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1.
RSC Adv ; 14(15): 10199-10208, 2024 Mar 26.
Artículo en Inglés | MEDLINE | ID: mdl-38544942

RESUMEN

This article describes the synthesis, characterization (1H NMR, 13C NMR, FT-IR, HRMS and XRD), UV-Vis absorption and fluorescence spectra, theoretical analysis, evaluation of nonlinear optical properties (NLO), thermal analysis and determination of the hemolytic capacity of the compound (E)-N-(4-(3-(benzo[d][1,3]dioxol-5-yl)acryloyl)phenyl)quinoline-3-carboxamide (5). Radiological findings showed that compound 5 crystallized in space group Pca21. Furthermore, theoretical DFT studies performed with the B3LYP and M062X functionals showed good agreement with the experimental results and provided valuable information on the molecular and electronic structure, reactivity, polarizability, and kinematic stability of the compound. Besides, compound 5 did not show any hemolytic effect on human erythrocytes and exhibited strong NLO properties. The TG and DTA thermograms of quinoline-chalcone (5) revealed a multi-step thermal decomposition process with a total mass loss of 83.2%, including water content loss. The DTA curves exhibited endothermic peaks corresponding to decomposition steps, melting point, and thermochemical transition. Additionally, exothermic peaks in the DTA thermograms align with significant mass loss, confirming the compound's melting point and water content, as validated by X-ray diffraction analysis. These results contribute to the advancement of research on compounds with NLO properties and offer a promising avenue for the development of substances potentially applicable to optical devices in the biomedical field.

2.
Plants (Basel) ; 12(4)2023 Feb 12.
Artículo en Inglés | MEDLINE | ID: mdl-36840166

RESUMEN

This research aimed to identify the phenolic profile and composition of the aerial parts of three native species used in traditional medicine in the Andean Altiplano of northern Chile: Clinopodium gilliesii (Benth.) Kuntze [Lamiaceae] (commonly known as Muña-Muña), Mutisia acuminata Ruiz & Pav. var. hirsuta (Meyen) Cabrera [Asteraceae] (commonly known as Chinchircoma), and Tagetes multiflora (Kunth), [Asteraceae] (commonly known as Gracilis), as well as to evaluate their potential inhibitory effects against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Polyphenolic enriched-extracts (PEEs) of the species were prepared and analyzed and the main components were quantified using HPLC-DAD. In total, 30 phenolic compounds were identified and quantified in all species, including simple phenolics, hydroxycinnamic acids, flavan-3-ols (monomers and polymers), flavanones, and flavonols. In addition, other main phenolics from the extracts were tentatively identified by ESI-MS-MS high-resolution analysis. T. multiflora extract showed the greatest anti-AChE and BChE activity in comparison with C. gilliesii and M. acuminata extracts, being the anti-AChE and BChE activity weak in all extracts in comparison to galantamine control. To comprise to better understand the interactions between cholinesterase enzymes and the main phenolics identified in T. multiflora, molecular docking analysis was conducted.

3.
Front Pharmacol ; 13: 1003264, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-36160442

RESUMEN

Background: There is abundant ethnopharmacological evidence the uses of regarding Solanum species as antitumor and anticancer agents. Glycoalkaloids are among the molecules with antiproliferative activity reported in these species. Purpose: To evaluate the anticancer effect of the Solanum glycoalkaloid tomatine in hepatocellular carcinoma (HCC) in vitro (HepG2 cells) and in vivo models. Methods: The resazurin reduction assay was performed to detect the effect of tomatine on cell viability in human HepG2 cell lines. Programmed cell death was investigated by means of cellular apoptosis assays using Annexin V. The expression of cancer related proteins was detected by Western blotting (WB). Reactive oxygen species (ROS) and calcium were determined by 2,7-dichlorodihydrofluorescein diacetate and Fluo-4, respectively. Intrahepatic HepG2 xenograft mouse model was used to elucidate the effect of tomatine on tumor growth in vivo. Results and Discussion: Tomatine reduced HepG2 cell viability and induced the early apoptosis phase of cell death, consistently with caspase-3, -7, Bcl-2 family, and P53 proteins activation. Furthermore, tomatine increased intracellular ROS and cytosolic Ca+2 levels. Moreover, the NSG mouse xenograft model showed that treating mice with tomatine inhibited HepG2 tumor growth. Conclusion: Tomatine inhibits in vitro and in vivo HCC tumorigenesis in part via modulation of p53, Ca+2, and ROS signalling. Thus, the results suggest the potential cancer therapeutic use of tomatine in HCC patients.

