Study of reactions of two Mannich bases derived of 4′-hydroxychalcones with glutathione by RP-TLC, RP-HPLC and RP-HPLC-ESI-MS analysis

Aline Bernardes, Caridad N. Pérez, Mátyás Mayer, Cameron C. Da Silva, Felipe T. Martins, Pál Perjési

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1048-1062
Number of pages15
JournalJournal of the Brazilian Chemical Society
Volume28
Issue number6
DOIs
Publication statusPublished - Jun 1 2017

Keywords

  • Glutathione
  • Hydroxychalcones
  • Mannich bases
  • RP-HPLC-ESI-MS
  • RP-TLC

ASJC Scopus subject areas

  • Chemistry(all)

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