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1.
Pestic Biochem Physiol ; 202: 105917, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38879319

RESUMO

Owing to their beneficial functional capabilities, essential oils were largely used. However, their low aqueous solubility, instability, and high volatility urged scientists to their encapsulation with cyclodextrins (CDs) to tackle their shortcomings. In this study, the co-precipitation method was used to prepare ß-CD/Eucalyptus globulus essential oil (EGEO) inclusion complexes (ICs). ß-CD/EGEO ICs were prepared at ratios (w:w) 1:2 and 1:4 with an encapsulation efficiency of 93 and 96%, respectively. The ICs characterization using the Fourier transform Infrared spectroscopy, differential scanning calorimetry, X-ray powder diffraction, Dynamic Light Scattering, and Laser Doppler Velocimetry confirmed the formation of ß-CD/EGEO ICs. The insecticidal activity of the free EGEO and ICs was explored and displayed that the complex ß-CD/EGEO 1:4 had the highest activity with the lowest LC50 against Ephestia kuehniella larvae (5.03 ± 1.16 mg/g) when compared to the free oil (8.38 ± 1.95 mg/g). Molecular docking simulations stipulated that the compound α-Bisabolene epoxide had the best docking score (ΔG = -7.4 Kcal/mol) against the selected insecticidal target α-amylase. Additionally, toxicity evaluation of the studied essential oil suggested that it could be safely used as a potent bioinsecticide as compared to chemical insecticides. This study reveals that the formation of ß-CD/EGEO ICs enhanced the oil activity and stability and could be a promising and safe tool to boost its application in food or pharmaceutical fields.


Assuntos
Eucalyptus , Inseticidas , Larva , Simulação de Acoplamento Molecular , Óleos Voláteis , beta-Ciclodextrinas , Animais , Inseticidas/química , Inseticidas/farmacologia , Larva/efeitos dos fármacos , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Eucalyptus/química , beta-Ciclodextrinas/química , beta-Ciclodextrinas/farmacologia , Besouros/efeitos dos fármacos , Espectroscopia de Infravermelho com Transformada de Fourier , Difração de Raios X
2.
ACS Appl Mater Interfaces ; 16(24): 30900-30914, 2024 Jun 19.
Artigo em Inglês | MEDLINE | ID: mdl-38848495

RESUMO

Coumarins have great pharmacotherapeutic potential, presenting several biological and pharmaceutical applications, like antibiotic, fungicidal, anti-inflammatory, anticancer, anti-HIV, and healing activities, among others. These molecules are practically insoluble in water, and for biological applications, it became necessary to complex them with cyclodextrins (CDs), which influence their bioavailability in the target organism. In this work, we studied two coumarins, and it was possible to conclude that there were structural differences between 4,7-dimethyl-2H-chromen-2-one (DMC) and 7-methoxy-4-methyl-2H-chromen-2-one (MMC)/ß-CD that were solubilized in ethanol, frozen, and lyophilized (FL) and the mechanical mixtures (MM). In addition, the inclusion complex formation improved the solubility of DMC and MMC in an aqueous medium. According to the data, the inclusion complexes were formed and are more stable at a molar ratio of 2:1 coumarin/ß-CD, and hydrogen bonds along with π-π stacking interactions are responsible for the better stability, especially for (MMC)2@ß-CD. In vivo wound healing studies in mice showed faster re-epithelialization and the best deposition of collagen with the (DMC)2@ß-CD (FL) and (MMC)2@ß-CD (FL) inclusion complexes, demonstrating clearly that they have potential in wound repair. Therefore, (DMC)2@ß-CD (FL) deserves great attention because it presented excellent results, reducing the granulation tissue and mast cell density and improving collagen remodeling. Finally, the protein binding studies suggested that the anti-inflammatory activities might exert their biological function through the inhibition of MEK, providing the possibility of development of new MEK inhibitors.


Assuntos
Cumarínicos , Cicatrização , beta-Ciclodextrinas , beta-Ciclodextrinas/química , Cumarínicos/química , Cumarínicos/farmacologia , Animais , Cicatrização/efeitos dos fármacos , Camundongos , Humanos , Solubilidade , Masculino
3.
Int J Mol Sci ; 25(11)2024 May 28.
Artigo em Inglês | MEDLINE | ID: mdl-38892075

RESUMO

Cyclodextrins (CDs) are cyclic oligosaccharides able to form noncovalent water-soluble complexes useful in many different applications for the solubilization, delivery, and greater bioavailability of hydrophobic drugs. The complexation of 5-fluorouracil (5-FU) with natural or synthetic cyclodextrins permits the solubilization of this poorly soluble anticancer drug. In this theoretical work, the complexes between ß-CD and 5-FU are investigated using molecular mechanics (MM) and molecular dynamics (MD) simulations in water. The inclusion complexes are formed thanks to the favorable intermolecular interactions between ß-CD and 5-FU. Both 1:1 and 1:2 ß-CD/5-FU stoichiometries are investigated, providing insight into their interaction geometries and stability over time in water. In the 1:2 ß-CD/5-FU complexes, the intermolecular interactions affect the drug's mobility, suggesting a two-step release mechanism: a fast release for the more exposed and hydrated drug molecule, with greater freedom of movement near the ß-CD rims, and a slow one for the less-hydrated and well-encapsulated and confined drug. MD simulations study the intermolecular interactions between drugs and specific carriers at the atomistic level, suggesting a possible release mechanism and highlighting the role of the impact of the drug concentration on the kinetics process in water. A comparison with experimental data in the literature provides further insights.