4.
Antioxidants (Basel) ; 11(6)2022 Jun 01.
Artículo en Inglés | MEDLINE | ID: mdl-35740001

RESUMEN

In this work, we report the synthesis of curcuminoids with ionic liquid characteristics, obtained by incorporating alkyl-substituted pyridinium moiety rather than one phenyl group through a two-step process. The antioxidant capacity of the obtained compounds was evaluated in vitro by 1,1-diphenyl-picrylhydrazyl (DPPH) free radical scavenging and ferric reducing antioxidant power (FRAP) assays, showing that some derivatives are more potent than curcumin. Pyridine curcuminoids (group 4) and curcuminoid N-alkylpyridinium salts with two methoxyl groups in the phenyl ring (group 7), presented the best antioxidant capacity. The experimental results were rationalized by density functional theory (DFT) calculations of the bond dissociation enthalpy (BDE) for O-H in each compound. The computational calculations allowed for insight into the structural-antioxidant properties relationship in these series of compounds. BDEs, obtained in the gas phase and water, showed a notable impact of water solvation on the stabilization of some radicals. The lower values of BDEs in the water solution correspond to the structurally related compounds curcuminoid-pyridine 4c and curcuminoid pyridinium salt 7a, which is consistent with the experimental results. Additionally, an assessment of cell viability and cell migration assays was performed for human colon cancer (HT29), human breast cancer (MCF7) cells, in addition to NIH3T3 murine fibroblast, as a model of non-cancer cell type. These compounds mainly cause inhibition of the cell migration observed in MCF7 cancer cells without affecting the non-tumoral NIH3T3 cell line: Neither in viability nor in migration.

5.
Bioorg Chem ; 126: 105914, 2022 09.
Artículo en Inglés | MEDLINE | ID: mdl-35649316

RESUMEN

The skin and soft tissue infections (SSTIs) -producing pathogens have acquired resistance to a wide range of antimicrobials, thus it is highly relevant to have new treatment alternatives. In this study, we report the synthesis, characterization, and antibacterial activity of three novel series of ionic liquids (ILs) derived from benzoic and hydroxybenzoic acids, with different lengths of the alkyl chain. The minimum inhibitory concentration (MIC) were tested in Gram-positive: Pseudomonas aeruginosa, Staphylococcus aureus, Staphylococcus epidermidis, and Streptococcus pyogenes, and Gram-negative: Acinetobacter baumannii and Escherichia coli, showing a MIC range of 0.01562-2.0 mM, with the activity varying according to the aromatic ring functionalization and the length of the alkyl chains. Regarding the antibiofilm activity, different efficacy was observed among the different ILs, some of them presenting antibiofilm activities close to 80% as in the case of those derived from syringic acid with an alkyl chain of six carbon atoms against Pseudomonas aeruginosa. Furthermore, the cell viability in HaCaT cells was determined, showing a half maximal effective concentration (EC50) values higher than the MIC values. The antimicrobial and antibiofilm results, along with not producing cellular toxicity at the MIC values shows that these ILs could be a promising alternative against SSTIs.


Asunto(s)
Antiinfecciosos , Líquidos Iónicos , Infecciones de los Tejidos Blandos , Antibacterianos/farmacología , Antiinfecciosos/farmacología , Bacterias , Biopelículas , Escherichia coli , Humanos , Hidroxibenzoatos/farmacología , Líquidos Iónicos/farmacología , Pruebas de Sensibilidad Microbiana , Pseudomonas aeruginosa
6.
Materials (Basel) ; 14(19)2021 Sep 26.
Artículo en Inglés | MEDLINE | ID: mdl-34639987

RESUMEN

A prospective study of the dye properties of non-toxic lawsone thiophenyl derivatives, obtained using a green synthetic methodology allowed for the description of their bathochromic shifts in comparison to those of lawsone, a well-known natural pigment used as a colorant that recently also has aroused interest in dye-sensitized solar cells (DSSCs). These compounds exhibited colors close to red, with absorption bands in visible and UV wavelength range. The colorimetric study showed that these compounds exhibited a darker color than that of lawsone within a range of colors depending on the substituent in the phenyl ring. Computational calculations employing Density Functional Theory (DFT) and Time-Dependent Density Functional Theory (TD-DFT), showed that the derivatives have lower excitation energies than lawsone, while the alignment of their frontier orbitals regarding the conduction bands of TiO2 and ZnO and the redox potential of the electrolyte I-/I3- suggests that they could be employed as sensitizers. The study of the interactions of the lawsone and a derivative with a TiO2 surface model by different anchoring modes, showed that the adsorption is thermodynamically favored. Natural bond orbital (NBO) analysis indicates a two-center bonding (BD) O-Ti as the main interaction of the dyes with TiO2.

