Journal
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
Volume 23, Issue 6, Pages 1174-1185Publisher
SOC BRASILEIRA QUIMICA
Keywords
oncocalyxone A; spectroelectrochemical-electron spin resonance; DNA interaction; N-acetylcysteine; Michael acceptor
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Funding
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES)
- PROCAD/NF (CAPES)
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq/PROSUL)
- INCT-Bioanalitica
- Programa de Apoio a Nucleos de Excelencia/Fundacao de Amparo a Pesquisa do Estado de. Alagoas (PRONEX/FAPEAL)
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The formation of paramagnetic species from oncocalyxone A in aprotic medium was confirmed by performing in situ electrochemical-electron spin resonance (E-ESR) experiments. The high delocalization of the radical generated at the first reduction potential is clearly evidenced by the hyperfine coupling of H-9 with the larger coupling constant, besides the couplings at the H-3 (close to quinone) and H-7 (far from the quinone nucleus) positions. In protic medium, together with pH dependence experiments, oncocalyxone A showed to be DNA-reactive through experiments with DNA sensors. Its reaction with N-acetylcysteine, with structural characterization of the addition products, proved its ability as Michael acceptor. Both aspects are important in terms of biological/pharmacological activities and indicate the present models as important tools in the screening of biologically active compounds.
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