Assuntos
Fluoruracila , Interações Hidrofóbicas e Hidrofílicas , Simulação de Dinâmica Molecular , Água , beta-Ciclodextrinas , Fluoruracila/química , beta-Ciclodextrinas/química , Água/química , Solubilidade
4.
J Sep Sci ; 47(12): e2400190, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38894562

RESUMO

An efficient method for the continuous separation of Voriconazole enantiomers was developed using sulfobutyl ether-ß-cyclodextrin (SBE-ß-CD) as a chiral selector in high-speed countercurrent chromatography (HSCCC) with different types. The separation was performed using a two-phase solvent system consisting of n-hexane/ethyl acetate/100 mmol/L phosphate buffer solution (pH = 3.0, containing 50 mmol/L SBE-ß-CD) (1.5:0.5:2, v/v/v). A fast and predictable scale-up process was achieved using an analytical DE HSCCC instrument. The optimized parameters were subsequently applied to a preparative Tauto HSCCC instrument, resulting in consistent separation time and enantiomeric purity, with throughput boosted by a remarkable 11-fold. Preparative HSCCC successfully separated 506 mg of the racemate, delivering enantiomers exceeding 99% purity as confirmed by high-performance liquid chromatography analysis. This investigation presents an effective methodology for forecasting the HSCCC scale-up process and attaining continuous separation of chiral drugs.


Assuntos
Distribuição Contracorrente , Voriconazol , Distribuição Contracorrente/métodos , Estereoisomerismo , Voriconazol/química , Voriconazol/isolamento & purificação , Cromatografia Líquida de Alta Pressão , beta-Ciclodextrinas/química
5.
Carbohydr Polym ; 339: 122253, 2024 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-38823920

RESUMO

In vitro tumor models are essential for understanding tumor behavior and evaluating tumor biological properties. Hydrogels that can mimic the tumor extracellular matrix have become popular for creating 3D in vitro tumor models. However, designing biocompatible hydrogels with appropriate chemical and physical properties for constructing tumor models is still a challenge. In this study, we synthesized a series of ß-cyclodextrin (ß-CD)-crosslinked polyacrylamide hydrogels with different ß-CD densities and mechanical properties and evaluated their potential for use in 3D in vitro tumor model construction, including cell capture and spheroid formation. By utilizing a combination of ß-CD-methacrylate (CD-MA) and a small amount of N,N'-methylene bisacrylamide (BIS) as hydrogel crosslinkers and optimizing the CD-MA/BIS ratio, the hydrogels performed excellently for tumor cell 3D culture and spheroid formation. Notably, when we co-cultured L929 fibroblasts with HeLa tumor cells on the hydrogel surface, co-cultured spheroids were formed, showing that the hydrogel can mimic the complexity of the tumor extracellular matrix. This comprehensive investigation of the relationship between hydrogel mechanical properties and biocompatibility provides important insights for hydrogel-based in vitro tumor modeling and advances our understanding of the mechanisms underlying tumor growth and progression.


Assuntos
Resinas Acrílicas , Hidrogéis , Esferoides Celulares , beta-Ciclodextrinas , Esferoides Celulares/efeitos dos fármacos , Humanos , Resinas Acrílicas/química , Resinas Acrílicas/farmacologia , Hidrogéis/química , Hidrogéis/farmacologia , Hidrogéis/síntese química , beta-Ciclodextrinas/química , beta-Ciclodextrinas/farmacologia , Células HeLa , Animais , Camundongos , Reagentes de Ligações Cruzadas/química , Materiais Biocompatíveis/química , Materiais Biocompatíveis/farmacologia , Técnicas de Cultura de Células em Três Dimensões/métodos , Metacrilatos/química , Técnicas de Cocultura , Neoplasias/patologia
6.
Nat Commun ; 15(1): 4787, 2024 Jun 05.
Artigo em Inglês | MEDLINE | ID: mdl-38839843

RESUMO

Pure organic phosphorescence resonance energy transfer is a research hotspot. Herein, a single-molecule phosphorescence resonance energy transfer system with a large Stokes shift of 367 nm and near-infrared emission is constructed by guest molecule alkyl-bridged methoxy-tetraphenylethylene-phenylpyridines derivative, cucurbit[n]uril (n = 7, 8) and ß-cyclodextrin modified hyaluronic acid. The high binding affinity of cucurbituril to guest molecules in various stoichiometric ratios not only regulates the topological morphology of supramolecular assembly but also induces different phosphorescence emissions. Varying from the spherical nanoparticles and nanorods for binary assemblies, three-dimensional nanoplate is obtained by the ternary co-assembly of guest with cucurbit[7]uril/cucurbit[8]uril, accompanying enhanced phosphorescence at 540 nm. Uncommonly, the secondary assembly of ß-cyclodextrin modified hyaluronic acid and ternary assembly activates a single intramolecular phosphorescence resonance energy transfer process derived from phenyl pyridines unit to methoxy-tetraphenylethylene function group, enabling a near-infrared delayed fluorescence at 700 nm, which ultimately applied to mitochondrial targeted imaging for cancer cells.


