We report the synthesis of a 1:1 β-cyclodextrin-phenylethylamine (βCD-PhEA) inclusion complex (IC) and the adhesion of gold nanoparticles (AuNPs) onto microcrystals of this complex, which forms a ternary system. The formation of the IC was confirmed by powder X-ray diffraction and NMR analyses ((1)H 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 βCD-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 βCD 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 βCD-PhEA-AuNPs in solution enables the release of the guest.
This article describes the sorption properties of cyclodextrin polymers (nanosponges; NS) with the pesticides 4-chlorophenoxyacetic acid (4-CPA) and 2,3,4,6-tetrachlorophenol (TCF), including an evaluation of its efficiency and a comparison with other materials, such as granulated activated carbon (GAC). NS-pesticide complexes were characterized by scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), X-ray powder diffraction (XRPD), proton nuclear magnetic resonance (1H-NMR), UV–VIS, and thermogravimetric analysis (TGA). This confirms the interactions of the guests with nanosponges and shows that the polymers have favorable sorption capacities for chlorinated aromatic guests. Our studies also show that the inclusion complex is predominantly favored for NS/CPA rather than those formed between TCF and NS due to the size of the adsorbate and steric effects. Sorption studies carried with repeated cycles demonstrate that NS polymers could be an improved technology for pollutant removal from aquatic environments, as they are very efficient and reusable materials. Our experiments and characterization by SEM, EDS, UV–VIS, and magnetization saturation (VSM) also show that NS is an optimal substrate for the deposition of magnetite nanoparticles, thus improving the usefulness and properties of the polymer, as the nanosponges could be retrieved from aqueous solution with a neodymium magnet without losing its efficiency as a pesticide sorbent.
In drug delivery, one widely used way of overcoming the biopharmaceutical problems present in several active pharmaceutical ingredients, such as poor aqueous solubility, early instability, and low bioavailability, is the formation of inclusion compounds with cyclodextrins (CD). In recent years, the use of CD derivatives in combination with nanomaterials has shown to be a promising strategy for formulating new, optimized systems. The goals of this review are to give in-depth knowledge and critical appraisal of the main CD-modified or CD-based nanomaterials for drug delivery, such as lipid-based nanocarriers, natural and synthetic polymeric nanocarriers, nanosponges, graphene derivatives, mesoporous silica nanoparticles, plasmonic and magnetic nanoparticles, quantum dots and other miscellaneous systems such as nanovalves, metal-organic frameworks, Janus nanoparticles, and nanofibers. Special attention is given to nanosystems that achieve controlled drug release and increase their bioavailability during in vivo studies.
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 βCD-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 βCD-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 βCD. 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 βCD-AT-AuNPs, being available to exert its antibacterial activity. In conclusion, this novel βCD-AT-AuNPs ternary system is a promising alternative to improve the delivery of AT drugs in therapy.
An ordered self-assembly of gold nanoparticles (AuNPs) onto microcrystal faces of a 2a-cyclodextrin-dodecanethiol (2aCD-DDT) inclusion compound (IC) by means of a magnetron sputtering technique was obtained. The preferential deposition on the (001) plane of the aCD IC crystal occurs because -SH groups from the guest molecules found within the aCD protrude into that plane. These -SH groups form a two-dimensional hexagonal lattice that interacts with the metal NPs, arranging them in an ordered way.
This article describes the use of β-cyclodextrin-based carbonate nanosponges (NSs) decorated with superparamagnetic Fe3O4 nanoparticles to study and investigate the potential removal of dinotefuran (DTF) from wastewater. The NS-DTF inclusion compound was characterized by transmission electron microscopy (TEM), energy-dispersive spectroscopy (EDS), UV-visible spectroscopy (UV-VIS), scanning electron microscopy (SEM), thermogravimetric analysis (TGA), X-ray powder diffraction (XRPD) and proton nuclear magnetic resonance (1H-NMR). The adsorption efficiency of NSs was evaluated as function of different contact times. The results confirmed that the NSs have a favourable sorption capacity for the chosen guest, as the polymers exhibited a maximum adsorption of 4.53 × 10−3 mmol/g for DTF. We also found that magnetic NSs show good reusability as they maintain their efficiency after eight adsorption and desorption cycles. Our studies and characterization by means of SEM, TEM, EDS, vibrating sample magnetometer (VSM) and UV-VIS also show that NSs with magnetic properties are excellent tools for insecticide removal from aqueous environments.
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