Computational simulation of nanostructured lipid carrier containing lipids from Cupuassu (Theobroma grandiflorum) seed fat: Design, interaction and molecular dynamic study
DOI:
https://doi.org/10.33448/rsd-v9i11.10433Keywords:
Computational simulation; Nanostructured lipid carrier; Cupuassu.Abstract
Drug delivery systems are constantly evolving and developing, as well as the search for promising and effective formulations for drug delivery. Computational simulation methods enable the development of complex systems, such as nanostructured lipid carriers (NLC), the understanding of interaction and dynamics between drug molecule and its transporter. In this work, aimed to simulate a NLC containing cupuassu fat triacylglycerols, carnauba wax and caprylic/capric acid triacylglycerol, stabilized with Tween 80 and Pluronic and ketoconazole enantiomer as drug was simulated. Initially, lipid mixtures were studied by Differential Scanning Calorimetry and X-ray diffraction. Subsequently, computational studies were carried out, among which Molecular Docking of ketoconazole to the lipid mixture and Molecular Dynamics of NLC system containing ketoconazole. From the results obtained it was possible to observe the main binding affinities of the drug and provide a better NLC formulation. It was also possible to propose a three-dimensional NLC model that was stable after molecular dynamics and ideal for future experimental studies.
References
Arroio, A., Honório, K. M., & Silva, A. B. F. da. (2010). Quantum chemical properties used in structure-activity relationship studies. Química Nova, 33(3), 694–699. Doi:10.1590/S0100-40422010000300037
Brancolini, G., Kokh, D. B., Calzolai, L., Wade, R. C., & Corni, S. (2012). Docking of Ubiquitin to Gold Nanoparticles. ACS Nano, 6(11), 9863–9878. Doi:10.1021/nn303444b
Bruxel, F., Laux, M., Wild, L. B., Fraga, M., Koester, L. S., & Teixeira, H. F. (2012). Nanoemulsões como sistemas de liberação parenteral de fármacos. Química Nova, 35(9), 1827–1840. Doi:10.1590/S0100-40422012000900023
Carvalho, I., Pupo, M. T., Borges, Á. D. L., & Bernardes, L. S. C. (2003). Introdução a modelagem molecular de fármacos no curso experimental de química farmacêutica. Química Nova, 26(3), 428–438. Doi:10.1590/S0100-40422003000300023
Costa, R. S. da, Santos, O. V. dos, Lannes, S. C. da S., Casazza, A. A., Aliakbarian, B., Perego, P., Ribeiro-Costa, R. M., Converti, A., & Silva Júnior, J. O. C. (2020). Bioactive compounds and value-added applications of cupuassu (Theobroma grandiflorum Schum.) agroindustrial by-product. Food Science and Technology, 40(2), 401–407. Doi:10.1590/fst.01119
Desai, P. V., Raub, T. J., & Blanco, M.-J. (2012). How hydrogen bonds impact P-glycoprotein transport and permeability. Bioorganic & Medicinal Chemistry Letters, 22(21), 6540–6548. Doi: 10.1016/j.bmcl.2012.08.059
Engel, T., & Reid, P. (2006). Quantum Chemistry and Spectroscopy with Spartan Student Physical Chemistry Software. Washington: Prentice Hall.
Galindo, M.V., Paglione, I. dos S., Coelho, A. R., Leimann, F. V., & Shirai, M. A. (2020). Production of chitosan nanoparticles and application as coating in starch and poly(lactic acid) sheets. Research, Society and Development, 9(9), 1-15. Doi:10.33448/rsd-v9i9.7694
Gilabert‐Escrivá, M. V., Gonçalves, L. A. G., Silva, C. R. S., & Figueira, A. (2002). Fatty acid and triacylglycerol composition and thermal behaviour of fats from seeds of Brazilian Amazonian Theobroma species. Journal of the Science of Food and Agriculture, 82(13), 1425–1431. Doi: 10.1002/jsfa.1107
Haider, M., Abdin, S. M., Kamal, L., & Orive, G. (2020). Nanostructured Lipid Carriers for Delivery of Chemotherapeutics: A Review. Pharmaceutics, 12(3). Doi:10.3390/pharmaceutics12030288
Jämbeck, J. P. M., Eriksson, E. S. E., Laaksonen, A., Lyubartsev, A. P., & Eriksson, L. A. (2014). Molecular Dynamics Studies of Liposomes as Carriers for Photosensitizing Drugs: Development, Validation, and Simulations with a Coarse-Grained Model. Journal of Chemical Theory and Computation, 10(1), 5–13. Doi:10.1021/ct400466m
Klein, C., & Dutrow, B. (2009). Manual de Ciência dos Minerais. Porto Alegre: Bookman Editora.
