Regularities of Encapsulation of Tolfenamic Acid and Some Other Non-Steroidal Anti-Inflammatory Drugs in Metal-Organic Framework Based on γ-Cyclodextrin

Overview

Journal Pharmaceutics

Publisher MDPI

Date 2023 Jan 21

PMID 36678700

Authors

Ekaterina Delyagina

Anna Garibyan

Mikhail Agafonov

Irina Terekhova

Affiliations

Soon will be listed here.

Abstract

Metal-organic frameworks based on cyclodextrins (CDs) have been proposed as promising drug delivery systems due to their large surface area, variable pore size, and biocompatibility. In the current work, we investigated an incorporation of tolfenamic acid (TA), a representative of non-steroidal anti-inflammatory drugs (NSAIDs), in a metal-organic framework based on γ-cyclodextrin and potassium cations (γCD-MOF). Composites γCD-MOF/TA obtained by absorption and co-crystallization methods were characterized using powder X-ray diffraction, low temperature nitrogen adsorption/desorption, scanning electron microscopy, and FTIR spectroscopy. It was demonstrated that TA loaded in γCD-MOF has an improved dissolution profile. However, the inclusion of TA in γ-CD reduces the membrane permeability of the drug. A comparative analysis of the encapsulation of different NSAIDs in γCD-MOF was performed. The impact of NSAID structure on the loading capacity was considered for the first time. It was revealed that the presence of heterocycles in the structure and drug lipophilicity influence the loading efficiency of NSAIDs in γCD-MOF.

Citing Articles

Formulation Studies with Cyclodextrins for Novel Selenium NSAID Derivatives.

Ramos-Inza S, Moran-Serradilla C, Gaviria-Soteras L, Sharma A, Plano D, Sanmartin C Int J Mol Sci. 2024; 25(3).

PMID: 38338811 PMC: 10855879. DOI: 10.3390/ijms25031532.

References

Bennion B, Be N, McNerney M, Lao V, Carlson E, Valdez C . Predicting a Drug's Membrane Permeability: A Computational Model Validated With in Vitro Permeability Assay Data. J Phys Chem B. 2017; 121(20):5228-5237. DOI: 10.1021/acs.jpcb.7b02914. View

Hartlieb K, Ferris D, Holcroft J, Kandela I, Stern C, Nassar M . Encapsulation of Ibuprofen in CD-MOF and Related Bioavailability Studies. Mol Pharm. 2017; 14(5):1831-1839. DOI: 10.1021/acs.molpharmaceut.7b00168. View

Vavia P, Adhage N . Freeze-dried inclusion complexes of tolfenamic acid with beta-cyclodextrins. Pharm Dev Technol. 2000; 5(4):571-4. DOI: 10.1081/pdt-100102040. View

Al-Lawati H, Binkhathlan Z, Lavasanifar A . Nanomedicine for the effective and safe delivery of non-steroidal anti-inflammatory drugs: A review of preclinical research. Eur J Pharm Biopharm. 2019; 142:179-194. DOI: 10.1016/j.ejpb.2019.06.025. View

Kritskiy I, Volkova T, Surov A, Terekhova I . γ-Cyclodextrin-metal organic frameworks as efficient microcontainers for encapsulation of leflunomide and acceleration of its transformation into teriflunomide. Carbohydr Polym. 2019; 216:224-230. DOI: 10.1016/j.carbpol.2019.04.037. View

Nanri A, Yoshida M, Ishida Y, Nakata D, Terao K, Arce F . Preparation and Characterization of a Hybrid Complex of Cyclodextrin-Based Metal-Organic Frameworks-1 and Ascorbic Acid Derivatives. Materials (Basel). 2021; 14(23). PMC: 8658738. DOI: 10.3390/ma14237309. View

Pedersen S . Biopharmaceutical aspects of tolfenamic acid. Pharmacol Toxicol. 1994; 75 Suppl 2:22-32. DOI: 10.1111/j.1600-0773.1994.tb01992.x. View

