2017 |
Sierpe, R; Noyong, M; Simon, U; Aguayo, D; Huerta, J; Kogan, M J; Yutronic, N Construction of 6-Thioguanine and 6-Mercaptopurine Carriers Based on Beta Cyclodextrins and Gold Nanoparticles Artículo de revista Carbohydrate Polymers, 177 , pp. 22-31, 2017, ISSN: 0144-8617. Resumen | Enlaces | BibTeX | Etiquetas: anisotropic antineoplastic, applications, cancer, complex, complexes, cytotoxicity delivery, dielectrics, drug drug-delivery, enhanced inclusion ionic-solutions, nanotechnology, permeability, pharmaceutical photothermal solid-state, sputtering, therapy @article{RN352, title = {Construction of 6-Thioguanine and 6-Mercaptopurine Carriers Based on Beta Cyclodextrins and Gold Nanoparticles}, author = { R. Sierpe and M. Noyong and U. Simon and D. Aguayo and J. Huerta and M.J. Kogan and N. Yutronic}, url = {/brokenurl#<Go to ISI>://WOS:000411876200003}, doi = {10.1016/j.carbpol.2017.08.102}, issn = {0144-8617}, year = {2017}, date = {2017-01-01}, journal = {Carbohydrate Polymers}, volume = {177}, pages = {22-31}, abstract = {As a novel strategy to overcome some of the therapeutic disadvantages of 6-thioguanine (TG) and 6-mercaptopurine (MP), we propose the inclusion of these drugs in beta cyclodextrin (beta CD) to form the complexes beta CD-TG and beta CD-MP, followed by subsequent interaction with gold nanoparticles (AuNPs), generating the ternary systems: beta CD-TG-AuNPs and beta CD-MP-AuNPs. This modification increased their solubility and improved their stability, betting by a site-specific transport due to their nanometric dimensions, among other advantages., The formation of the complexes was confirmed using powder X-ray diffraction, thermogravimetric analysis and one and two-dimensional NMR. A theoretical study using DFT and molecular modelling was conducted to obtain the more stable tautomeric species of TG and MP in solution and confirm the proposed inclusion geometries. The deposition of AuNPs onto beta CD-TG and beta CD-MP via sputtering was confirmed by UV-vis spectroscopy. Subsequently, the ternary systems were characterized by TEM, FE-SEM and EDX to directly observe the deposited AuNPs and evaluate their sizes, size dispersion, and composition. Finally, the in vitro permeability of the ternary systems was studied using parallel artificial membrane permeability assay (PAMPA).}, keywords = {anisotropic antineoplastic, applications, cancer, complex, complexes, cytotoxicity delivery, dielectrics, drug drug-delivery, enhanced inclusion ionic-solutions, nanotechnology, permeability, pharmaceutical photothermal solid-state, sputtering, therapy}, pubstate = {published}, tppubtype = {article} } As a novel strategy to overcome some of the therapeutic disadvantages of 6-thioguanine (TG) and 6-mercaptopurine (MP), we propose the inclusion of these drugs in beta cyclodextrin (beta CD) to form the complexes beta CD-TG and beta CD-MP, followed by subsequent interaction with gold nanoparticles (AuNPs), generating the ternary systems: beta CD-TG-AuNPs and beta CD-MP-AuNPs. This modification increased their solubility and improved their stability, betting by a site-specific transport due to their nanometric dimensions, among other advantages., The formation of the complexes was confirmed using powder X-ray diffraction, thermogravimetric analysis and one and two-dimensional NMR. A theoretical study using DFT and molecular modelling was conducted to obtain the more stable tautomeric species of TG and MP in solution and confirm the proposed inclusion geometries. The deposition of AuNPs onto beta CD-TG and beta CD-MP via sputtering was confirmed by UV-vis spectroscopy. Subsequently, the ternary systems were characterized by TEM, FE-SEM and EDX to directly observe the deposited AuNPs and evaluate their sizes, size dispersion, and composition. Finally, the in vitro permeability of the ternary systems was studied using parallel artificial membrane permeability assay (PAMPA). |
2016 |