Assuntos
Transferência Ressonante de Energia de Fluorescência , Ácido Hialurônico , Imidazóis , beta-Ciclodextrinas , beta-Ciclodextrinas/química , Humanos , Ácido Hialurônico/química , Imidazóis/química , Transferência Ressonante de Energia de Fluorescência/métodos , Hidrocarbonetos Aromáticos com Pontes/química , Nanopartículas/química , Estilbenos/química , Piridinas/química , Células HeLa , Nanotubos/química , Mitocôndrias/metabolismo , Compostos Heterocíclicos com 2 Anéis , Compostos Macrocíclicos , Imidazolidinas
7.
Zhongguo Ying Yong Sheng Li Xue Za Zhi ; 40: e20240002, 2024 Jun 12.
Artigo em Inglês | MEDLINE | ID: mdl-38862271

RESUMO

OBJECTIVE: Raloxifene hydrochloride (RLX) is used extensively in the treatment of osteoporosis, only 2% of RLX's bioavailability remains after a significant first pass metabolism. Besides coming from BCS class II, RLX is not very soluble in water. Thus, the goal of the current study was to improve RLX solubility by creating an inclusion complex using ß cyclodextrin (ß-CD) as a carrier and solid dispersion with Poloxamer 407. METHODS: Inclusion complex and solid dispersion were made using a variety of techniques, including kneading, co-precipitation, and physical mixing and solid dispersion using different drug to carrier ratios (1:1, 1:2 and 1:3). RESULTS: Inclusion complex made using the co-precipitation method had shown 9-fold improvements in water solubility when compared with plain RLX. In order to assess the optimized complex's compatibility, thermal analysis, and crystallinity, X-ray diffraction, differential scanning calorimetry, and Fourier transform infrared spectroscopy were used. The XRD and DSC study's results indicated that RLX changed from a crystalline to an amorphous state. IC-6 exhibits effective water solubility based on the outcome. However, upon comparison of the two techniques, the ß-CD complexation method shown an impressive rise in drug solubility when compared to solid dispersion.


Assuntos
Disponibilidade Biológica , Cloridrato de Raloxifeno , Solubilidade , beta-Ciclodextrinas , Cloridrato de Raloxifeno/química , Cloridrato de Raloxifeno/farmacocinética , beta-Ciclodextrinas/química , Animais , Poloxâmero/química , Portadores de Fármacos/química
8.
AAPS PharmSciTech ; 25(5): 135, 2024 Jun 11.
Artigo em Inglês | MEDLINE | ID: mdl-38862657

RESUMO

Lutein (Lut) is a recognized nutritional supplement known for its antioxidative and anti-inflammatory properties, crucial in mitigating ocular disease. However, enhancements to Lut stability and solubility remain challenges to be addressed in the healthcare industry. Herein, we fabricated and evaluated a food-grade highly porous ß-cyclodextrin metal-organic framework (ß-CD-MOF) for its ability to encapsulate Lut. Lut stability considerably improved when loaded into ß-CD-MOF to form a Lut@ß-CD-MOF complex, which exhibited better stability than Lut loaded into the γ-cyclodextrin metal-organic framework (Lut@γ-CD-MOF), Lut@ß-CD, and commercial product (Blackmores™) at 40°C, 60°C, and 70°C, respectively. The solubility of Lut@ß-CD-MOF in water increased by 26.8-fold compared to raw Lut at 37°C. Lut@ß-CD-MOF exhibited greater hydrophilicity, as determined by measuring the water contact angle. Molecular docking and other characterizations of Fourier transform infrared spectroscopy and powder X-ray diffraction confirmed that Lut was successfully encapsulated in the chamber formed by the three cyclodextrins in ß-CD-MOF. Thermogravimetric analysis and Raman spectroscopy demonstrated that Lut distributed in the ß-CD-MOF cavity deeply improved Lut stability and solubility. In conclusion, our findings underscored the function of ß-CD-MOF in enhancing Lut stability and solubility for formulation applications.


