Discovery of Potent Inhibitors against P-Glycoprotein-Mediated Multidrug Resistance Aided by Late-Stage Functionalization of a 2-(4-(Pyridin-2-yl)phenoxy)pyridine Analogue

J Med Chem. 2020 May 28;63(10):5458-5476. doi: 10.1021/acs.jmedchem.0c00337. Epub 2020 May 7.

Abstract

SIS3 is a specific inhibitor of Smad3 that inhibits the TGFβ1-induced phosphorylation of Smad3. In this article, a variety of SIS3 derivatives were designed and synthesized to discover potential inhibitors against P-glycoprotein-mediated multidrug resistance aided by late-stage functionalization of a 2-(4-(pyridin-2-yl)phenoxy)pyridine analogue. A novel class of potent P-gp reversal agents were investigated, and a lead compound 37 was identified as a potent P-gp reversal agent with strong bioactivity and outstanding affinity for P-gp.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B / antagonists & inhibitors
  • ATP Binding Cassette Transporter, Subfamily B / metabolism
  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / antagonists & inhibitors*
  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / metabolism
  • Animals
  • Drug Discovery / methods*
  • Drug Resistance, Multiple / drug effects*
  • Drug Resistance, Multiple / physiology
  • Humans
  • Isoquinolines / chemistry*
  • Isoquinolines / metabolism
  • Isoquinolines / pharmacology*
  • K562 Cells
  • Mice
  • Mice, Inbred BALB C
  • Mice, Nude
  • Molecular Docking Simulation / methods
  • Pyridines / chemistry*
  • Pyridines / metabolism
  • Pyridines / pharmacology*
  • Pyrroles / chemistry*
  • Pyrroles / metabolism
  • Pyrroles / pharmacology*
  • Smad3 Protein / antagonists & inhibitors
  • Smad3 Protein / metabolism
  • Xenograft Model Antitumor Assays / methods

Substances

  • 6,7-dimethyl-2-(2E)-3-(1-methyl-2-phenyl-1H-pyrrolo(2,3-b)pyridin-3-yl-prop-2-enoyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride
  • ABCB1 protein, human
  • ATP Binding Cassette Transporter, Subfamily B
  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Isoquinolines
  • Pyridines
  • Pyrroles
  • Smad3 Protein