Machine learning-based QSAR and LB-PaCS-MD guided design of SARS-CoV-2 main protease inhibitors

Bioorg Med Chem Lett. 2024 Sep 15:110:129852. doi: 10.1016/j.bmcl.2024.129852. Epub 2024 Jun 24.

Abstract

The global outbreak of the COVID-19 pandemic caused by the SARS-CoV-2 virus had led to profound respiratory health implications. This study focused on designing organoselenium-based inhibitors targeting the SARS-CoV-2 main protease (Mpro). The ligand-binding pathway sampling method based on parallel cascade selection molecular dynamics (LB-PaCS-MD) simulations was employed to elucidate plausible paths and conformations of ebselen, a synthetic organoselenium drug, within the Mpro catalytic site. Ebselen effectively engaged the active site, adopting proximity to H41 and interacting through the benzoisoselenazole ring in a π-π T-shaped arrangement, with an additional π-sulfur interaction with C145. In addition, the ligand-based drug design using the QSAR with GFA-MLR, RF, and ANN models were employed for biological activity prediction. The QSAR-ANN model showed robust statistical performance, with an r2training exceeding 0.98 and an RMSEtest of 0.21, indicating its suitability for predicting biological activities. Integration the ANN model with the LB-PaCS-MD insights enabled the rational design of novel compounds anchored in the ebselen core structure, identifying promising candidates with favorable predicted IC50 values. The designed compounds exhibited suitable drug-like characteristics and adopted an active conformation similar to ebselen, inhibiting Mpro function. These findings represent a synergistic approach merging ligand and structure-based drug design; with the potential to guide experimental synthesis and enzyme assay testing.

Keywords: LB-PaCS-MD; Machine learning; Organoselenium; QSAR; SARS-CoV-2 main protease.

MeSH terms

  • Antiviral Agents* / chemical synthesis
  • Antiviral Agents* / chemistry
  • Antiviral Agents* / pharmacology
  • Azoles / chemical synthesis
  • Azoles / chemistry
  • Azoles / pharmacology
  • COVID-19 / virology
  • Catalytic Domain
  • Coronavirus 3C Proteases* / antagonists & inhibitors
  • Coronavirus 3C Proteases* / metabolism
  • Drug Design*
  • Humans
  • Isoindoles* / chemical synthesis
  • Isoindoles* / chemistry
  • Isoindoles* / pharmacology
  • Machine Learning*
  • Molecular Dynamics Simulation*
  • Organoselenium Compounds* / chemical synthesis
  • Organoselenium Compounds* / chemistry
  • Organoselenium Compounds* / pharmacology
  • Protease Inhibitors* / chemical synthesis
  • Protease Inhibitors* / chemistry
  • Protease Inhibitors* / pharmacology
  • Quantitative Structure-Activity Relationship*
  • SARS-CoV-2* / drug effects
  • SARS-CoV-2* / enzymology

Substances

  • Organoselenium Compounds
  • ebselen
  • Isoindoles
  • Coronavirus 3C Proteases
  • Protease Inhibitors
  • Antiviral Agents
  • Azoles