Lacatusu, I., Niculae, G., Badea, N., Stan, R., Popa, O., Oprea, O., & Meghea, A. (2014). Design of soft lipid nanocarriers based on bioactive vegetable oils with multiple health benefits. Chemical Engineering Journal, 246, 311–321. Doi:10.1016/j.cej.2014.02.041
Lai, L., & Barnard, A. S. (2015). Functionalized Nanodiamonds for Biological and Medical Applications. Journal of Nanoscience and Nanotechnology, 15(2), 989–999. Doi:10.1166/jnn.2015.9735
Lee, H., & Pastor, R. W. (2011). Coarse-Grained Model for PEGylated Lipids: Effect of PEGylation on the Size and Shape of Self-Assembled Structures. The Journal of Physical Chemistry B, 115(24), 7830–7837. Doi:10.1021/jp2020148
Martínez, L., Andrade, R., Birgin, E. G., & Martínez, J. M. (2009). PACKMOL: A package for building initial configurations for molecular dynamics simulations. Journal of Computational Chemistry, 30(13), 2157–2164. https://Doi.org/10.1002/jcc.21224
Martins, C. R., Lopes, W. A., & Andrade, J. B. de. (2013). Organic compound solubility. Química Nova, 36(8), 1248–1255. Doi:10.1590/S0100-40422013000800026
Milanovic, J., Manojlovic, V., Levic, S., Rajic, N., Nedovic, V., & Bugarski, B. (2010). Microencapsulation of flavors in carnauba wax. Sensors (Basel, Switzerland), 10(1), 901–912. Doi:10.3390/s100100901
Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F. Belew, R.K., Goodsell, D.S., & Olson, A.J. (2009). AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility, J. Comput. Chem. 30, 2785–2791. Doi:10.1002/jcc.21256
Namba, A. M., Silva, V. B. da, & Silva, C. H. T. P. da. (2008). Dinâmica molecular: Teoria e aplicações em planejamento de fármacos. Eclética Química, 33(4), 13–23. Retrieved from https://www.scielo.br/pdf/eq/v33n4/v33n4a02.pdf
Novotná, A., Krasulová, K., Bartoňková, I., Korhoňová, M., Bachleda, P., Anzenbacher, P., & Dvořák, Z. (2014). Dual Effects of Ketoconazole cis-Enantiomers on CYP3A4 in Human Hepatocytes and HepG2 Cells. PLoS ONE, 9(10). Doi:10.1371/journal.pone.0111286
Pereira, A. S., Shitsuka, D. M., Parreira, F. J, & Shitsuka, R. (2018). Metodologia da pesquisa Científica. Rio Grande do Sul: Universidade Federal de Santa Maria.
Plumley, J. A., & Dannenberg, J. J. (2011). A comparison of the behavior of functional/basis set combinations for hydrogen-bonding in the water dimer with emphasis on basis set superposition error. Journal of Computational Chemistry, 32(8), 1519–1527. Doi:10.1002/jcc.21729
Puri, A., Loomis, K., Smith, B., Lee, J.-H., Yavlovich, A., Heldman, E., & Blumenthal, R. (2009). Lipid-Based Nanoparticles as Pharmaceutical Drug Carriers: From Concepts to Clinic. Critical reviews in therapeutic drug carrier systems, 26(6), 523–580. Retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2885142/
Quast, L. B., Luccas, V., & Kieckbusch, T. G. (2011). Physical properties of pre-crystallized mixtures of cocoa butter and cupuassu fat. Grasas y Aceites, 62(1), 62–67. Doi:10.3989/gya.034010
Ramezani, M., & Shamsara, J. (2016). Application of DPD in the design of polymeric nano-micelles as drug carriers. Journal of Molecular Graphics and Modelling, 66, 1–8. Doi:10.1016/j.jmgm.2016.01.010
Ramezanpour, M., Leung, S. S. W., Delgado-Magnero, K. H., Bashe, B. Y. M., Thewalt, J., & Tieleman, D. P. (2016). Computational and experimental approaches for investigating nanoparticle-based drug delivery systems. Biochimica et Biophysica Acta (BBA) - Biomembranes, 1858, 1688–1709. Doi:10.1016/j.bbamem.2016.02.028
Razmimanesh, F., Amjad-Iranagh, S., & Modarress, H. (2015). Molecular dynamics simulation study of chitosan and gemcitabine as a drug delivery system. Journal of Molecular Modeling, 21(7), 165. Doi:10.1007/s00894-015-2705-2
Rosa, R. L. da, Serbai, L., Novak, R. S., Paula, J. de F. P. de, Toledo, A. C. O., Carvalho, V. V. M. de, & Boscardin, P. M. D. (2020). Development and evaluation of organic silicon nanoparticles. Brazilian Journal of Development, 6(3), 13180–13190. Doi:10.34117/bjdv6n3-255
Salvi, V. R., & Pawar, P. (2019). Nanostructured lipid carriers (NLC) system: A novel drug targeting carrier. Journal of Drug Delivery Science and Technology, 51, 255–267. Doi:10.1016/j.jddst.2019.02.017