7.
Int J Food Sci ; 2021: 7105170, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-34568484

RESUMEN

With the continuous increase in research on lipids, technologies and the development of chemical-analytical methods associated with the characterization and monitoring of different processes that involve modifications in edible fats are increasing. The beneficial effect of lipids, especially those essential for the health of the population, is widely known. However, degradation compounds are also produced that eventually have negative effects. In this dual context, the monitoring of the changes suffered by nutritional compounds can be obtained thanks to the development of technologies and analytical methods applied to the study of lipids. The modifications that lipids undergo can be followed by a wide variety of methods, ranging from the basic ones associated with simple chemical titrations to the more complex ones associated with sophisticated laboratory equipment. These determinations involve chemical and/or physical quantification of lipids to know an initial condition on the major and minor components. In addition to technologies that allow monitoring during more complex processes such as thermal deterioration, in multiple conditions depending on the objective of the study, this review could benefit a comprehensive understanding of lipid deterioration for future developments and research in the study of fats and oils for human consumption.

8.
Bioorg Chem ; 115: 105289, 2021 10.
Artículo en Inglés | MEDLINE | ID: mdl-34426154

RESUMEN

Bacterial infections are nowadays among the major threats to public health worldwide. Thus, there is an urgent and increased need for new antimicrobial agents. As a result, the exploration of the antimicrobial properties of different substances including ionic liquids (ILs) has recently attracted great attention. The present work is aimed at evaluating how the addition of halogens and hydrophobic substituents on alkylimidazolium units of ILs as well as the increase in their chain lengths affects the antimicrobial properties of such ILs. After their synthesis, the antibacterial activities of these compounds against Pseudomona aeruginosa, Escherichia coli, and Staphylococcus aureus are determined by measuring their minimal inhibitory concentrations (MICs). Key features in ILs-membrane interactions are also studied using long-term all-atom molecular dynamics simulations (MDs). The results show that these ILs have good antibacterial activity against S. aureus, E. coli, and P. aeruginosa, with MIC values range from <7.81 to 62.50 µM. The antimicrobial property of tert-butyl N-methylphenolimidazolium salts (denoted as 8b and 8c) is particularly better with MIC values of < 7.81 µM. The antibacterial efficacy is also found to depend on the alkyl chain length and substituents on the phenolic ring. Finally, MDs done for ILs in a phosphatidylcholine (POPC) bilayer show key features in the mechanism of IL-induced membrane disruption, where the ILs are inserted as clusters into one side of the bilayer until saturation is reached. This insertion increases "leaflet strain" up to critical threshold, likely triggering the morphological disruption of the membranes in the microbes.


Asunto(s)
Antibacterianos/farmacología , Imidazoles/farmacología , Líquidos Iónicos/farmacología , Fenoles/farmacología , Antibacterianos/síntesis química , Antibacterianos/química , Cationes/química , Cationes/farmacología , Relación Dosis-Respuesta a Droga , Escherichia coli/efectos de los fármacos , Imidazoles/química , Líquidos Iónicos/síntesis química , Líquidos Iónicos/química , Pruebas de Sensibilidad Microbiana , Simulación de Dinámica Molecular , Estructura Molecular , Fenoles/química , Pseudomonas aeruginosa/efectos de los fármacos , Staphylococcus aureus/efectos de los fármacos , Relación Estructura-Actividad
9.
Polymers (Basel) ; 13(13)2021 Jun 24.
Artículo en Inglés | MEDLINE | ID: mdl-34202791

RESUMEN

The aim of this work was to characterize and optimize the formation of molecular complexes produced by the association of calcium alginate and reduced glutathione (GSH). The influence of varying concentrations of calcium and GSH on the production of microcapsules was analyzed using response surface methodology (RSM). The microcapsules were characterized by thermogravimetric analysis (TGA-DTG) and infrared spectroscopy (FTIR) in order to assess the hydration of the complexes, their thermal stability, and the presence of GSH within the complexes. The optimum conditions proposed by RSM to reach the maximum concentration of GSH within complexes were a 15% w/v of GSH and 1.25% w/v of CaCl2, with which a theorical concentration of 0.043 mg GSH per mg of CAG complex was reached.

