Identification of para-Substituted Benzoic Acid Derivatives as Potent Inhibitors of the Protein Phosphatase Slingshot

ChemMedChem. 2015 Dec;10(12):1980-7. doi: 10.1002/cmdc.201500454. Epub 2015 Nov 10.

Abstract

Slingshot proteins form a small group of dual-specific phosphatases that modulate cytoskeleton dynamics through dephosphorylation of cofilin and Lim kinases (LIMK). Small chemical compounds with Slingshot-inhibiting activities have therapeutic potential against cancers or infectious diseases. However, only a few Slingshot inhibitors have been investigated and reported, and their cellular activities have not been examined. In this study, we identified two rhodanine-scaffold-based para-substituted benzoic acid derivatives as competitive Slingshot inhibitors. The top compound, (Z)-4-((4-((4-oxo-2-thioxo-3-(o-tolyl)thiazolidin-5-ylidene)methyl)phenoxy)methyl)benzoic acid (D3) had an inhibition constant (Ki) of around 4 μm and displayed selectivity over a panel of other phosphatases. Moreover, compound D3 inhibited cell migration and cofilin dephosphorylation after nerve growth factor (NGF) or angiotensin II stimulation. Therefore, our newly identified Slingshot inhibitors provide a starting point for developing Slingshot-targeted therapies.

Keywords: Slingshot; anticancer; cell migration; nerve growth factor (NGF); phosphatase inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzoates / chemistry*
  • Benzoates / metabolism
  • Benzoates / pharmacology
  • Benzoic Acid / chemistry*
  • Benzoic Acid / metabolism
  • Benzoic Acid / pharmacology
  • Cell Movement / drug effects
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Inhibitory Concentration 50
  • Kinetics
  • Lim Kinases / metabolism
  • Nerve Growth Factor / pharmacology
  • PC12 Cells
  • Phosphoprotein Phosphatases / antagonists & inhibitors*
  • Phosphoprotein Phosphatases / metabolism
  • Phosphorylation / drug effects
  • Protein Binding
  • Rats
  • Rhodanine / analogs & derivatives*
  • Rhodanine / chemistry
  • Rhodanine / metabolism
  • Rhodanine / pharmacology
  • Structure-Activity Relationship

Substances

  • 4-((4-((4-oxo-2-thioxo-3-(o-tolyl)thiazolidin-5-ylidene)methyl)phenoxy)methyl)benzoic acid
  • Benzoates
  • Enzyme Inhibitors
  • Rhodanine
  • Benzoic Acid
  • Nerve Growth Factor
  • Lim Kinases
  • Phosphoprotein Phosphatases