Sant’Anna, C. M. R. (2009). Métodos de Modelagem Molecular para Estudo e Planejamento de Compostos Bioativos: Uma Introduçao. Revista Virtual de Química, 1(1), 49–57. Doi:10.5935/1984-6835.20090007
Santos, G. S. dos, Pereira, G. G., Bender, E. A., Colomé, L. M., Guterres, S. S., Carvalho, D. C. M. de, & Weissmüller, G. (2012). Desenvolvimento e caracterização de nanopartículas lipídicas destinadas à aplicação tópica de dapsona. Química Nova, 35(7), 1388–1394. Doi:10.1590/S0100-40422012000700019
Silva, J. C., Plivelic, T. S., Herrera, M. L., Ruscheinsky, N., Kieckbusch, T. G., Luccas, V., & Torriani, I. L. (2009). Polymorphic Phases of Natural Fat from Cupuassu (Theobroma grandiflorum) Beans: A WAXS/SAXS/DSC Study. Crystal Growth & Design, 9(12), 5155–5163. Doi:10.1021/cg901081j
Silva, J. D. de S., Leite, S. da C., Silva, M. T. S. da, Meirelles, L. M. A., & Andrade, A. W. L. (2020). In silico evaluation of the inhibitory effect of antiretrovirals Atazanavir and Darunavir on the main protease of SARS-CoV-2: docking studies and molecular dynamics. Research, Society and Development, 9(8). Doi:10.33448/rsd-v9i8.6562
Silva, N. de F., da Silva, R. L., Almeida, K. de O., Nascimento-Júnior, A. E. S. do, Brasil, D. do S. B., Silva-Júnior, J. O. C., Teixeira, F. M., & Ribeiro-Costa, R. M. (2017). Study of molecular interactions between Chitosan and Vi Antigen. Journal of Molecular Graphics and Modelling, 72, 148–155. Doi:10.1016/j.jmgm.2016.12.015
Souto, E. B., Mehnert, W., & Müller, R. H. (2006). Polymorphic behaviour of Compritol®888 ATO as bulk lipid and as SLN and NLC. Journal of Microencapsulation, 23(4), 417–433. Doi:10.1080/02652040600612439
Souto, F. L. G. (2013). Obtenção e caracterização de carreadores lipídicos nanoestruturados a partir de gordura vegetal de Cupuassu (Theobroma grandiflorum). Belém: Universidade Federal do Pará.
Todorova, N., Chiappini, C., Mager, M., Simona, B., Patel, I. I., Stevens, M. M., & Yarovsky, I. (2014). Surface Presentation of Functional Peptides in Solution Determines Cell Internalization Efficiency of TAT Conjugated Nanoparticles. Nano Letters, 14(9), 5229–5237. Doi:10.1021/nl5021848
Van Der Spoel, D., Lindahl, E., Hess, B., Groenhof, G., Mark, A. E., & Berendsen, H. J. C. (2005). GROMACS: Fast, flexible, and free. Journal of Computational Chemistry, 26(16), 1701–1718. Doi:10.1002/jcc.20291
Villalobos-Hernández, J. R., & Müller-Goymann, C. C. (2006). Sun protection enhancement of titanium dioxide crystals by the use of carnauba wax nanoparticles: The synergistic interaction between organic and inorganic sunscreens at nanoscale. International Journal of Pharmaceutics, 322(1–2), 161–170. Doi:10.1016/j.ijpharm.2006.05.037
Wang, X.-Y., Zhang, L., Wei, X.-H., & Wang, Q. (2013). Molecular dynamics of paclitaxel encapsulated by salicylic acid-grafted chitosan oligosaccharide aggregates. Biomaterials, 34(7), 1843–1851. Doi:10.1016/j.biomaterials.2012.11.024
Yang, Y., Corona, A., Schubert, B., Reeder, R., & Henson, M. A. (2014). The effect of oil type on the aggregation stability of nanostructured lipid carriers. Journal of Colloid and Interface Science, 418, 261–272. Doi:10.1016/j.jcis.2013.12.024
Xu, D., Martin, C., & Schulten, K. (1996). Molecular Dynamic Study of Early Picosecond events in the bacteriorhodopdin photocicly: Dieletric response vibrational cooling and the J, K intermediates. Biophys. J, 70, 453-460. Doi:10.1016/S0006-3495(96)79588-7
Zhang, G., & Musgrave, C. B. (2007). Comparison of DFT Methods for Molecular Orbital Eigenvalue Calculations. The Journal of Physical Chemistry A, 111(8), 1554–1561. Doi:10.1021/jp061633o
Zhang, S., Sun, H.-J., Hughes, A. D., Moussodia, R.-O., Bertin, A., Chen, Y., Pochan, D. J., Heiney, P. A., Klein, M. L., & Percec, V. (2014). Self-assembly of amphiphilic Janus dendrimers into uniform onion-like dendrimersomes with predictable size and number of bilayers. Proceedings of the National Academy of Sciences of the United States of America, 111(25), 9058–9063. Doi:10.1073/pnas.1402858111
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