Browsing by Author "Trilleras, Jorge"

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    Furanyl chalcone derivatives as efficient singlet oxygen quenchers. An experimental and DFT/MRCI study
    (PERGAMON-ELSEVIER SCIENCE LTD, 2020) Diaz Uribe, Carlos; Vallejo, William; Florez, Jiress; Trilleras, Jorge; Gutierrez, Margarita; Rodriguez Serrano, Angela; Schott, Eduardo; Zarate, Ximena
    This study reports the antioxidant activity against singlet oxygen (O-1(2)) of five newly synthesized furanyl chalcones (FCs) (E)-3 (5-(4 chlorophenyl)furan-2-yl)-1-arylprop-2-en-1-ones (3a-e). Their structural difference is based on the aryl substituent as follows (Ar): 3a = -C6H4-OCH3, 3b = -C6H3-(1,2-OCH3), 3c = -C6H4OC6H4, 3d = - C10H6-(OCH3) and 3e = -C4H3O. We used a Claisen-Schmidt condensation involving a 5-(4-chlorophenyl)furan-2-carbaldehyde and the corresponding ketones under ultrasonic irradiation. Their property to O-1(2) quenching was analyzed in terms of the rate constant for the process (k(Q) at 25 degrees C) determined by the Stern-Volmer model in ethanol. For the compounds 3c, 3d and 3e, the k(Q) values are slightly larger respect to 3a and 3b. The FCs 3c behaves as the best quencher (k(Q )of 8.44 (+/- 0.09) x 10(7) M-1 s(-1)). Geometry analysis and electronic structure calculations have been performed in the framework of Density Functional Theory (DFT) and DFT/Multi-Reference Configuration Interaction (DFT/MRCI) methods. According to DFT/MRCI, a physical quenching of O-1(2) from the ground states of the FCs may not likely induce a spontaneous energy transfer processes but a chemical quenching mechanism may dominate the kinetics. (C) 2020 Elsevier Ltd. All rights reserved.
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    Synthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones
    (2024) Insuasty, Daniel; Mutis, Mario; Trilleras, Jorge; Illicachi, Luis A.; Rodriguez, Juan D.; Ramos-Hernandez, Andrea; San-Juan-Vergara, Homero G.; Cadena-Cruz, Christian; Mora, Jose R.; Paz, Jose L.; Mendez-Lopez, Maximiliano; Perez, Edwin G.; Aliaga, Margarita E.; Valencia, Jhesua; Marquez, Edgar
    In this article, three unsymmetrical 7-(diethylamino)quinolone chalcones with D-pi-A-D and D-pi-A-pi-D type push-pull molecular arrangements were synthesized via a Claisen-Schmidt reaction. Using 7-(diethylamino)quinolone and vanillin as electron donor (D) moieties, these were linked together through the alpha,beta-unsaturated carbonyl system acting as a linker and an electron acceptor (A). The photophysical properties were studied, revealing significant Stokes shifts and strong solvatofluorochromism caused by the ICT and TICT behavior produced by the push-pull effect. Moreover, quenching caused by the population of the TICT state in THF-H2O mixtures was observed, and the emission in the solid state evidenced a red shift compared to the emission in solution. These findings were corroborated by density functional theory (DFT) calculations employing the wb97xd/6-311G(d,p) method. The cytotoxic activity of the synthesized compounds was assessed on BHK-21, PC3, and LNCaP cell lines, revealing moderate activity across all compounds. Notably, compound 5b exhibited the highest activity against LNCaP cells, with an LC50 value of 10.89 mu M. Furthermore, the compounds were evaluated for their potential as imaging agents in living prostate cells. The results demonstrated their favorable cell permeability and strong emission at 488 nm, positioning them as promising candidates for cancer cell imaging applications.