Assuntos
Luteína , Estruturas Metalorgânicas , Solubilidade , beta-Ciclodextrinas , Estruturas Metalorgânicas/química , beta-Ciclodextrinas/química , Luteína/química , Estabilidade de Medicamentos , Difração de Raios X/métodos , Simulação de Acoplamento Molecular/métodos , Espectroscopia de Infravermelho com Transformada de Fourier/métodos , Interações Hidrofóbicas e Hidrofílicas , Porosidade
9.
AAPS PharmSciTech ; 25(5): 134, 2024 Jun 11.
Artigo em Inglês | MEDLINE | ID: mdl-38862663

RESUMO

Inclusion complexes require higher concentration of Beta cyclodextrins (ßCD) resulting in increased formulation bulk, toxicity, and production costs. This systematic review offers a comprehensive analysis using Quality by design (QbD) as a tool to predict potential applications of Polyvinylpyrrolidone (PVP) as a ternary substance to address issues of inclusion complexes. We reviewed 623 documents from 2013 to 2023 and Eighteen (18) research papers were selected for statistical and meta-analysis using the QbD concept to identify the most critical factors for selecting drugs and effect of PVP on inclusion complexes. The QbD analysis revealed that Molecular weight (MW), Partition coefficient (Log P), and the auxiliary substance ratio directly affected complexation efficiency (CE), thermodynamic stability in terms of Gibbs free energy (ΔG), and percent drug release. However, Stability constant (Ks) remained unaffected by any of these parameters. The results showed that low MW (250), median Log P (6), and a ßCD: PVP ratio of 2:3 would result in higher CE, lower G, and improved drug release. PVP improves drug solubility, enhances delivery and therapeutic outcomes, and counteracts increased drug ionization due to decreased pH. In certain cases, its bulky nature and hydrogen bonding with CD molecules can form non-inclusion complexes. The findings of the study shows that there is potential molecular interaction between PVP and ß-cyclodextrins, which possibly enhances the stability of inclusion complexes for drug with low MW and log P values less than 9. The systematic review shows a comprehensive methodology based on QbD offers a replicable template for future investigations into drug formulation research.


Assuntos
Ciclodextrinas , Povidona , Solubilidade , beta-Ciclodextrinas , beta-Ciclodextrinas/química , Química Farmacêutica/métodos , Ciclodextrinas/química , Liberação Controlada de Fármacos , Excipientes/química , Peso Molecular , Projetos Piloto , Povidona/química , Termodinâmica
10.
Carbohydr Polym ; 340: 122328, 2024 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-38857995

RESUMO

This article presents a novel approach to treating prostate cancer using a nanocarrier composed of folic acid (FA), ß-cyclodextrin (ß-CD), and magnetic graphene oxide (MGO) as a theranostic agent. The carrier is designed to improve the solubility and bioavailability of curcumin, a potential therapeutic substance against prostate cancer. Folic acid receptors overexpressed on the surface of solid tumors, including prostate cancer, may facilitate targeted drug delivery to tumor cells while avoiding nonspecific effects on healthy tissues. The anticancer efficacy of Folic acid-curcumin@ß-CD-MGO in vitro was also examined on LNCaP (an androgen-dependent) and PC3 (an androgen-independent) prostate cancer cells. The relaxivity of nanoparticles in MRI images was also investigated as a diagnostic factor. The results showed a concentration-dependent inhibitory effect on cell proliferation, induction of oxidative damage, and apoptotic effects. Also, nanoparticle relaxometry shows that this agent can be used as a negative contrast agent in MRI images. Overall, this study represents a promising theranostic agent to improve the delivery and trace of curcumin and enhance its therapeutic potential in the treatment of prostate cancer.


Assuntos
Proliferação de Células , Curcumina , Ácido Fólico , Grafite , Neoplasias da Próstata , Nanomedicina Teranóstica , beta-Ciclodextrinas , Curcumina/química , Curcumina/farmacologia , Masculino , Grafite/química , Grafite/farmacologia , Humanos , Neoplasias da Próstata/tratamento farmacológico , Neoplasias da Próstata/diagnóstico por imagem , Neoplasias da Próstata/patologia , beta-Ciclodextrinas/química , Nanomedicina Teranóstica/métodos , Ácido Fólico/química , Ácido Fólico/farmacologia , Proliferação de Células/efeitos dos fármacos , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Antineoplásicos/farmacologia , Antineoplásicos/química , Portadores de Fármacos/química , Imageamento por Ressonância Magnética/métodos , Nanopartículas/química , Receptores de Folato com Âncoras de GPI/metabolismo , Liberação Controlada de Fármacos , Nanopartículas de Magnetita/química
11.
Carbohydr Polym ; 340: 122306, 2024 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-38858025

RESUMO

In this study, a novel hydrogel, ß-cyclodextrin/carbon dots-grafted cellulose nanofibrils hydrogel (ßCCH), was fabricated for removal and fluorescence determination of levofloxacin (LEV). A comprehensive analysis was performed to characterize its physicochemical properties. Batch adsorption experiments were conducted, revealing that ßCCH reached a maximum adsorption capacity of 1376.9 mg/g, consistent with both Langmuir and pseudo-second-order models, suggesting that the adsorption process of LEV on ßCCH was primarily driven by chemical adsorption. The removal efficiency of ßCCH was 99.2 % under the fixed conditions (pH: 6, initial concentration: 20 mg/L, contact time: 300 min, temperature: 25 °C). The removal efficiency of ßCCH for LEV still achieved 97.3 % after five adsorption-desorption cycles. By using ßCCH as a fluorescent probe for LEV, a fast and sensitive method was established with linear ranges of 1-120 mg/L and 0.2-1.0 µg/L and a limit of detection (LOD) as low as 0.09 µg/L. The viability of ßCCH was estimated based on the economic analysis of the synthesis process and the removal of LEV, demonstrating that ßCCH was more cost-effective than commercial activated carbon. This study provides a novel approach for preparing a promising antibiotic detection and adsorption material with the advantages of stability, and cost-effectiveness.


