2017 |
Asela, I; Noyong, M; Simon, U; Andrades-Lagos, J; Campanini-Salinas, J; Vasquez-Velasquez, D; Kogan, M; Yutronic, N; Sierpe, R Gold Nanoparticles Stabilized with Beta Cyclodextrin-2-Amino-4-(4-Chlorophenyl)Thiazole Complex: A Novel System for Drug Transport Artículo de revista Plos One, 12 (10), 2017, ISSN: 1932-6203. Resumen | Enlaces | BibTeX | Etiquetas: activity, beta-cyclodextrin, complexes, delivery-systems, inclusion organophosphorus pesticides, photodegradation rates, thiazoles @article{RN353, title = {Gold Nanoparticles Stabilized with Beta Cyclodextrin-2-Amino-4-(4-Chlorophenyl)Thiazole Complex: A Novel System for Drug Transport}, author = { I. Asela and M. Noyong and U. Simon and J. Andrades-Lagos and J. Campanini-Salinas and D. Vasquez-Velasquez and M. Kogan and N. Yutronic and R. Sierpe}, url = {/brokenurl#<Go to ISI>://WOS:000412754400038}, doi = {10.1371/journal.pone.0185652}, issn = {1932-6203}, year = {2017}, date = {2017-01-01}, journal = {Plos One}, volume = {12}, number = {10}, abstract = {While 2-amino-4-(4-chlorophenyl)thiazole (AT) drug and thiazole derivatives have several biological applications, these compounds present some drawbacks, such as low aqueous solubility and instability. A new complex of beta CD-AT has been synthesized to increase AT solubility and has been used as a substrate for the deposit of solid-state AuNPs via magnetron sputtering, thus forming the beta CD-AT-AuNPs ternary system, which is stable in solution. Complex formation has been confirmed through powder X-ray diffraction and 1D and 2D nuclear magnetic resonance. Importantly, the amine and sulfide groups of AT remained exposed and can interact with the surfaces of the AuNPs. The complex association constant (970 M-1) has been determined using phase solubility analysis. AuNPs formation (32 nm average diameter) has been studied by UV-Visible spectroscopy, transmission/scanning electron microscopy and energy-dispersive X-ray analysis. The in vitro permeability assays show that effective permeability of AT increased using beta CD. In contrast, the ternary system did not have the capacity to diffuse through the membrane. Nevertheless, the antibacterial assays have demonstrated that AT is transferred from beta CD-AT-AuNPs, being available to exert its antibacterial activity. In conclusion, this novel beta CD-AT-AuNPs ternary system is a promising alternative to improve the delivery of AT drugs in therapy.}, keywords = {activity, beta-cyclodextrin, complexes, delivery-systems, inclusion organophosphorus pesticides, photodegradation rates, thiazoles}, pubstate = {published}, tppubtype = {article} } While 2-amino-4-(4-chlorophenyl)thiazole (AT) drug and thiazole derivatives have several biological applications, these compounds present some drawbacks, such as low aqueous solubility and instability. A new complex of beta CD-AT has been synthesized to increase AT solubility and has been used as a substrate for the deposit of solid-state AuNPs via magnetron sputtering, thus forming the beta CD-AT-AuNPs ternary system, which is stable in solution. Complex formation has been confirmed through powder X-ray diffraction and 1D and 2D nuclear magnetic resonance. Importantly, the amine and sulfide groups of AT remained exposed and can interact with the surfaces of the AuNPs. The complex association constant (970 M-1) has been determined using phase solubility analysis. AuNPs formation (32 nm average diameter) has been studied by UV-Visible spectroscopy, transmission/scanning electron microscopy and energy-dispersive X-ray analysis. The in vitro permeability assays show that effective permeability of AT increased using beta CD. In contrast, the ternary system did not have the capacity to diffuse through the membrane. Nevertheless, the antibacterial assays have demonstrated that AT is transferred from beta CD-AT-AuNPs, being available to exert its antibacterial activity. In conclusion, this novel beta CD-AT-AuNPs ternary system is a promising alternative to improve the delivery of AT drugs in therapy. |
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. |
2015 |
