Study of Reactions of Two Mannich Bases Derived of 4'-Hydroxychalcones with Glutathione by RP-TLC, RP-HPLC and RP-HPLC-ESI-MS Analysis
AUTOR(ES)
Bernardes, Aline, Pérez, Caridad N., Mayer, Mátyás, Silva, Cameron C. da, Martins, Felipe T., Perjési, Pál
FONTE
J. Braz. Chem. Soc.
DATA DE PUBLICAÇÃO
2017-06
RESUMO
4'-Hydroxychalcones have been reported to possess several beneficial biological effects. Several lines of evidence accumulated to demonstrate increased biological activities of the Mannich base derivatives of the parent 4'-hydroxychalcones. Bioactivities of chalcones and related α,β-unsaturated ketones are frequently associated with their reactivity with cellular thiols, such as GSH. For comparison of GSH reactivity, two bis Mannich bases of two 4'-hydroxychalcones were synthesized and reacted with GSH under non-cellular conditions. Reversed-phase thin layer chromatography (RP-TLC) and reversed-phase high performance liquid chromatography (RP-HPLC) analysis showed formation of two polar products which structures were confirmed by RP-HPLC-ESI-MS (RP-HPLC-electrospray ionization mass spectrometry) as 1:1 chalcone-GSH adducts in each case. At pH values below 8.0, the two bis Mannich bases showed higher GSH reactivity than two 4'-hydroxychalcones. Influence of the nature of the amino groups, the ring-B substituents and pH of the medium on reactivity was also investigated. The findings could serve as useful structure-activity information for subsequent molecular modification of thiol-reactive 4'-hydroxychalcones.
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