Assuntos
Carbono , Celulose , Hidrogéis , Levofloxacino , Nanofibras , beta-Ciclodextrinas , Levofloxacino/análise , Levofloxacino/química , beta-Ciclodextrinas/química , Celulose/química , Adsorção , Nanofibras/química , Carbono/química , Hidrogéis/química , Antibacterianos/análise , Antibacterianos/química , Limite de Detecção , Poluentes Químicos da Água/análise , Corantes Fluorescentes/química , Pontos Quânticos/química , Fluorescência
12.
Biomacromolecules ; 25(6): 3685-3702, 2024 Jun 10.
Artigo em Inglês | MEDLINE | ID: mdl-38779908

RESUMO

Combination therapy has emerged as a promising approach for treating tumors, although there is room for improvement. This study introduced a novel strategy that combined the enhancement of apoptosis, ferroptosis, and DNA damage to improve therapeutic outcomes for prostate cancer. Specifically, we have developed a supramolecular oxidative stress nanoamplifier, which was comprised of ß-cyclodextrin, paclitaxel, and ferrocene-poly(ethylene glycol). Paclitaxel within the system disrupted microtubule dynamics, inducing G2/M phase arrest and apoptosis. Concurrently, ferrocene utilized hydrogen peroxide to generate toxic hydroxyl radicals in cells through the Fenton reaction, triggering a cascade of reactive oxygen species expansion, reduction of glutathione levels, lipid peroxidation, and ferroptosis. The increased number of hydroxyl radicals and the inhibitory effect of THZ531 on DNA repair mechanisms exacerbated DNA damage within tumor cells. As expected, the supramolecular nanoparticles demonstrated excellent drug delivery ability to tumor cells or tissues, exhibited favorable biological safety in vivo, and enhanced the killing effect on prostate cancer.


Assuntos
Estresse Oxidativo , Paclitaxel , Neoplasias da Próstata , Paclitaxel/farmacologia , Paclitaxel/química , Humanos , Masculino , Estresse Oxidativo/efeitos dos fármacos , Animais , Neoplasias da Próstata/tratamento farmacológico , Neoplasias da Próstata/metabolismo , Neoplasias da Próstata/patologia , Camundongos , Metalocenos/química , Nanopartículas/química , Apoptose/efeitos dos fármacos , Compostos Ferrosos/química , Compostos Ferrosos/farmacologia , Linhagem Celular Tumoral , beta-Ciclodextrinas/química , Polietilenoglicóis/química , Camundongos Nus , Ferroptose/efeitos dos fármacos , Espécies Reativas de Oxigênio/metabolismo , Dano ao DNA/efeitos dos fármacos
13.
J Chromatogr A ; 1728: 464991, 2024 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-38788322

RESUMO

The abnormal estrogens levels in human body can cause many side effects and diseases, but the quantitative detection of the trace estrogens in complex biological samples still remains great challenge. Here we reported the fabrication of a novel core-shell structured magnetic cyclodextrin microporous organic network (Fe3O4@CD-MON) for rapid magnetic solid phase extraction (MSPE) of four estrogens in human serum and urine samples prior to HPLC-UV determination. The uniform spherical core-shell Fe3O4@CD-MONs was successfully regulated by altering the reactive monomers and solvents. The Fe3O4@CD-MONs owned high specific surface area, good hydrophobicity, large superparamagnetism, and abundant extraction sites for estrogens. Under optimal conditions, the proposed MSPE-HPLC-UV method provided wide linearity range (2.0-400 µg L-1), low limits of detection (0.5-1.0 µg L-1), large enrichment factors (183-198), less adsorbent consumption (3 mg), short extraction time (3 min), and good stability and reusability (at least 8 cycles). The established method had also been successfully applied to the enrichment and detection of four estrogens in serum and urine samples with a recovery of 88.4-105.1 % and a relative standard deviation of 1.0-5.9 %. This work confirmed the feasibility of solvent and monomer regulation synthesis of Fe3O4@CD-MON composites, and revealed the great prospects of magnetic CD-MONs for efficient enrichment of trace estrogens in complex biological samples.