10.
Antioxidants (Basel) ; 10(5)2021 Apr 24.
Artículo en Inglés | MEDLINE | ID: mdl-33923315

RESUMEN

Avocado oil is considered a highly prized food due to its nutritional contribution. On the other hand, Aristotelia chilensis (Molina) Stuntz (Elaeocarpaceae), common name "maqui", is an endemic fruit in Chile, well known for its exceptional antioxidant properties. In general, maqui by-products such as leaves are considered as waste. Thus, maqui leaves extracts were used to improve the stability of vegetable oils, particularly avocado oil. Hence, avocado oil was fortified with two extracts (ethyl ether and methanol) obtained of maqui leaves and exposed to 120 °C for 386 h in an oven. The results showed a high content of monounsaturated fatty acids (69.46%, mainly oleic acid), followed by polyunsaturated fatty acids (16.41%, mainly linoleic acid) and finally saturated fatty acids (14.13%). The concentration of the total phenolic compounds in the pure oil, ethyl ether and methanol maqui leaves extracts were 45.8, 83.7, and 4100.9 ppm, respectively. In addition, the antioxidant activity was 5091.6 and 19,452.5 µmol Trolox eq/g for the ethyl ether and methanol extracts, respectively. The secondary degradation compounds showed significant differences between the fortified and non-fortified samples after 144 h and the TG/DTG analysis showed a significant increment of 7 °C in the degradation temperature (Tonset) of avocado oil fortified with the methanol extract when compared to the non-fortified oil and fortified oil with ethyl ether extract. After heating for 336 h, fortified oil with methanol extract reached the limit percentages of polar compounds, while pure oil reached it in a shorter time, i.e., 240 h. Based on the results, avocado oil can be protected with natural additives such as extracts obtained from maqui leaves, leading to an increase in its thermo-oxidative stability.

11.
Data Brief ; 31: 105902, 2020 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-32637503

RESUMEN

The data article refers to the paper "supramolecular hydrogel based on cellulose for sustained release of therapeutic substances with antimicrobial and wound healing properties"[1]. The dataset includes the synthesis and characterization of (E)-1,3-bis(4-(allyloxy)phenyl)prop­2-en-1-one (3) (crosslinking agent). Moreover, the multiwall carbon nanotubes (MWCNTs) synthesis and functionalization (MWCNTs-COOH) are described. The formulation obtained by adding multiwalled carbon nanotubes-COOH with the crosslinked cellulose-chalcone hydrogel is abbreviated as MWCNTsCCH, and the same formulation loaded with therapeutic substances (TS) is named MWCNTsCCH-TS. The MWCNTsCCH database such as components and their amounts, swelling degree, thermogravimetric analysis, and cytotoxicity evaluation are depicted. Finally, to elucidate the mechanism of therapeutic substances release, the obtained averages of the release profiles were fitted through mathematical models.

12.
Carbohydr Polym ; 242: 116383, 2020 Aug 15.
Artículo en Inglés | MEDLINE | ID: mdl-32564841

RESUMEN

A multifaceted hydrogel-based formulation was reported. The hydrogel was prepared by crosslinking cellulose and substituted chalcone. Moreover, the formulation was conjugated with carbon nanotubes with the aim of increasing the loading amount of bioactive compounds such as allantoin, dexpanthenol, resveratrol and linezolid. The hydrogel formation was confirmed by swelling tests, FT-IR spectroscopy, thermogravimetric analysis and SEM. The hydrogel showed an improved release rate of therapeutic substances, exhibiting a simultaneous and coordinated release according to the chromatographic studies. The efficacy of drug release was confirmed by wound closure and in vivo wound healing studies that showed promising healing results. The antibacterial assays demonstrated that the sustained release of linezolid tends to be very effective. In conclusion, a multifaceted formulation based on carbon nanotube-containing cellulose-chalcone was developed that can potentially be utilized in treating complex wounds owing to its improved wound healing properties and prevention of potential infections.


