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1.
Bioorg Chem ; 110: 104786, 2021 05.
Artículo en Inglés | MEDLINE | ID: mdl-33740676

RESUMEN

Studies displaying the combination of mefloquine (MFL) with anti-tuberculosis (TB) substances are limited in the literature. In this work, the effect of MFL-association with two first-line anti-TB drugs and six fluoroquinolones was evaluated against Mycobacterium tuberculosis drug resistant strains. MFL showed synergistic interaction with isoniazid, pyrazinamide, and several fluoroquinolones, reaching fractional inhibitory concentration indexes (FICIs) ranging from 0.03 to 0.5. In order to better understand the observed results, two approaches have been explored: (i) spectroscopic responses attributed to the effect of MFL on physicochemical properties related to a liposomal membrane model composed by soybean asolectin; (ii) molecular dynamics (MD) simulation data regarding MFL interaction with a membrane model based on PIM2, a lipid constituent of the mycobacterial cell wall. FTIR and NMR data showed that MFL affects expressively the region between the phosphate and the first methylene groups of soybean asolectin membranes, disordering these regions. MD simulations results detected high MFL density in the glycolipid interface and showed that the drug increases the membrane lateral diffusion, enhancing its permeability. The obtained results suggest that synergistic activities related to MFL are attributed to its effect of lipid disorder and membrane permeability enhancement.


Asunto(s)
Antituberculosos/farmacología , Mefloquina/farmacología , Simulación de Dinámica Molecular , Mycobacterium tuberculosis/efectos de los fármacos , Antituberculosos/síntesis química , Antituberculosos/química , Relación Dosis-Respuesta a Droga , Espectroscopía de Resonancia Magnética , Mefloquina/síntesis química , Mefloquina/química , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Isótopos de Fósforo , Espectroscopía Infrarroja por Transformada de Fourier , Relación Estructura-Actividad
2.
Chem Phys Lipids ; 225: 104828, 2019 12.
Artículo en Inglés | MEDLINE | ID: mdl-31550456

RESUMEN

Regarding free genistein small delivery to the central nervous system, physico-chemical parameters of dimiristoylphosphatidylcholine liposome-loaded genistein were investigated, as well as its in vitro activity against the DPPH radical and glioma cells. Data obtained by UV-vis spectroscopy, Fourier Transform Infrared Spectroscopy, Nuclear Magnetic Resonance, Differential Scanning Calorimetry and Dynamic Light Scattering were used to characterize the liposomal system with respect to motion restriction, hydration degree, trans-gauche isomerization and phase state. In vitro antitumoral effects were monitored through conting and viability assays. Genistein hydroxyl group and lipid hydrogen bonds may have important role in dimiristoylphosphatidylcholine phosphate and choline motion restriction. Genistein-induced choline restriction may be also related to a decrease in the group rotation rate. Genistein: dimiristoylphosphatidylcholine system showed higher molecular package at the acyl chains region compaired to empty liposomes, and it may be related to a decrease in gauche bonds quantity and system size. Lipid acyl chain length seems to influence different genistein effects on membranes, due to the presence of gauche conformers. Genistein: dimiristoylphosphatidylcholine liposome was more efficient as DPPH reducting system than the free-Gen. Liposomal system, at genistein 100 µM, was so efficient as the correspondent free-form genistein, probably showing higher stability to cross the blood-brain barrier. Genistein and the lipid did not show an additive activity against glioma cells. Antioxidant and anti-glioma genistein-loaded liposome potential may be related to the isoflavone location and its restriction effect in the lipid molecular motion. Anti-glioma activity may also be related to a decrease of system size and trans-gauche isomerization.


Asunto(s)
Antineoplásicos/farmacología , Antioxidantes/farmacología , Sistemas de Liberación de Medicamentos , Genisteína/farmacología , Glioma/tratamiento farmacológico , Fosfatidilcolinas/farmacología , Animales , Antineoplásicos/química , Antioxidantes/química , Compuestos de Bifenilo/antagonistas & inhibidores , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Genisteína/química , Glioma/metabolismo , Glioma/patología , Estructura Molecular , Fosfatidilcolinas/química , Picratos/antagonistas & inhibidores , Ratas , Relación Estructura-Actividad , Células Tumorales Cultivadas
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