Synthesis and biological evaluation of curcumin-nitroxide-based molecular hybrids as antioxidant and anti-proliferative agents

Balázs Bognár, M. Lakshmi Kuppusamy, Esha Madan, T. Kalai, Mária Balog, J. Jekó́, Periannan Kuppusamy, K. Hideg

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Background: Natural products and their derivatives are widely used to treat cancer and other diseases associated with ROS- and RNS-induced damages. Methods: A series of paramagnetic modified curcumin analogs and 3,5-diarylidene-piperidones (DAP) have been designed, synthesized, and characterized on their anti-proliferative and antioxidant activity. Results: Biological characterization of the new compounds supported the earlier results that incorporation of a nitroxide moiety or its precursor into curcumin or diarylidenylpiperidone (DAP) scaffolds resulted in anti-proliferative effect toward cancerous cell-lines in case of aryl hydroxy and/or methoxy substituent containing derivatives, suggesting their potential for targeted therapeutic applications. In case of basic side chain derivatives, nitroxide incorporation gave unambiguous results, however in tendency the more accessible DAP derivatives had stronger anti-proliferative effect. In most cases, the nitroxide incorporation increased the TEAC value (proton and electron donation capability) of DAP derivatives. Conclusions: Among the compounds synthesized and investigated the spin-labeled curcumin and 3,5-bis(4-hydroxy-3-methoxybenzylidene)piperidin-4-one derivatives were the most effective anti-proliferative and antioxidant derivatives.

Original languageEnglish
Pages (from-to)761-772
Number of pages12
JournalMedicinal Chemistry
Volume13
Issue number8
DOIs
Publication statusPublished - Dec 1 2017

Keywords

  • Anti-proliferative compounds
  • Antioxidants
  • Curcuminoids
  • Nitroxides
  • Pabon reaction
  • Structure-activity relationship

ASJC Scopus subject areas

  • Drug Discovery

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