Discovery of Novel and Selective Adenosine A2A Receptor Antagonists for Treating Parkinson's Disease through Comparative Structure-Based Virtual Screening

J Chem Inf Model. 2017 Jun 26;57(6):1474-1487. doi: 10.1021/acs.jcim.7b00188. Epub 2017 May 15.

Abstract

Among non-dopaminergic strategies for combating Parkinson's disease (PD), antagonism of the A2A adenosine receptor (AR) has emerged to show great potential. In this study, on the basis of two crystal structures of the A2A AR with the best capability to distinguish known antagonists from decoys, docking-based virtual screening (VS) was conducted to identify novel A2A AR antagonists. A total of 63 structurally diverse compounds identified by VS were submitted to experimental testing, and 11 of them exhibited substantial activity against the A2A AR (Ki < 10 μM), including two compounds with Ki below 1 μM (compound 43, 0.42 μM; compound 51, 0.27 μM) and good A2A/A1 selectivity (fold < 0.1). Compounds 43 and 51 demonstrated antagonistic activity according to the results of cAMP measurements (cAMP IC50 = 1.67 and 1.80 μM, respectively) and showed good efficacy in the haloperidol-induced catalepsy (HIC) rat model for PD at doses of up to 30 mg/kg. Further lead optimization based on a substructure searching strategy led to the discovery of compound 84 as an excellent A2A AR antagonist (A2A Ki = 54 nM, A2A/A1 fold < 0.1, cAMP IC50 = 0.3 μM) that exhibited significant improvement in anti-PD efficacy in the HIC rat model.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine A2 Receptor Antagonists / chemistry*
  • Adenosine A2 Receptor Antagonists / pharmacology*
  • Adenosine A2 Receptor Antagonists / therapeutic use
  • Animals
  • Catalepsy / chemically induced
  • Catalepsy / drug therapy
  • Drug Evaluation, Preclinical / methods*
  • Haloperidol / pharmacology
  • Male
  • Models, Molecular
  • Molecular Conformation
  • Parkinson Disease / drug therapy*
  • Rats
  • Rats, Wistar
  • Receptor, Adenosine A2A / metabolism*
  • User-Computer Interface

Substances

  • Adenosine A2 Receptor Antagonists
  • Receptor, Adenosine A2A
  • Haloperidol