A Lipophilic 4-Phenylbutyric Acid Derivative That Prevents Aggregation and Retention of Misfolded Proteins

Chemistry. 2020 Feb 6;26(8):1834-1845. doi: 10.1002/chem.201904292. Epub 2020 Jan 27.

Abstract

Chemical chaperones prevent protein aggregation. However, the use of chemical chaperones as drugs against diseases due to protein aggregation is limited by the very high active concentrations (mm range) required to mediate their effect. One of the most common chemical chaperones is 4-phenylbutyric acid (4-PBA). Despite its unfavorable pharmacokinetic properties, 4-PBA was approved as a drug to treat ornithine cycle diseases. Here, we report that 2-isopropyl-4-phenylbutanoic acid (5) has been found to be 2-10-fold more effective than 4-PBA in several in vitro models of protein aggregation. Importantly, compound 5 reduced the secretion rate of autism-linked Arg451Cys Neuroligin3 (R451C NLGN3).

Keywords: ER stress; aggregation; chaperones; lipophilicity; protein folding.

MeSH terms

  • Animals
  • Cell Adhesion Molecules, Neuronal / chemistry
  • Cell Adhesion Molecules, Neuronal / genetics
  • Cell Adhesion Molecules, Neuronal / metabolism
  • Cell Survival / drug effects
  • HEK293 Cells
  • Humans
  • Membrane Proteins / chemistry
  • Membrane Proteins / genetics
  • Membrane Proteins / metabolism
  • Mutagenesis, Site-Directed
  • Nerve Tissue Proteins / chemistry
  • Nerve Tissue Proteins / genetics
  • Nerve Tissue Proteins / metabolism
  • PC12 Cells
  • Phenylbutyrates / chemistry*
  • Phenylbutyrates / pharmacology
  • Protein Aggregates / drug effects
  • Protein Folding
  • Proteins / chemistry*
  • Proteins / metabolism
  • Rats

Substances

  • Cell Adhesion Molecules, Neuronal
  • Membrane Proteins
  • Nerve Tissue Proteins
  • Phenylbutyrates
  • Protein Aggregates
  • Proteins
  • neuroligin 3
  • 4-phenylbutyric acid