Design and Synthesis of Highly Potent and Specific ABHD6 Inhibitors

ChemMedChem. 2023 Nov 2;18(21):e202100406. doi: 10.1002/cmdc.202100406. Epub 2021 Sep 6.

Abstract

Fine-tuning than complete disruption of 2-arachidonoylglycerol (2-AG) metabolism in the brain represents a promising pharmacological approach to limit potential untoward effects associated with complete blockade of monoacylglycerol lipase (MGL), the primary hydrolase of 2-AG. This could be achieved through a/b-hydrolase domain containing 6 (ABHD6) inhibition, which will provide a smaller and safer contribution to 2-AG regulation in the brain. Pharmacological studies with ABHD6 inhibitors have recently been reported, where modulation of ABHD6 activity either through CB1R-dependent or CB1R-independent processes showed promise in preclinical models of epilepsy, neuropathic pain and inflammation. Furthermore in the periphery, ABHD6 modulates 2-AG and other fatty acid monoacylglycerols (MAGs) and is implicated in Type-2 diabetes, metabolic syndrome and potentially other diseases. Herein, we report the discovery of single-digit nanomolar potent and highly specific ABHD6 inhibitors with >1000-fold selectivity against MGL and FAAH. The new ABHD6 inhibitors provide early leads to develop therapeutics for neuroprotection and the treatment of inflammation and diabetes.

Keywords: monoacylglycerol lipase; neuroinflammation.; neuroprotection; α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid; α/β-hydrolase domain containing 6.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Diabetes Mellitus, Type 2* / drug therapy
  • Enzyme Inhibitors / pharmacology
  • Enzyme Inhibitors / therapeutic use
  • Humans
  • Hydrolases
  • Inflammation / drug therapy
  • Monoacylglycerol Lipases
  • Neuralgia* / drug therapy

Substances

  • Enzyme Inhibitors
  • Hydrolases
  • Monoacylglycerol Lipases
  • ABHD6 protein, human