Browsing by Author "Flores, Mario E."

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    Approach to Circular Chemistry Preparing New Polyesters from Olive Oil
    (2023) Werlinger, Francisca; Caprile, Renato; Cardenas-Toledo, Valentino; Tarraff, Bastian; Mesias-Salazar, Angela; Rojas, Rene S.; Martinez, Javier; Trofymchuk, Oleksandra S.; Flores, Mario E.
    The transformation of cooking oils and their waste intopolyestersis a challenge for circular chemistry. Herein, we have used epoxidizedolive oil (EOO), obtained from cooking olive oil (COO), and variouscyclic anhydrides (such as phthalic anhydride PA, maleic anhydrideMA, and succinic anhydride SA) as raw materials for the preparationof new bio-based polyesters. For the synthesis of these materials,we have used the bis(guanidine) organocatalyst 1 andtetrabutylammonium iodide (Bu4NI) as cocatalyst. The optimalreaction conditions for the preparation of poly(EOO-co-PA) and poly(EOO-co-MA) were 80 degrees C for 5 husing toluene as solvent; however, the synthesis of poly(EOO-co-SA) required more extreme reaction conditions. Furthermore,we have exclusively succeeded in obtaining the trans isomer for MA-polyester.The obtained biopolyesters were characterized by NMR, Fourier transforminfrared, thermogravimetric analysis, and scanning electron microscopyanalyses. Since there are few examples of functionalized and definedcompounds based on olive oil, it is innovative and challenging totransform these natural-based compounds into products with high addedvalue.
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    Colloidal nanomedicines with prolonged release of chloroquine based on interactions with aromatic polymers after mixing two liquids: from in silico simulation of nanoparticle formation to efficient in-bench scale up
    (2024) Villamizar-Sarmiento, Maria Gabriela; Yanez, Osvaldo; Flores, Mario E.; Alvarez-Acevedo, Gonzalo; Gonzalez-Nilo, Fernando; Guerrero, Juan; Moreno-Villoslada, Ignacio; Oyarzun-Ampuero, Felipe A.
    Nanomedicines containing the aromatic drug chloroquine and the polymer poly(sodium 4-styrenesulfonate) have been theoretically designed and experimentally synthesized following the simple mixture of two aqueous solutions containing the drug and the polymer, respectively. Theoretical calculations show higher binding energy between both the aromatic polymer and chloroquine, and a higher tendency to release water from their hydration spheres, as compared to the binding between the drug and the aliphatic polymer poly(sodium vinyl sulfonate). MD simulations show the spontaneous formation of stable structures of 10 nm of average diameter, even combining short polymer chains, highly diluted reactants, and short reaction time (in the range of mu s). Rapid mixture of the liquids in a stopped flow equipment shows nanoparticle formation in the range of tenths of seconds. Equilibration studies in the range of minutes evidence spheroidal nanoparticles with almost quantitative association efficiency, 48.6 % of drug loading, size of 170 - 410 nm, low polydispersity (PdI = 0.25 - 0.47), and negative zeta potential (-18 - -45 mV). They provide drug release for 30 days, and are stable to NaCl exposure, pH gradient, several temperature values, and long-term storage. Furthermore, we demonstrate scaling up of the nanomedicine production upon increasing the reaction volume. Our studies demonstrate that these highly loaded drug nanoparticles are based on the occurrence of site -specific short-range interactions between the drug and the aromatic excipient such as pi-stacking. In the absence of the aromatic group in the polymer, weak interactions and unstable formulations are evidenced, both theoretically and experimentally. The combination of the selected theoretical and experimental tools could promote the efficient production of drug / polyelectrolyte formulations with therapeutical applications. The chosen components could be considered as potential medicines or as model components to design, develop, characterize, and scale up medicines comprising other combinations of drugs and polymers.
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    Effect of Polymer Micelles on Antifungal Activity of Geranylorcinol Compounds against Botrytis cinerea
    (2015) Taborga, Lautaro.; Reyes Bravo, Paula Verónica; Díaz, Katy.; Olea, Andrés F.; Flores, Mario E.; Peña Cortés, Hugo.; Espinoza Catalán, Luis Javier.