Hostname: page-component-586b7cd67f-2brh9 Total loading time: 0 Render date: 2024-11-30T19:47:56.784Z Has data issue: false hasContentIssue false
  • English
  • Français

Adsorption of 5-aminosalicylic acid on kaolinite surfaces at a molecular level

Published online by Cambridge University Press:  01 April 2019

Mahmoud E. Awad Open the ORCID record for Mahmoud E. Awad [Opens in a new window] ,
Elizabeth Escamilla-Roa ,
Ana Borrego-Sánchez ,
César Viseras ,
Alfonso Hernández-Laguna  and
C. Ignacio Sainz-Díaz
Mahmoud E. Awad*
Affiliation:
Department of Geology, Faculty of Science, Al Azhar University in Cairo, Nasr City, 11884, Egypt Department of Pharmacy and Pharmaceutical Technology, School of Pharmacy, University of Granada, 18071, Granada, Spain Instituto Andaluz de Ciencias de la Tierra, CSIC-UGR, Av. de las Palmeras 4, 18100 Armilla, Granada, Spain
Elizabeth Escamilla-Roa
Affiliation:
Instituto Andaluz de Ciencias de la Tierra, CSIC-UGR, Av. de las Palmeras 4, 18100 Armilla, Granada, Spain Department of Computer Science, Electrical and Space Engineering, Luleå University of Technology, 97187 Luleå, Sweden
Ana Borrego-Sánchez
Affiliation:
Department of Pharmacy and Pharmaceutical Technology, School of Pharmacy, University of Granada, 18071, Granada, Spain Instituto Andaluz de Ciencias de la Tierra, CSIC-UGR, Av. de las Palmeras 4, 18100 Armilla, Granada, Spain
César Viseras
Affiliation:
Department of Pharmacy and Pharmaceutical Technology, School of Pharmacy, University of Granada, 18071, Granada, Spain Instituto Andaluz de Ciencias de la Tierra, CSIC-UGR, Av. de las Palmeras 4, 18100 Armilla, Granada, Spain
Alfonso Hernández-Laguna
Affiliation:
Instituto Andaluz de Ciencias de la Tierra, CSIC-UGR, Av. de las Palmeras 4, 18100 Armilla, Granada, Spain
C. Ignacio Sainz-Díaz
Affiliation:
Instituto Andaluz de Ciencias de la Tierra, CSIC-UGR, Av. de las Palmeras 4, 18100 Armilla, Granada, Spain
*
*E-mail: [email protected]
Get access Rights & Permissions [Opens in a new window]

Abstract

The application of clay minerals in therapeutics is becoming important due to their structural and surface physicochemical properties. 5-aminosalicylic acid (5-ASA) is a very common pharmaceutical drug and is used worldwide. The interactions between the 5-ASA molecule and both the aluminol and siloxane surfaces of kaolinite are studied by means of atomistic calculations using force fields based on empirical interatomic potentials and quantum mechanics calculations based on density functional theory. A conformational analysis of 5-ASA has been performed and the anion of 5-ASA was also studied. The calculated adsorption energy values indicate that 5-ASA is likely to be adsorbed on the kaolinite surfaces with greater affinity to the aluminol surface. Hence, kaolinite may be considered as a promising pharmaceutical carrier of 5-ASA.

Keywords

kaolinite5-aminosalicylic acidmesalazineadsorptionsurfacemolecular modellingatomistic calculationspharmaceutical carrier
Type
Article
Information
Clay Minerals , Volume 54 , Issue 1 , March 2019 , pp. 49 - 56
Copyright
Copyright © Mineralogical Society of Great Britain and Ireland 2019 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

