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

Journal: Bioorganic & medicinal chemistry letters
PMID:

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 (M). 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 M 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 r exceeding 0.98 and an RMSE 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 IC values. The designed compounds exhibited suitable drug-like characteristics and adopted an active conformation similar to ebselen, inhibiting M 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.

Authors

  • Borwornlak Toopradab
    Program in Bioinformatics and Computational Biology, Graduate School, Chulalongkorn University, Bangkok 10330, Thailand; Center of Excellence in Biocatalyst and Sustainable Biotechnology, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
  • Wanting Xie
    Research Center of Nano Science and Technology, Department of Chemistry, College of Science, Shanghai University, Shanghai, 200444 PR China.
  • Lian Duan
    Department of Medical Informatics, Nantong University, Nantong, Jiangsu, China.
  • Kowit Hengphasatporn
    Center for Computational Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan.
  • Ryuhei Harada
    Center for Computational Sciences (CCS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan.
  • Silpsiri Sinsulpsiri
    Center of Excellence in Biocatalyst and Sustainable Biotechnology, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
  • Yasuteru Shigeta
    Center for Computational Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan.
  • Liyi Shi
    Research Center of Nano Science and Technology, Department of Chemistry, College of Science, Shanghai University, Shanghai, 200444 PR China; Emerging Industries Institute Shanghai University, Jiaxing, Zhejiang 314006, PR China.
  • Phornphimon Maitarad
    Research Center of Nano Science and Technology, Department of Chemistry, College of Science, Shanghai University, Shanghai, 200444 PR China. Electronic address: pmaitarad@shu.edu.cn.
  • Thanyada Rungrotmongkol
    Program in Bioinformatics and Computational Biology, Graduate School, Chulalongkorn University, Bangkok 10330, Thailand.