Assuntos
Estrogênios , Limite de Detecção , Extração em Fase Sólida , beta-Ciclodextrinas , Humanos , Cromatografia Líquida de Alta Pressão/métodos , Estrogênios/urina , Estrogênios/sangue , Estrogênios/isolamento & purificação , Estrogênios/análise , Estrogênios/química , Extração em Fase Sólida/métodos , beta-Ciclodextrinas/química , Solventes/química , Porosidade , Nanopartículas de Magnetita/química , Adsorção
14.
Spectrochim Acta A Mol Biomol Spectrosc ; 318: 124493, 2024 Oct 05.
Artigo em Inglês | MEDLINE | ID: mdl-38796891

RESUMO

6-mercaptopurine (6-MP) is widely used in the treatment of many diseases, but exhibits some serious side effects due to its toxicity. Therefore, it is important and imperative to effectively control and monitoring concentration of 6-MP. Herein, we designed a smartphone-assisted colorimetric sensing platform for 6-MP detection, based on an excellent ß-cyclodextrin modified MnO2 nanosheets (ß-CD@MnO2 NNS) mediated oxidase-like activity. ß-CD@MnO2 NNS can directly oxidizes 3,3',5,5'-tetramethylbenzidine (TMB) into oxidized TMB with color changes, yielding more than 3-fold higher oxidase-like catalytic activity compared with individual MnO2 NNS. After adding 6-MP, ß-CD@MnO2 NNS can be reduced to Mn2+ and lose their oxidase-like properties, resulting in a color and absorbance change for sensitive and selectivity detection of 6-MP. Meanwhile, the smartphone-based color recognition application can intuitively and simply measure the concentration of 6-MP. The limits of detection UV-vis instrument and smartphone were 0.35 µM and 0.86 µM, respectively. This method has also been successfully applied to the detection of real samples. Finally, this study provides a new promising platform for detection of 6-MP and is expected to be used in application of pharmaceutical analysis and biomedicine.


Assuntos
Colorimetria , Compostos de Manganês , Mercaptopurina , Nanoestruturas , Óxidos , Smartphone , beta-Ciclodextrinas , Colorimetria/métodos , Compostos de Manganês/química , beta-Ciclodextrinas/química , Óxidos/química , Mercaptopurina/análise , Nanoestruturas/química , Oxirredutases/metabolismo , Oxirredutases/química , Limite de Detecção , Humanos , Benzidinas/química
15.
J Chromatogr A ; 1728: 465032, 2024 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-38815479

RESUMO

Molecularly imprinted polymer with water-compatibility for effective separation and enrichment of targeted trace pollutants from complicated matrix has captured extensive attention in terms of their high selectivity and matrix compatibility. This study focuses on modified ß-cyclodextrin is used as a hydrophilic functional monomer to develop magnetic molecularly imprinted polymers (MMIPs). MMIPs were prepared using Fe3O4 nanoparticles as carriers and bisphenol A (BPA) as templates using a two-step fixation strategy and surface imprinting technology. The structural characteristic and binding properties of the prepared MMIPs were thoroughly studied. The MMIPs exhibited high crystallinity, high adsorption capacity, fast rebinding rate, remarkable selectivity and distinguish reusability. In addition, through magnetic solid-phase extraction separation technology and high-performance liquid chromatography ultraviolet quantitative detection technology, MMIPs are used for selective enrichment and detection of BPA in complex media such as environmental water and milk. This work provides a new route to construct the hydrophilic molecularly imprinted materials and a new sight on developing more effective sample pretreatment strategies for monitoring targeted pollution in complicated aqueous media.


Assuntos
Compostos Benzidrílicos , Interações Hidrofóbicas e Hidrofílicas , Polímeros Molecularmente Impressos , Fenóis , Extração em Fase Sólida , Poluentes Químicos da Água , Compostos Benzidrílicos/análise , Compostos Benzidrílicos/química , Fenóis/análise , Fenóis/química , Polímeros Molecularmente Impressos/química , Extração em Fase Sólida/métodos , Adsorção , Cromatografia Líquida de Alta Pressão/métodos , Poluentes Químicos da Água/análise , Poluentes Químicos da Água/química , Impressão Molecular , Leite/química , Nanopartículas de Magnetita/química , Animais , beta-Ciclodextrinas/química , Limite de Detecção
16.
Int J Pharm ; 659: 124216, 2024 Jun 25.
Artigo em Inglês | MEDLINE | ID: mdl-38734272

RESUMO

The nasal administration route has been studied for the delivery of active molecules directed to the Central Nervous System, thanks to the anatomical connection between the nasal cavity and the brain. Dimethyl fumarate is used to treat relapsing-remitting multiple sclerosis, with a role as an immunomodulator towards T- T-cells and a cytoprotector towards neurons and glial cells. Its use in therapy is hindered by its low aqueous solubility, and low stability, due to hydrolysis and sublimation at room temperature. To overcome this limitation, in this study we evaluated the feasibility of using two amorphous ß-cyclodextrin derivatives, namely hydroxypropyl ß-cyclodextrin and methyl ß-cyclodextrin, to obtain a nasally administrable powder with a view to nose-to-brain administration. Initially, the interaction product was studied using different analytical methods (differential scanning calorimetry, Fourier transform infrared spectroscopy and powder X-ray diffraction) to detect the occurrence of binary product formation, while phase solubility analysis was used to probe the complexation in solution. The dimethyl fumarate-cyclodextrin binary product showing best solubility and stability properties was subsequently used in the development of a chitosan-based mucoadhesive nasally administrable powder comparing different preparative methods. The best performance in terms of both hydrolytic stability and DMF recovery was achieved by the powder obtained via freeze-drying.