Asunto(s)
Antibacterianos/farmacología , Celulosa/farmacología , Enterococcus faecium/efectos de los fármacos , Hidrogeles/farmacología , Cicatrización de Heridas/efectos de los fármacos , Animales , Antibacterianos/química , Línea Celular , Celulosa/química , Liberación de Fármacos , Hidrogeles/química , Cinética , Sustancias Macromoleculares/química , Sustancias Macromoleculares/farmacología , Ratones , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Tamaño de la Partícula , Ratas , Ratas Sprague-Dawley , Espectroscopía Infrarroja por Transformada de Fourier , Propiedades de Superficie , Temperatura
13.
An Acad Bras Cienc ; 92(2): e20190615, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-32556053

RESUMEN

Hedychium coronarium J. Koening, belonging to Zingiberaceae family, is a perennial herb with fleshly aromatic rhizomes. There are no information about the antiplatelet properties of essential oils (EOs) from rhizomes (HCR) and leaves (HCL) of this herb, additionally, there are reports about the antibacterial activity of the Zingiberaceae species, however, no studies have been carried out in the Colombian Amazon Region. The EOs were characterized by GC-MS, the antiaggregant activity was assessed by ADP and Collagen as platelet agonist and the antibacterial activity against E. faecalis and S. aureus were evidenced by the determination of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). A high content of oxygenated monoterpenes were found in HCL essential oil (EO) and 20 compounds were identified in HCR EO. The HCL EO showed antiaggregant activity when collagen was used and HCR EO showed a concentration-dependent activity against ADP and collagen, meanwhile only the HCR EO showed antibacterial activity against E. faecalis and S. aureus.


Asunto(s)
Antibacterianos/farmacología , Enterococcus faecalis/efectos de los fármacos , Aceites Volátiles/farmacología , Inhibidores de Agregación Plaquetaria/farmacología , Rizoma/química , Staphylococcus aureus/efectos de los fármacos , Zingiberaceae/química , Antibacterianos/aislamiento & purificación , Cromatografía de Gases y Espectrometría de Masas , Pruebas de Sensibilidad Microbiana , Hojas de la Planta/química , Inhibidores de Agregación Plaquetaria/aislamiento & purificación , Rizoma/clasificación , Zingiberaceae/clasificación
14.
Molecules ; 24(19)2019 Sep 26.
Artículo en Inglés | MEDLINE | ID: mdl-31561437

RESUMEN

The bacterial resistance to antibiotics has compromised the therapies used for bacterial infections. Nowadays, many strategies are being carried out to address this problem. Among them, the use of natural compounds like cinnamic and p-coumaric acids stands out. Nevertheless, their utilization is limited because of their unfavorable physicochemical properties. Due to the lack of new therapeutic alternatives for bacterial infections, novel strategies have emerged, such as the use of ionic liquids; given that they can show a broad spectrum of antibacterial activity, this is why we herein report the antibacterial and antibiofilm activity of a series of N-alkylimidazolium salts functionalized with p-coumaric and cinnamic acids. The results from this study showed better antibacterial activity against Gram-positive bacteria, with a predominance of the salts derived from coumaric acid and a correlation with the chain length. Additionally, a lower efficacy was observed in the inhibition of biofilm formation, highlighting the antibiofilm activity against Staphylococcus aureus, which decreased the production of the biofilm by 52% over the control. In conclusion, we suggest that the salts derived from p-coumaric acid are good alternatives as antibacterial compounds. Meanwhile, the salt derived from cinnamic acid could be a good alternative as an antibiofilm compound.


Asunto(s)
Antiinfecciosos/química , Antiinfecciosos/farmacología , Biopelículas/efectos de los fármacos , Cinamatos/química , Imidazoles/química , Imidazoles/farmacología , Propionatos/química , Ácidos Cumáricos , Líquidos Iónicos , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Simulación de Dinámica Molecular , Relación Estructura-Actividad
15.
Molecules ; 23(9)2018 Sep 14.
Artículo en Inglés | MEDLINE | ID: mdl-30223457

