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1.
J Mater Chem B ; 9(37): 7698-7712, 2021 09 29.
Article in English | MEDLINE | ID: mdl-34586143

ABSTRACT

Fluorescent bioimaging is an excellent tool in cellular biology, and it will be a powerful technique in modern medicine as a noninvasive imaging technology where tumoral and normal cells must be distinguished. One of the differences between normal and cancer cells is the intracellular pH. Therefore, the design and synthesis of pH-responsive fluorescent materials are required. Organotin Schiff bases showed halofluorochromic behavior in solution. Microwave-assisted synthesis showed better reaction times and chemical yields compared with conventional heating. All compounds were fully characterized by spectroscopic and spectrometric techniques. The halofluorochromism study showed that some molecules in acidic media have the maximum luminescence intensity due to protonation. All the fluorescent tin complexes showed cell staining on hepatocyte and MCF-7 cells by confocal microscopy. The theoretical study has enabled us to rationalize the optical properties and the halofluorochromism for compounds 1 and 2 synthesized in this work. Our results showed that the emission decrease, in the acid and basic media for compounds 1 and 2, respectively, is caused by intramolecular charge transfer (ICT) deactivation.


Subject(s)
Fluorescent Dyes/chemistry , Organotin Compounds/chemistry , Schiff Bases/chemistry , Cell Survival/drug effects , Density Functional Theory , Hepatocytes/cytology , Hepatocytes/pathology , Humans , Hydrogen-Ion Concentration , MCF-7 Cells , Microscopy, Confocal , Molecular Conformation , Organotin Compounds/pharmacology , Spectrometry, Fluorescence
2.
Vector Borne Zoonotic Dis ; 18(10): 548-553, 2018 10.
Article in English | MEDLINE | ID: mdl-29969388

ABSTRACT

An organic salt and four metal complexes derived from azole were evaluated against embryonated Toxocara canis eggs (TCE). The new organic salt, (LH)+(FeCl4)-, where L = 3,5-bis(3,5-dimethylpyrazole-1-ylmethyl)toluene (5), a potential environmental disinfectant, was isolated as an air-stable yellow solid and characterized by elemental analysis, electrical conductivity, mass spectrometry, and infrared and ultraviolet/visible spectroscopy. In addition, the structure of 5 was determined by single-crystal X-ray diffraction. Compound 2 showed high anti-TCE activity. Interestingly, these compounds showed little effect on hepatocytes, indicating that they are not cytotoxic. These results will assist in the design of anti-TCE compounds.


Subject(s)
Anthelmintics/pharmacology , Azoles/pharmacology , Coordination Complexes/pharmacology , Ovum/drug effects , Toxocara canis/drug effects , Animals , Anthelmintics/chemical synthesis , Anthelmintics/chemistry , Azoles/chemical synthesis , Azoles/chemistry , Coordination Complexes/chemical synthesis , Coordination Complexes/chemistry , Models, Molecular , Molecular Structure
3.
J Org Chem ; 82(5): 2375-2385, 2017 03 03.
Article in English | MEDLINE | ID: mdl-28135091

ABSTRACT

We report the design, synthesis, and characterization of two new fluorescent molecular rotors of boron derived from Schiff bases: (2,4,8,10-tetra-tert-butyl-6-phenyldibenzo[d,h][1,3,6,2]dioxazaboronine (3) and 1,4-bis(2,4,8,10-tetra-tert-butyldibenzo[d,h][1,3,6,2]dioxazaboronin-6-yl)benzene (4), as well as the free ligand 2-[[(3,5-di-tert-butyl-2-hydroxyphenyl)imino]methyl]-4,6-di-tert-butylphenol 1. All compounds were fully characterized by NMR (1H, 11B, and 13C), IR, UV/vis, fluorescence spectroscopy, and high-resolution mass spectrometry. The crystal structures of 3 and 4 showed tetracoordinated boron atoms with semiplanar skeleton ligands. The free rotation of the fluorescent molecular rotor, only observed in the binuclear compound, was decreased with increasing viscosity, while the quantum yield was increased. Interestingly, the property of reversible thermochromism was found in organoboron 4 in the solid state. DFT calculations to determine the both complexes have free rotation around the CPh-B1 bond. The boron compounds 3 and 4 have shown low cytotoxicity activity in cell line A-431 and low green staining in cells.


