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J Phys Chem A ; 124(19): 3865-3875, 2020 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-32285672


A broad series of quinoxalinone-based π-conjugated donor-acceptor fluoro- and NLO-phores is characterized by means of Raman spectroscopy and single-crystal X-ray analysis supported by quantum chemical computations. Intense Raman spectroscopic markers that allow the differentiation of even closely related structures are identified. The intensities of these bands are shown to be related to the conjugation of the different molecular moieties, and they can provide an estimation of its extent. The intensity redistribution between these markers serves as a source of auxiliary structural information capable of pointing to a distortion of the conjugation or to the influence of aggregation effects in the condensed state. A simple relation between the intensity of the marker and the position and oscillator strength of the lowest-energy electronic absorption band of quinoxalinones allows a linking of the Raman effect with the optical properties of these compounds, which can be used for the rational design of novel species with improved optical characteristics.

Bioorg Med Chem Lett ; 28(6): 1097-1100, 2018 04 01.
Artigo em Inglês | MEDLINE | ID: mdl-29459208


The mechanism of an antioxidant action of water-soluble polyol - methanofullerenes C60[C9H10O4(OH)4]6 and C60[C13H18O4(OH)4]6 as the mild uncouplers of an oxidative phosphorylation and respiration is postulated. According to this mechanism, hydroxyl group of methanofullerenols can be protonated under excess of protons in the intermembrane space of hyperpolarized mitochondria. Protonation of fullerene derivatives is confirmed by the decrease in their negative Zeta potential in the pH below 5.4. Heavily protonated methanofullerenols become positively charged and move into the mitochondrial matrix. As a consequence, the proton gradient is dissipated, which causes a decrease in mitochondrial transmembrane potential (ΔΨm) and reduction in ROS production.

Antioxidantes/farmacologia , Fulerenos/farmacologia , Mitocôndrias/efeitos dos fármacos , Polímeros/farmacologia , Antioxidantes/química , Relação Dose-Resposta a Droga , Fulerenos/química , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Estrutura Molecular , Polímeros/química , Solubilidade , Relação Estrutura-Atividade , Água/química
Bioorg Med Chem Lett ; 25(22): 5250-3, 2015 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-26483197


Here, we report for the first time on two novel water-soluble polyol-methanofullerenes which uncouple respiration and oxidative phosphorylation. A cytofluorimetric JC-1-based ratiometric assay was used to quantify mitochondrial potential Ψm in Yarrowia lipolytica cells exposed to the fullerenes tested. Both methanofullerenes significantly downregulated Ψm, thereby decreasing the subset of cells with high mitochondrial potential compared with intact control cells. The Ψm-low subset of Yarrowia lipolytica cells resulted from methanofullerenes exposure preserved physiological cell size and granularity patterns.

Fulerenos/farmacologia , Desacopladores/farmacologia , Yarrowia/efeitos dos fármacos , Citometria de Fluxo , Potenciais da Membrana , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/metabolismo , Fosforilação Oxidativa , Solubilidade , Água , Yarrowia/metabolismo