Assuntos
Administração Intranasal , Quitosana , Fumarato de Dimetilo , Estabilidade de Medicamentos , Pós , Solubilidade , beta-Ciclodextrinas , Fumarato de Dimetilo/administração & dosagem , Fumarato de Dimetilo/química , Fumarato de Dimetilo/farmacocinética , Quitosana/química , Quitosana/administração & dosagem , beta-Ciclodextrinas/química , beta-Ciclodextrinas/administração & dosagem , Encéfalo/metabolismo , 2-Hidroxipropil-beta-Ciclodextrina/química , Espectroscopia de Infravermelho com Transformada de Fourier/métodos , Varredura Diferencial de Calorimetria , Difração de Raios X/métodos
17.
Biochim Biophys Acta Gen Subj ; 1868(8): 130643, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-38797254

RESUMO

Nanocarrier surface functionalization has been widely regarded as a promising approach for achieving precise and targeted drug delivery systems. In this work, the fabrication of functionalized-Ag-decorated Fe3O4@SiO2 (Fe3O4@SiO2-Ag) nanocarriers with folic acid (FA) and ß-cyclodextrin (BCD) exhibit a remarkable capacity for delivering two types of anticancer drugs, i.e., doxorubicin (DOX) and epirubicin (EPI), into cancer cells. The effective functionalization of Fe3O4@SiO2-Ag nanoparticles has been achieved through the use of cysteine (Cys) as an anchor for attaching FA and BCD via EDC-NHS coupling and Steglich esterification methods, respectively. The findings indicate that surface functionalization had no significant impact on the physicochemical characteristics of the nanoparticles. However, it notably affected DOX and EPI loading and release efficiency. The electrostatic conjugation of DOX/EPI onto the surface of Fe3O4@SiO2-Ag/Cys/FA and Fe3O4@SiO2-Ag/Cys/BCD exhibited maximum loading efficiency of 50-60% at concentration ratio of DOX/EPI to nanoparticles of 1:14. These nanocarriers also achieved an 40-47% DOX/EPI release over 36 days. Furthermore, the drug-loaded functionalized-nanocarrier showed cytotoxic effects on SK-MEL-2 cells, as demonstrated by an in vitro MTT assay. This suggests that the as-prepared functionalized-nanoparticles have promise as a carrier for the efficient anticancer drugs.


Assuntos
Antineoplásicos , Doxorrubicina , Portadores de Fármacos , Ácido Fólico , Dióxido de Silício , beta-Ciclodextrinas , Ácido Fólico/química , beta-Ciclodextrinas/química , Humanos , Doxorrubicina/farmacologia , Doxorrubicina/química , Doxorrubicina/administração & dosagem , Dióxido de Silício/química , Portadores de Fármacos/química , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/administração & dosagem , Epirubicina/farmacologia , Epirubicina/química , Sistemas de Liberação de Medicamentos , Liberação Controlada de Fármacos , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos
18.
Int J Biol Macromol ; 271(Pt 2): 132604, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38788866

RESUMO

A series of ternary polysaccharide hydrogels were facile prepared by incorporating carboxymethyl cellulose (CMC) into the carboxymethyl chitosan/carboxymethyl ß-cyclodextrin (CMCS/CMCD) complex solution based on multiple physical interactions. Structure properties of the CMC/CMCS/CMCD hydrogels were revealed by FTIR, XRD, SEM, and TG. The rheological and texture properties, temperature/pH-response behaviors, biocompatablity, and antimicrobial activity of the hydrogels were determined in detail. These results showed that the existence of electron force and hydrogen bond among three components leading to formation of the hydrogels, displaying good mechanical characteristic, stable solid-like rheological properties, controllable swelling and degradation behaviors, and excellent biocompatibility. Additionally, the swelling kinetics can be well described by the Schott's pseudo second order model. Moreover, the hydrogels loaded with cinnamic acid (CA) exhibited good antimicrobial activity against both Staphylococcus aureus and Escherichia coli, and the antimicrobial activity was related to the composition of the prepared hydrogels. The novel ternary polysaccharide hydrogels may have good application prospects in food and bio-medicine.


