. D. ., Maulia, H. ., Nuri, & Setyawan, D. . (2023). Increasing the Solubility and Anti-Inflammatory Activity of Curcumin by Cocrystallization. Science and Technology Indonesia, 8(3), 501–508. https://doi.org/10.26554/sti.2023.8.3.501-508
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