Optimizing the flavanone core toward new selective nitrogen-containing modulators of ABC transporters

Ricardo J. Ferreira, Rafael Baptista, Alexis Moreno, Patricia G Madeira, Ruttiros Khonkarn, Hélène Baubichon-Cortay, Daniel Jva Dos Santos, Pierre Falson, Maria-José U Ferreira

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AIM: Naringenin (1), isolated in large amount from the aerial parts of Euphorbia pedroi, was chemically derivatized to yield 18 imine derivatives (2-19) and three alkylated derivatives through a Mannich-type reaction (20-22) that were tested as multidrug resistance (MDR) reversers in cancer cells. Results/methodology: While hydrazone (2-4) and azine (5-13) derivatives showed an improvement in their MDR reversal activities against the breast cancer resistance protein, carbohydrazides 14-19 revealed an enhancement in MDR reversal activity toward the multidrug resistance protein 1.

CONCLUSION: The observed activities, together with pharmacophoric analysis and molecular docking studies, identified the spatial orientation of the substituents as a key structural feature toward a possible mechanism by which naringenin derivatives may reverse MDR in cancer.

Original languageEnglish
JournalFuture Medicinal Chemistry
Issue number7
Early online date23 Mar 2018
Publication statusPublished - 01 Apr 2018
Externally publishedYes


  • ABC transporters
  • BCRP
  • flavanone
  • hydrazides
  • hydrazones
  • molecular docking
  • MRP1
  • multidrug resistance
  • P-gp
  • pharmacophore


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