RESUMEN

Keeping in mind the concept of green chemistry, this research aims to synthesize and characterize new ionic liquids (ILs) derived from N-cinnamyl imidazole with different sizes of alkyl chains (1, 6, 8, and 10 carbon atoms), and evaluate their antibacterial activity against Skin and soft tissue infections (SSTIs) causative bacteria. The antibacterial screening was carried out by agar well diffusion and the Minimum Inhibitory Concentration (MIC) and Half Maximum Inhibitory Concentration (IC50) of the different ILs were determined by microdilution in broth, also Molecular dynamics simulations were performed to study the interaction mechanism between ILs and membranes. The MIC value in Gram-positive bacteria showed that as the hydrocarbon chain increases, the MIC value decreases with a dose-dependent effect. Furthermore, Gram-negative bacteria showed high MIC values, which were also evidenced in the antibacterial screening. The molecular dynamics showed an incorporation of the ILs with the longer chain (10 C), corresponding to a passive diffusion towards the membrane surface, for its part, the ILs with the shorter chain due to its lack of hydrophobicity was not incorporated into the bilayer. Finally, the new ILs synthesized could be an alternative for the treatment of Gram-positive bacteria causative of SSTIs.


Asunto(s)
Antibacterianos/química , Antibacterianos/síntesis química , Imidazoles/síntesis química , Líquidos Iónicos/síntesis química , Animales , Antibacterianos/farmacología , Relación Dosis-Respuesta a Droga , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Tecnología Química Verde , Humanos , Imidazoles/química , Imidazoles/farmacología , Líquidos Iónicos/química , Líquidos Iónicos/farmacología , Pruebas de Sensibilidad Microbiana , Simulación de Dinámica Molecular , Infecciones de los Tejidos Blandos/tratamiento farmacológico , Infecciones Cutáneas Estafilocócicas/tratamiento farmacológico
16.
Artículo en Inglés | MEDLINE | ID: mdl-30151018

RESUMEN

The oxidative stress is characterized by an imbalance between the oxidizing agents and antioxidants; meanwhile, the consumption of antioxidants has been considered as an important tool in the prevention of oxidative stress and its consequences. Pitavia punctata (R. & P.) Molina is an endemic arboreal species from the Chilean Coast Range, in which a large amount of flavonoids has been described. This work focused on characterizing and evaluating, in human erythrocytes, the antioxidant capacity and membrane protection of P. punctata extracts and the in vitro protection of the oxidation of the Low Density Lipoprotein (LDL). The phytochemical screening revealed the presence of Quercetin derivatives and flavonoids, such as (-)-Epicatechin, Kaempferol, and derivatives. The methanolic extract presented an important antioxidant activity, protecting the membrane integrity of the red blood cells against the oxidative damage caused by Hypochlorous acid and inhibiting the oxidation of the LDL lipoprotein.

17.
An Acad Bras Cienc ; 90(2 suppl 1): 2331-2346, 2018 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-30066746

RESUMEN

Currently, cancer is the second most common cause of death in the United States, exceeded only by heart disease. Chemotherapy traditionally suffers from a non-specific distribution, with only a small fraction of the drug reaching the tumor, in this sense, the use of dendrimers incorporating drugs non-covalently encapsulated inside the dendrimer or covalently conjugated have proven to be effectives against different cancer cell lines. However, at present the dendrimers used as drug-carriers still do not meet the necessary characteristic to be considered as an ideal dendrimer for drug delivery; high toxicity, bio-degradability, low toxicity, biodistribution characteristics, and favorable retention with appropriate specificity and bioavailability have not been fully covered by the current available dendrimers. However, the development and study of new dendrimers drug-carriers continues to be an important tool in the cancer therapy as they can be functionalized with varied ligands to reach the tumor tissue through the different body barriers in the body with minimal loss of activity in the bloodstream, have the ability to selectively kill tumor cells without affecting the normal cells and most important with a release mechanism controlling actively. Given the continuous efforts and research in this area of interest, we presented in this review the work done with a special emphasis on the development of dendrimers as a major tool in the combination with drugs, as a potential adjunctive agent in anticancer therapy.


Asunto(s)
Antineoplásicos/administración & dosificación , Dendrímeros/administración & dosificación , Portadores de Fármacos/administración & dosificación , Nanopartículas/administración & dosificación , Neoplasias/tratamiento farmacológico , Animales , Humanos
18.
Comb Chem High Throughput Screen ; 20(8): 696-702, 2017.
Artículo en Inglés | MEDLINE | ID: mdl-28571539