Subject(s)
Boron Compounds/chemistry , Fluorescent Dyes/chemistry , Schiff Bases/chemistry , Spectrum Analysis/methods
4.
Int J Nanomedicine ; 11: 4787-4798, 2016.
Article in English | MEDLINE | ID: mdl-27703347

ABSTRACT

Coriander leaves and seeds have been highly appreciated since ancient times, not only due to their pleasant flavors but also due to their inhibitory activity on food degradation and their beneficial properties for health, both ascribed to their strong antioxidant activity. Recently, it has been shown that coriander leaf extracts can mediate the synthesis of metallic nanoparticles through oxidation/reduction reactions. In the present study, extracts of coriander leaves and seeds have been used as reaction media for the wet chemical synthesis of ultrafine silver nanoparticles and nanoparticle clusters, with urchin- and tree-like shapes, coated by biomolecules (mainly, proteins and polyphenols). In this greener route of nanostructure preparation, the active biocompounds of coriander simultaneously play the roles of reducing and stabilizing agents. The morphological and microstructural studies of the resulting biosynthesized silver nanostructures revealed that the nanostructures prepared with a small concentration of the precursor Ag salt (AgNO3 =5 mM) exhibit an ultrafine size and a narrow size distribution, whereas particles synthesized with high concentrations of the precursor Ag salt (AgNO3 =0.5 M) are polydisperse and formation of supramolecular structures occurs. Fourier transform infrared and Raman spectroscopy studies indicated that the bioreduction of the Ag- ions takes place through their interactions with free amines, carboxylate ions, and hydroxyl groups. As a consequence of such interactions, residues of proteins and polyphenols cap the biosynthesized Ag nanoparticles providing them a hybrid core/shell structure. In addition, these biosynthesized Ag nanomaterials exhibited size-dependent plasmon extinction bands and enhanced bactericidal activities against both Gram-positive and Gram-negative bacteria, displaying minimal inhibitory Ag concentrations lower than typical values reported in the literature for Ag nanoparticles, probably due to the synergy of the bactericidal activities of the Ag nanoparticle cores and their capping ligands.


Subject(s)
Anti-Bacterial Agents/chemistry , Coriandrum/chemistry , Plant Extracts/chemistry , Silver/chemistry , Gram-Negative Bacteria/drug effects , Ligands , Metal Nanoparticles/chemistry , Microbial Sensitivity Tests , Microscopy, Electron, Transmission , Plant Leaves/chemistry , Seeds/chemistry , Spectrophotometry, Ultraviolet , Spectroscopy, Fourier Transform Infrared , Spectrum Analysis, Raman , X-Ray Diffraction
5.
Med Mycol ; 53(5): 505-11, 2015 Jun.
Article in English | MEDLINE | ID: mdl-25980003

ABSTRACT

Trichosporon asahii is considered an opportunistic pathogen responsible for severe infections, mainly in immunocompromised patients. The aims of this study were to investigate the prevalent genotypes among 39 clinical isolates of this microorganism by sequencing the IGS1 region and to determine the in vitro production of DNAse, hemolysin, aspartyl proteinase, phospholipase and esterase, as well as the susceptibilities of the isolates to amphotericin B, anidulafungin, micafungin, caspofungin, voriconazole, posaconazole, fluconazole and 5-flucytosine. Our findings showed that genotype I was the most prevalent comprising 69.23% of the isolates. We confirmed the production of esterase for all our isolates, and report the production of DNAse and aspartyl proteinase in 84.62% and 23% of the isolates, respectively. Only one isolate of T. asahii produced hemolysin. None of the isolates showed phospholipase activity. Fifty-three percent of the T. asahii strains exhibited amphotericin B MICs ≥ 2 µg/ml. The three echinocandins evaluated yielded high MICs (≥2 µg/ml) in all isolates. Thirty-five percent of the isolates had high MICs for 5-flucytosine (≥32 µg/ml), and 97% of the isolates were susceptible to the evaluated triazoles.


Subject(s)
Antifungal Agents/pharmacology , Molecular Typing , Mycological Typing Techniques , Trichosporon/classification , Trichosporon/metabolism , Trichosporonosis/microbiology , Virulence Factors/metabolism , Genotype , Genotyping Techniques , Hemolysin Proteins/metabolism , Humans , Hydrolases/metabolism , Mexico , Microbial Sensitivity Tests , Sequence Analysis, DNA , Trichosporon/drug effects , Trichosporon/isolation & purification
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