Chen Y, Su J, Dong W, Xu D, Cheng L, Mao L . Cyclodextrin-based metal-organic framework nanoparticles as superior carriers for curcumin: Study of encapsulation mechanism, solubility, release kinetics, and antioxidative stability. Food Chem. 2022; 383:132605. DOI: 10.1016/j.foodchem.2022.132605. View

Zhou Y, Luo S, Niu B, Wu B, Fu J, Zhao Y . Ultramild One-Step Encapsulating Method as a Modular Strategy for Protecting Humidity-Susceptible Metal-Organic Frameworks Achieving Tunable Drug Release Profiles. ACS Biomater Sci Eng. 2021; 5(10):5180-5188. DOI: 10.1021/acsbiomaterials.9b01233. View

10.

Stasilowicz A, Tykarska E, Rosiak N, Salat K, Furgala-Wojas A, Plech T . The Inclusion of Tolfenamic Acid into Cyclodextrins Stimulated by Microenvironmental pH Modification as a Way to Increase the Anti-Migraine Effect. J Pain Res. 2021; 14:981-992. PMC: 8055370. DOI: 10.2147/JPR.S295795. View

11.

Kritskiy I, Volkova T, Sapozhnikova T, Mazur A, Tolstoy P, Terekhova I . Methotrexate-loaded metal-organic frameworks on the basis of γ-cyclodextrin: Design, characterization, in vitro and in vivo investigation. Mater Sci Eng C Mater Biol Appl. 2020; 111:110774. DOI: 10.1016/j.msec.2020.110774. View

12.

Fu J, Zhu J, Wang Z, Wang Y, Wang S, Yan R . Highly-efficient and selective adsorption of anionic dyes onto hollow polymer microcapsules having a high surface-density of amino groups: Isotherms, kinetics, thermodynamics and mechanism. J Colloid Interface Sci. 2019; 542:123-135. DOI: 10.1016/j.jcis.2019.01.131. View

13.

Khan K, Usman Minhas M, Badshah S, Suhail M, Ahmad A, Ijaz S . Overview of nanoparticulate strategies for solubility enhancement of poorly soluble drugs. Life Sci. 2022; 291:120301. DOI: 10.1016/j.lfs.2022.120301. View

14.

Li H, Lv N, Li X, Liu B, Feng J, Ren X . Composite CD-MOF nanocrystals-containing microspheres for sustained drug delivery. Nanoscale. 2017; 9(22):7454-7463. DOI: 10.1039/c6nr07593b. View

15.

Cagel M, Tesan F, Bernabeu E, Salgueiro M, Zubillaga M, Moretton M . Polymeric mixed micelles as nanomedicines: Achievements and perspectives. Eur J Pharm Biopharm. 2017; 113:211-228. DOI: 10.1016/j.ejpb.2016.12.019. View

16.

Liu B, Li H, Xu X, Li X, Lv N, Singh V . Optimized synthesis and crystalline stability of γ-cyclodextrin metal-organic frameworks for drug adsorption. Int J Pharm. 2016; 514(1):212-219. DOI: 10.1016/j.ijpharm.2016.09.029. View

17.

Smaldone R, Forgan R, Furukawa H, Gassensmith J, Slawin A, Yaghi O . Metal-organic frameworks from edible natural products. Angew Chem Int Ed Engl. 2010; 49(46):8630-4. DOI: 10.1002/anie.201002343. View

18.

Muankaew C, Loftsson T . Cyclodextrin-Based Formulations: A Non-Invasive Platform for Targeted Drug Delivery. Basic Clin Pharmacol Toxicol. 2017; 122(1):46-55. DOI: 10.1111/bcpt.12917. View

19.

Forgan R, Smaldone R, Gassensmith J, Furukawa H, Cordes D, Li Q . Nanoporous carbohydrate metal-organic frameworks. J Am Chem Soc. 2011; 134(1):406-17. DOI: 10.1021/ja208224f. View

20.

Costa P, Sousa Lobo J . Modeling and comparison of dissolution profiles. Eur J Pharm Sci. 2001; 13(2):123-33. DOI: 10.1016/s0928-0987(01)00095-1. View