RESUMEN

AIM AND OBJECTIVE: According to our interest in developing new methods for the construction of intricate molecules, a reliable polymer-supported (-)-8-phenylmenthyl chiral auxiliary for the addition of different nucleophiles to chiral-supported N-acyliminium precursors were developed. MATERIALS AND METHODS: Merrifield resin was employed to anchor (-)-8-phenylmenthol, which was prepared by nitration of (-)-8-phenylmenthyl chloroacetate followed by reduction of nitro group and subsequent Merrifield resin coupling. Treatment of a suspension of polymer-supported chloroformate and piperidinone in the presence of Et3N resulted in attachment of the substrate onto the solid-support. Treatment of the resulting resin with LiEt3BH/MeOH afforded methoxypiperidine in 87% yield. Then, the addition of allyltrimethylsilane, TMSCN, 2-(trimethylsiloxy)propene and triisopropylsilyloxyfuran and others to the N-acyliminium ion derived from chiral 2- methoxypiperidine carbamate was studied. RESULTS: The stereochemical outcome of the addition of nucleophiles to the supported N-acyliminium ion derived from 2-methoxypiperidine carbamate was proposed through the Si-face, affording after resin cleavage 2-substituted piperidines in 70%-84% yields and selectivities ranging from 4:1-11.1. Moreover, the key intermediates of chiral piperidines have been employed for the synthesis of simple chiral alkaloids such as (R)-pipecolic acid, (R)-pelletierine, (S)-coniine and (R,R)-myrtine. CONCLUSION: The proposed supported-chiral auxiliary for asymmetric approach may be expected to result not only in efficient solid-phase syntheses of a wide range of alkaloids but also in the development of useful new solid-phase methodologies, particularly for the asymmetric additions to iminium precursors. This work describes the first example of solid-phase synthesis by using supported (-)-8-phenylmenthyl as an effective chiral inductor and would be useful for the synthesis of chiral building block libraries.


Asunto(s)
Ciclohexanos/química , Iminas/química , Mentol/análogos & derivados , Piperidinas/síntesis química , Polímeros/química , Técnicas de Síntesis en Fase Sólida , Iones/química , Mentol/química , Estructura Molecular , Piperidinas/química , Estereoisomerismo
19.
Food Chem ; 213: 554-560, 2016 Dec 15.
Artículo en Inglés | MEDLINE | ID: mdl-27451217

RESUMEN

The phenolic compounds of wine contribute to color and astringency, also are responsible for the oxidation state and bitterness. Due the importance of these molecules, different techniques have been used to modulate their concentration such as natural or synthetic polymeric agents. Among the polymeric agents, PVPP is one of the most used, but lacks of selectivity and has a limited pH range. Therefore, the aim of this study was the synthesis of a new polymer, poly(N-(3-(N-isobutyrylisobutyramido)-3-oxopropyl)acrylamide) (P-NIOA), for removal of phenolic compounds, as a potential agent for the fining of wine. The new polymer affinity was studied using HPLC-DAD for different polyphenols using PVPP as a control. The results showed that the new polymer has a similar removal as PVPP, but with lower affinity to resveratrol. The interactions established between polymers and polyphenols were studied using computational chemistry methods demonstrating a direct correlation with the experimental affinity data.


Asunto(s)
Resinas Acrílicas/química , Fraccionamiento Químico/métodos , Polifenoles/química , Vino
20.
Platelets ; 26(8): 764-70, 2015.
Artículo en Inglés | MEDLINE | ID: mdl-25548968

RESUMEN

The purpose of this research was to investigate the mechanisms of antiplatelet action of Cyperus digitatus. The antiplatelet action of C. digitatus was studied on platelet function: secretion, adhesion, aggregation, and sCD40L release. The platelet ATP secretion and aggregation were significantly inhibited by CDA (ethyl acetate extract) at 0.1 mg/ml and after the incubation of whole blood with CDA, the platelet coverage was inhibited by 96 ± 3% (p < 0.001). At the same concentration, CDA significantly decreased sCD40L levels. The mechanism of antiplatelet action of CDA could be by NF-κB inhibition and that is cAMP independent. In conclusion, C. digitatus extract may serve as a new source of antiplatelet agents for food and nutraceutical applications.


Asunto(s)
Plaquetas/efectos de los fármacos , Plaquetas/metabolismo , Cyperus/química , Extractos Vegetales/farmacología , Inhibidores de Agregación Plaquetaria/farmacología , Adenosina Trifosfato/metabolismo , Ligando de CD40/metabolismo , AMP Cíclico/metabolismo , Humanos , Agregación Plaquetaria/efectos de los fármacos , Pruebas de Función Plaquetaria
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