Footnotes

Guest Associate Editor: Hendrik Heinz

References

Aarset, K., Page, E.M. & Rice, D.A. (2006) Molecular structures of benzoic acid and 2-hydroxybenzoic acid, obtained by gas-phase electron diffraction and theoretical calculations. Journal of Physical Chemistry A, 110, 9014–9019.Google Scholar
Aguzzi, C., Viseras, C., Cerezo, P., Salcedo, I., Sánchez-Espejo, R. & Valenzuela, C. (2013) Release kinetics of 5-aminosalicylic acid from halloysite. Colloids and Surfaces B: Biointerfaces, 105, 75–80.Google Scholar
Allgayer, H., Sonnenbichler, J., Kruis, W. & Paumgartner, G. (1985) Determination of the pK values of 5-aminosalicylic acid and N-acetylaminosalicylic acid and comparison of the pH dependent lipid–water partition coefficients of sulphasalazine and its metabolites. Arzneimittelforschung, 35, 1457–1459.Google Scholar
Awad, M.E., López-Galindo, A., Setti, M., El-Rahmany, M.M. & Iborra, C.V. (2017) Kaolinite in pharmaceutics and biomedicine. International Journal of Pharmaceutics, 533, 34–48.Google Scholar
Bello, M.L., Junior, A.M., Vieira, B.A., Dias, L.R.S., de Sousa, V.P., Castro, H.C., Rodrigues, C.R. & Cabral, L.M. (2015) Sodium montmorillonite/amine-containing drugs complexes: new insights on intercalated drugs arrangement into layered carrier material. PLoS One, 10, e0121110.Google Scholar
Belzunces, B., Hoyau, S., Benoit, M., Tarrat, N. & Bessac, F. (2017) Theoretical study of the atrazine pesticide interaction with pyrophyllite and Ca2+-montmorillonite clay surfaces. Journal of Computational Chemistry, 38, 133–143.Google Scholar
BIOVIA (2016) Materials Studio, Version 2016. Dassault Systems, Vélizy-Villacoublay, France.Google Scholar
Bish, D.L. (1993) Rietveld refinement of the kaolinite structure at 1.5 K. Clays and Clay Minerals, 41, 738–744.Google Scholar
Bohm, S.K. & Kruis, W. (2014) Long-term efficacy and safety of once-daily mesalazine granules for the treatment of active ulcerative colitis. Clinical Experimental Gastroenterology, 7, 369–383.Google Scholar
Borrego-Sánchez, A., Awad, M.E. & Sainz-Díaz, C.I. (2018a) Molecular modeling of adsorption of 5-aminosalicylic acid in the halloysite nanotube. Minerals, 8, 61.Google Scholar
Borrego-Sánchez, A., Carazo, E., Aguzzi, C., Viseras, C. & Sainz-Díaz, C.I. (2018b) Biopharmaceutical improvement of praziquantel by interaction with montmorillonite and sepiolite. Applied Clay Science, 160, 173–179.Google Scholar
Brigatti, M.F., Sainz-Díaz, C.I., Borsari, M., Bernini, F., Castellini, E. & Malferrari, D. (2017) Crystal chemical characterization and computational modeling of a μ-oxoFe (III) complex with 1,10-phenanthroline clarify its interaction and reactivity with montmorillonite. Rendiconti Lincei, 28, 1–10.Google Scholar
Escamilla-Roa, E., Huertas, F.J., Hernádez-laguna, A. & Sainz-Díaz, C.I. (2017) A DFT study of the adsorption of glycine in the interlayer space of montmorillonite. Physical Chemistry and Chemical Physics, 19, 14961–14971.Google Scholar
Escamilla-Roa, E. & Sainz-Díaz, C.I. (2014) Amorphous ammonia–water ice deposited onto silicate grain: effect on growth of mantles ice on interstellar and interplanetary dust. Journal of Physical Chemistry C, 118, 3554–3563.Google Scholar
Francisco-Márquez, M., Soriano-Correa, C. & Sainz-Díaz, C.I. (2017) Adsorption of sulfonamides on phyllosilicate surfaces by molecular modeling calculations. The Journal of Physical Chemistry C, 121, 2905–2914.Google Scholar
Grimme, S. (2006) Semiempirical GGA-type density functional constructed with a long-range dispersion correction. Journal of Computational Chemistry, 27, 1787–1799.Google Scholar
Hauso, Ø., Martinsen, T.C. & Waldum, H. (2015) 5-aminosalicylic acid, a specific drug for ulcerative colitis. Scandinavian Journal of Gastroenterology, 50, 933–941.Google Scholar
Heinz, H., Lin, T.J., Mishra, R.K. & Emami, F.S. (2013) Thermodynamically consistent force fields for the assembly of inorganic, organic, and biological nanostructures: the interface force field. Langmuir, 29, 1754–1765.Google Scholar
Heinz, H., Vaia, R.A. & Farmer, B.L. (2006) Interaction energy and surface reconstruction between sheets of layered silicates. Journal of Chemical Physics, 124, 224713.Google Scholar
Kubicki, J.D. (2016) Molecular Modeling of Geochemical Reactions. An Introduction. Wiley, Chichester, UK.Google Scholar