Sierpe, R; Lang, E; Jara, P; Guerrero, A R; Chornik, B; Kogan, M J; Yutronic, N Gold Nanoparticles Interacting with Beta-Cyclodextrin-Phenylethylamine Inclusion Complex: A Ternary System for Photothermal Drug Release Artículo de revista Acs Applied Materials & Interfaces, 7 (28), pp. 15177-15188, 2015, ISSN: 1944-8244. Resumen | Enlaces | BibTeX | Etiquetas: applications, beta-cyclodextrin, biomedical brain complex, delivery, effect, enhanced gold inclusion laser-ablation, magnetron nanoparticles, permeability, phenylethylamine, photothermal plasmon resonance, retention, silver size, sputtering, surface @article{RN249, title = {Gold Nanoparticles Interacting with Beta-Cyclodextrin-Phenylethylamine Inclusion Complex: A Ternary System for Photothermal Drug Release}, author = { R. Sierpe and E. Lang and P. Jara and A.R. Guerrero and B. Chornik and M.J. Kogan and N. Yutronic}, url = {/brokenurl#<Go to ISI>://WOS:000358558300010}, doi = {10.1021/acsami.5b00186}, issn = {1944-8244}, year = {2015}, date = {2015-01-01}, journal = {Acs Applied Materials & Interfaces}, volume = {7}, number = {28}, pages = {15177-15188}, abstract = {We report the synthesis of a 1:1 beta-cydodextrin-phenylethylamine (beta CD-PhEA) inclusion complex (IC) and the adhesion of gold nanoparticles (AuNPs) onto micro crystals of this complex, which forms a ternary system. The formation of the IC was confirmed by powder X-ray diffraction and NMR analyses (H-1 and ROESY). The stability constant of the IC (760 M-1) was determined using the phase solubility method. The adhesion of AuNPs was obtained using the magnetron sputtering technique, and the presence of AuNPs was confirmed using UV-vis spectroscopy (surface plasmon resonance effect), which showed. an absorbance at 533 nm. The powder X-ray diffractograms of beta CD-PhEA were similar to those of the crystals decorated with AuNPs. A comparison of the one- and two-dimensional NMR spectra of the IC with and without AuNPs suggests partial displacement of the guest to the outside of the beta CD due to attraction toward AuNPs, a characteristic tropism effect. The size, morphology, and distribution of the AuNPs were analyzed using TEM and SEM. The average size of the AuNPs was 14 nm. Changes in the IR and Raman spectra were attributed to the formation of the complex and to the specific interactions of this group with the AuNPs. Laser irradiation assays show that the ternary system beta CD-PhEA-AuNPs in solution enables the release of the guest.}, keywords = {applications, beta-cyclodextrin, biomedical brain complex, delivery, effect, enhanced gold inclusion laser-ablation, magnetron nanoparticles, permeability, phenylethylamine, photothermal plasmon resonance, retention, silver size, sputtering, surface}, pubstate = {published}, tppubtype = {article} } We report the synthesis of a 1:1 beta-cydodextrin-phenylethylamine (beta CD-PhEA) inclusion complex (IC) and the adhesion of gold nanoparticles (AuNPs) onto micro crystals of this complex, which forms a ternary system. The formation of the IC was confirmed by powder X-ray diffraction and NMR analyses (H-1 and ROESY). The stability constant of the IC (760 M-1) was determined using the phase solubility method. The adhesion of AuNPs was obtained using the magnetron sputtering technique, and the presence of AuNPs was confirmed using UV-vis spectroscopy (surface plasmon resonance effect), which showed. an absorbance at 533 nm. The powder X-ray diffractograms of beta CD-PhEA were similar to those of the crystals decorated with AuNPs. A comparison of the one- and two-dimensional NMR spectra of the IC with and without AuNPs suggests partial displacement of the guest to the outside of the beta CD due to attraction toward AuNPs, a characteristic tropism effect. The size, morphology, and distribution of the AuNPs were analyzed using TEM and SEM. The average size of the AuNPs was 14 nm. Changes in the IR and Raman spectra were attributed to the formation of the complex and to the specific interactions of this group with the AuNPs. Laser irradiation assays show that the ternary system beta CD-PhEA-AuNPs in solution enables the release of the guest. |
2017 |
Gold Nanoparticles Stabilized with Beta Cyclodextrin-2-Amino-4-(4-Chlorophenyl)Thiazole Complex: A Novel System for Drug Transport Artículo de revista Plos One, 12 (10), 2017, ISSN: 1932-6203. |
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. |
2015 |
Gold Nanoparticles Interacting with Beta-Cyclodextrin-Phenylethylamine Inclusion Complex: A Ternary System for Photothermal Drug Release Artículo de revista Acs Applied Materials & Interfaces, 7 (28), pp. 15177-15188, 2015, ISSN: 1944-8244. |