Silva, N; Moris, S; Diaz, M; Yutronic, N; Lang, E; Chornik, B; Kogan, M J; Jara, P Evidence of the Disassembly of Alpha-Cyclodextrin-Octylamine Inclusion Compounds Conjugated to Gold Nanoparticles Via Thermal and Photothermal Effects Artículo de revista Molecules, 21 (11), 2016. Resumen | Enlaces | BibTeX | Etiquetas: beta-cyclodextrin, complex, compounds, constants, core crystals, cyclodextrin, effects, gold inclusion nanoparticles, octylamine, photothermal @article{RN301, title = {Evidence of the Disassembly of Alpha-Cyclodextrin-Octylamine Inclusion Compounds Conjugated to Gold Nanoparticles Via Thermal and Photothermal Effects}, author = { N. Silva and S. Moris and M. Diaz and N. Yutronic and E. Lang and B. Chornik and M.J. Kogan and P. Jara}, url = {/brokenurl#<Go to ISI>://WOS:000389918200026}, doi = {10.3390/molecules21111444}, year = {2016}, date = {2016-01-01}, journal = {Molecules}, volume = {21}, number = {11}, abstract = {Cyclodextrin (CD) molecules form inclusion compounds (ICs), generating dimers that are capable of encapsulating molecules derived from long-chain hydrocarbons. The aim of this study is to evaluate the structural changes experienced by ICs in solution with increasing temperatures. For this, a nuclear magnetic resonance (H-1-NMR) titration was performed to determinate the stoichiometric alpha-cyclodextrin (alpha-CD):octylamine (OA) 2:1 and binding constant (k = 2.16 M-2) of ICs. Solution samples of alpha-CD-OA ICs conjugated with gold nanoparticles (AuNPs) were prepared, and H-1-NMR spectra at different temperatures were recorded. Comparatively, H-1-NMR spectra of the sample irradiated with a laser with tunable wavelengths, with plasmons of conjugated AuNPs, were recorded. In this work, we present evidence of the disassembly of ICs conjugated with AuNPs. Thermal studies demonstrated that, at 114 degrees C, there are reversible rearrangements of the host and guests in the ICs in a solid state. Migration movements of the guest molecules from the CD cavity were monitored via temperature-dependent H-1-NMR, and were verified comparing the chemical shifts of octylamine dissolved in deuterated dimethylsulfoxide (DMSO-d(6)) with the OA molecule included in alpha-CD dissolved in the same solvent. It was observed that, at 117 degrees C, OA exited the alpha-CD cavity. CD IC dimer disassembly was also observed when the sample was irradiated with green laser light.}, keywords = {beta-cyclodextrin, complex, compounds, constants, core crystals, cyclodextrin, effects, gold inclusion nanoparticles, octylamine, photothermal}, pubstate = {published}, tppubtype = {article} } Cyclodextrin (CD) molecules form inclusion compounds (ICs), generating dimers that are capable of encapsulating molecules derived from long-chain hydrocarbons. The aim of this study is to evaluate the structural changes experienced by ICs in solution with increasing temperatures. For this, a nuclear magnetic resonance (H-1-NMR) titration was performed to determinate the stoichiometric alpha-cyclodextrin (alpha-CD):octylamine (OA) 2:1 and binding constant (k = 2.16 M-2) of ICs. Solution samples of alpha-CD-OA ICs conjugated with gold nanoparticles (AuNPs) were prepared, and H-1-NMR spectra at different temperatures were recorded. Comparatively, H-1-NMR spectra of the sample irradiated with a laser with tunable wavelengths, with plasmons of conjugated AuNPs, were recorded. In this work, we present evidence of the disassembly of ICs conjugated with AuNPs. Thermal studies demonstrated that, at 114 degrees C, there are reversible rearrangements of the host and guests in the ICs in a solid state. Migration movements of the guest molecules from the CD cavity were monitored via temperature-dependent H-1-NMR, and were verified comparing the chemical shifts of octylamine dissolved in deuterated dimethylsulfoxide (DMSO-d(6)) with the OA molecule included in alpha-CD dissolved in the same solvent. It was observed that, at 117 degrees C, OA exited the alpha-CD cavity. CD IC dimer disassembly was also observed when the sample was irradiated with green laser light. |
2017 |
Construction of 6-Thioguanine and 6-Mercaptopurine Carriers Based on Beta Cyclodextrins and Gold Nanoparticles Artículo de revista Carbohydrate Polymers, 177 , pp. 22-31, 2017, ISSN: 0144-8617. |
2016 |
Evidence of the Disassembly of Alpha-Cyclodextrin-Octylamine Inclusion Compounds Conjugated to Gold Nanoparticles Via Thermal and Photothermal Effects Artículo de revista Molecules, 21 (11), 2016. |