Laursen, L.S., Stokholm, M., Bukhave, K., Rask-Madsen, J. & Lauritsen, K. (1990) Disposition of 5-aminosalicylic acid by olsalazine and three mesalazine preparations in patients with ulcerative colitis: comparison of intraluminal colonic concentrations, serum values, and urinary excretion. Gut, 31, 1271–1276.Google Scholar
Li, X., Li, H. & Yang, G. (2015) Promoting the adsorption of metal ions on kaolinite by defect sites: a molecular dynamics study. Scientific Reports, 5, 14377.Google Scholar
Liu, Y., Zhao, J., Li, F. & Chen, Z. (2013) Appropriate description of intermolecular interactions in the methane hydrates: an assessment of DFT methods. Journal of Computational Chemistry, 34, 121–131.Google Scholar
Martos-Villa, R., Francisco-Márquez, M., Mata, M.P. & Sainz-Díaz, C.I. (2013) Crystal structure, stability and spectroscopic properties of methane and CO2 hydrates. Journal of Molecular Graphics and Modeling, 44, 253–265.Google Scholar
Martos-Villa, R., Mata, M.P. & Sainz-Díaz, C.I. (2014) Characterization of CO2 and mixed methane/CO2 hydrates intercalated in smectites by means of atomistic calculations. Journal of Molecular Graphics and Modeling, 49, 80–90.Google Scholar
Orsi, M. (2014) Molecular dynamics simulation of humic substances. Chemical and Biological Technologies in Agriculture, 1, 1–14.Google Scholar
Ouyang, D. & Smith, S.C. (2015) Computational Pharmaceutics: Application of Molecular Modeling in Drug Delivery. John Wiley & Sons, Chichester, UK.Google Scholar
Patwardhan, S.V., Emami, F.S., Berry, R.J., Jones, S.E., Naik, R.R., Deschaume, O., Heinz, H. & Perry, C.C. (2012) Chemistry of aqueous silica nanoparticle surfaces and the mechanism of selective peptide adsorption. Journal of the American Chemical Society, 134, 6244–6256.Google Scholar
Pruitt, R., Hanson, J., Safdi, M., Wruble, L., Hardi, R., Johanson, J., Koval, G., Riff, D., Winston, B., Cross, A., Doty, P. & Johnson, L.K. (2002) Balsalazide is superior to mesalamine in the time to improvement of signs and symptoms of acute mild-to-moderate ulcerative colitis. The American Journal of Gastroenterology, 97, 3078–3086.Google Scholar
Qiu, X., Ma, J., Wang, K. & Zhang, H. (2016) Chemopreventive effects of 5-aminosalicylic acid on inflammatory bowel disease-associated colorectal cancer and dysplasia: a systematic review with meta-analysis. Oncotarget, 30, 1031–1045.Google Scholar
Rautureau, M., Gomes, C.F., Liewig, N. & Katouzian-Safadi, M. (2017) Clays and Health: Properties and Therapeutic Uses. Springer International Publishing AG, Basel, Switzerland.Google Scholar
Sainz-Díaz, C.I. (2011) Applications of computational atomistic methods to phyllosilicates. Pp. 203–238 in: Layered Mineral Structures and Their Application in Advanced Technologies (Brigatti, M.F. & Mottana, A., editors). EMU Notes in Mineralogy, 11. European Mineralogical Union & Mineralogical Society of Great Britain and Ireland, London, UK.Google Scholar
Sokollik, C., Fournier, N., Rizzuti, D., Braegger, C.P., Nydegger, A., Schibli, S. & Spalinger, J. (2017) The use of 5-aminosalicylic acid in children and adolescents with inflammatory bowel disease. Journal of Clinical Gastroenterology, 51, e87–e91.Google Scholar
Tan, D., Yuan, P., Bergaya, F.A., Liu, D. & He, H. (2014) High-capacity loading of 5-fluorouracil on the methoxy modified kaolinite. Applied Clay Science, 100, 60–65.Google Scholar
Tkatchenko, A. & Scheffler, M. (2009) Accurate molecular van der Waals interactions from ground-state electron density and free-atom reference data. Physical Reviews Letters, 10, 073005.Google Scholar
Viseras, M.T., Aguzzi, C., Cerezo, P., Viseras, C. & Valenzuela, C. (2008) Equilibrium and kinetics of 5-aminosalicylic acid adsorption by halloysite. Microporous and Mesoporous Materials, 108, 112–116.Google Scholar
Ye, B. & Langenberg, D.R. (2015) Mesalazine preparations for the treatment of ulcerative colitis: are all created equal? World Journal of Gastrointestinal Pharmacology and Therapeutics, 6, 137–144.Google Scholar
Yu, C.H., Newton, S.Q., Miller, D.M., Teppen, B.J. & Schäfer, L. (2001) Ab initio study of the nonequivalence of adsorption of d- and l-peptides on clay mineral surfaces. Structural Chemistry, 12, 393–398.Google Scholar
Yu, C.H., Norman, M.A., Newton, S.Q., Miller, D.M., Teppen, B.J. & Schäfer, L. (2000) Molecular dynamics simulations of the adsorption of proteins on clay mineral surfaces. Journal of Molecular Structure, 556, 95–103.Google Scholar