Piperidinyl-embeded chalcones possessing anti PI3Kδ inhibitory properties exhibit anti-atopic properties in preclinical models

Eur J Med Chem. 2018 Oct 5:158:405-413. doi: 10.1016/j.ejmech.2018.09.033. Epub 2018 Sep 12.

Abstract

Phosphatidylinositide 3-kinases (PI3Ks) are widely expressed enzymes involved in membrane signalization pathways. Attempts to administer inhibitors with broad activity against different isoforms have failed due to toxicity. Conversely the PI3Kδ isoform is much more selectively expressed, enabling therapeutic targeting of this isoform. Of particular interest PI3Kδ is expressed in human basophils and its inhibition has been shown to reduce anti-IgE induced basophil degranulation, suggesting that PI3Kδ inhibitors could be useful as anti-allergy drugs. Herein, we report for the first time the activity of compounds derived from chalcone scaffolds as inhibitors of normal human basophil degranulation and identified the most active compound with anti-PI3Kδ properties that was investigated in preclinical models. Compound 18, namely 1-[2-hydroxy-4,6-dimethoxy-3-(N-methylpiperidin-4-yl)phenyl]-3-(2,4,6-trimethoxyphenyl)-prop-2-en-1-one, was found to inhibit normal human basophil degranulation in a dose-dependent manner. In a murine model of ovalbumin-induced asthma, compound 18 was shown to reduce expiratory pressure while its impact on the inflammatory infiltrate in alveolar lavage and total lung was dependent on the route of administration. In a DNFB-induced model of atopic dermatitis compound 18 administered systemically proved to be as potent as topical betamethasone. These results support the anti-atopic and allergic properties of the title compound and warrant further clinical development.

Keywords: Allergic properties; Anti-atopic activity; Basophil degranulation; Chalcones; PI3Kδ.

MeSH terms

  • Animals
  • Asthma / drug therapy
  • Asthma / metabolism
  • Basophils / drug effects*
  • Basophils / physiology
  • Cell Degranulation / drug effects
  • Chalcones / chemistry*
  • Chalcones / pharmacology*
  • Chalcones / therapeutic use
  • Dermatitis, Atopic / drug therapy*
  • Dermatitis, Atopic / metabolism
  • Disease Models, Animal
  • Drug Evaluation, Preclinical
  • Humans
  • Mice
  • Models, Molecular
  • Phosphatidylinositol 3-Kinases / metabolism
  • Phosphoinositide-3 Kinase Inhibitors*
  • Piperidines / chemistry
  • Piperidines / pharmacology
  • Piperidines / therapeutic use
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / pharmacology*
  • Protein Kinase Inhibitors / therapeutic use

Substances

  • Chalcones
  • Phosphoinositide-3 Kinase Inhibitors
  • Piperidines
  • Protein Kinase Inhibitors