Assuntos
Carboximetilcelulose Sódica , Quitosana , Hidrogéis , Staphylococcus aureus , beta-Ciclodextrinas , Quitosana/química , Quitosana/análogos & derivados , Quitosana/farmacologia , Hidrogéis/química , beta-Ciclodextrinas/química , Carboximetilcelulose Sódica/química , Staphylococcus aureus/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Reologia , Antibacterianos/farmacologia , Antibacterianos/química , Polissacarídeos/química , Polissacarídeos/farmacologia , Temperatura , Concentração de Íons de Hidrogênio , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Testes de Sensibilidade Microbiana
19.
Food Chem ; 454: 139830, 2024 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-38820633

RESUMO

In this study, the ß-cyclodextrin encapsulated betanin (BET@ß-CD) with improved thermal stability and retention as well as the berberine (BBR) with aggregate induced luminescence effect were incorporated into corn amylose (CA) biomatrix to develop colorimetric/fluorescent dual-channel smart film. Results shown that the added functional components were uniformly distributed in the film matrix. The high tensile strength (78.87%), low water solubility (31.15%) and water vapor permeability (1.24 × 10-10 g Pa-1 s-1 m-1) of the film predicted its acceptable stability. It was worth mentioning that the film displayed excellent responsiveness to volatile ammonia (0.025-25 mg/mL) with at least 4 times recyclability. Application experiment demonstrated that the film can achieve macroscopic dynamic monitoring of the freshness of shrimps stored at 25 °C, 4 °C, -20 °C under daylight (red to yellow) and UV light (yellow-green to blue-green). Thus, the study suggests an attractive and effective strategy for constructing dual-mode smart packaging materials for food freshness detection.


Assuntos
Berberina , Betacianinas , Embalagem de Alimentos , Amido , beta-Ciclodextrinas , beta-Ciclodextrinas/química , Animais , Embalagem de Alimentos/instrumentação , Betacianinas/química , Berberina/química , Amido/química , Solubilidade
20.
Int J Pharm ; 659: 124264, 2024 Jun 25.
Artigo em Inglês | MEDLINE | ID: mdl-38788969

RESUMO

Nanotechnology-based diagnostic, and therapeutic approaches revolutionized the field of cancer detection, and treatment, offering tremendous potential for cost-effective interventions in the early stages of disease. This research synthesized bismuth oxide (Bi2O3) nanoparticles (NPs) that were modified with polycyclodextrin (PCD), and functionalized with glucose (Glu) to load curcumin (CUR) for CT imaging and chemo-radiotherapy applications in Breast Cancer. The prepared Bi2O3@PCD-CUR-Glu NPs underwent comprehensive characterization, encompassing various aspects, including cell migration, cytotoxicity, cellular uptake, blood compatibility, reactive oxygen species (ROS) generation ability, real-time PCR analysis, in-vivo safety assessment, in-vivo anti-tumor efficacy, as well as in-vitro CT contrast and X-ray RT enhancement evaluation. CT scan was conducted before and after (1 and 3 h) intravenous injection of Bi2O3@PCD-CUR-Glu NPs. Through the use of coupled plasma optical emission spectrometry (ICP-OES) analysis, the final prepared nanoparticle distribution in the Bab/c mice was assessed. The spherical NPs that were ultimately synthesized and had a diameter of around 80 nm demonstrated exceptional toxicity towards the SKBr-3 breast cancer cell line. The cell viability was at its lowest level after 48 h of exposure to a radiation dose of 2 Gy at a concentration of 100 µg/mL. The combined treatment involving using Bi2O3@PCD-CUR-Glu NPs along with X-ray radiation showed a substantial increase in the generation of ROS, specifically a remarkable 420 % growth. Gene expression analysis indicated that the expression levels of P53, and BAX pro-apoptotic genes were significantly increased. The in-vitro CT imaging analysis conducted unequivocally demonstrated the notable superiority of NPs over Omnipaque in terms of X-ray absorption capacity, a staggering 1.52-fold increase at 80 kVp. The resultsdemonstrated that the targeted Bi2O3@PCD-CUR-Glu NPs could enhance the visibility of a small mice tumor that is detectable by computed tomography and made visible through X-ray attenuation. Results suggested that Bi2O3@PCD-CUR-Glu NPs, integrated with CT imaging and chemo-radiotherapy, have great potential as a versatile theranostic system for clinical application.


Assuntos
Bismuto , Neoplasias da Mama , Curcumina , Camundongos Endogâmicos BALB C , Nanopartículas , Tomografia Computadorizada por Raios X , beta-Ciclodextrinas , Curcumina/administração & dosagem , Curcumina/química , Curcumina/farmacologia , Animais , Neoplasias da Mama/tratamento farmacológico , Neoplasias da Mama/patologia , Neoplasias da Mama/terapia , Feminino , Humanos , Linhagem Celular Tumoral , Tomografia Computadorizada por Raios X/métodos , beta-Ciclodextrinas/química , Bismuto/química , Bismuto/administração & dosagem , Nanopartículas/química , Camundongos , Espécies Reativas de Oxigênio/metabolismo , Quimiorradioterapia/métodos , Sobrevivência Celular/efeitos dos fármacos , Antineoplásicos/administração & dosagem , Antineoplásicos/farmacologia , Antineoplásicos/química
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