Novel hybrids of 1,2,3-triazole-benzoxazole: design, synthesis, and assessment of DprE1 enzyme inhibitors using fluorometric assay and computational analysis

J Enzyme Inhib Med Chem. 2024 Dec;39(1):2403744. doi: 10.1080/14756366.2024.2403744. Epub 2024 Sep 27.

Abstract

Decaprenylphosphoryl-β-D-ribose-oxidase (DprE1), a subunit of the essential decaprenylphosphoribose-2'-epimerase, plays a crucial role in the synthesis of cell wall arabinan components in mycobacteria, including the pathogen responsible for tuberculosis, Mycobacterium tuberculosis. In this study, we designed, synthesised, and evaluated 15 (BOK-1-BOK-10 and BOP-1-BOP-5) potential inhibitors of DprE1 from a series of 1,2,3-triazole ligands using a validated DprE1 inhibition assay. Two compounds, BOK-2 and BOK-3, demonstrated significant inhibition with IC50 values of 2.2 ± 0.1 and 3.0 ± 0.6 μM, respectively, whereas the standard drug (TCA-1) showed inhibition at 3.0 ± 0.2 μM. Through molecular modelling and dynamic simulations, we explored the structural relationships between selected 1,2,3-triazole compounds and DprE1, revealing key features for effective drug-target interactions. This study introduces a novel approach for designing ligands against DprE1, offering a potential therapeutic strategy for tuberculosis treatment.

Keywords: 1,2,3-triazoles; DprE1 inhibitor assay; Tuberculosis.

Plain language summary

Identification of 15 (BOK-1–BOK-10 and BOP-1–BOP-5) potent inhibitors of DprE1 enzyme from 1,2,3-triazole ligands.BOK-2 and BOK-3 exhibited significant DprE1 inhibition with IC50 values of 2.2 ± 0.1 and 3.0 ± 0.6 μM, respectively.Molecular modelling and dynamic simulations elucidated key structural features for effective drug–target interactions.Novel approach introduced for designing DprE1 ligands, potentially aiding tuberculosis treatment.Findings offer promising candidates for future tuberculosis research.

MeSH terms

  • Alcohol Oxidoreductases / antagonists & inhibitors
  • Alcohol Oxidoreductases / metabolism
  • Bacterial Proteins / antagonists & inhibitors
  • Bacterial Proteins / metabolism
  • Benzoxazoles* / chemical synthesis
  • Benzoxazoles* / chemistry
  • Benzoxazoles* / pharmacology
  • Dose-Response Relationship, Drug*
  • Drug Design*
  • Enzyme Inhibitors* / chemical synthesis
  • Enzyme Inhibitors* / chemistry
  • Enzyme Inhibitors* / pharmacology
  • Fluorometry
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Mycobacterium tuberculosis* / drug effects
  • Mycobacterium tuberculosis* / enzymology
  • Structure-Activity Relationship
  • Triazoles* / chemical synthesis
  • Triazoles* / chemistry
  • Triazoles* / pharmacology

Substances

  • Triazoles
  • Benzoxazoles
  • Enzyme Inhibitors
  • DprE1 protein, Mycobacterium tuberculosis
  • Bacterial Proteins
  • Alcohol Oxidoreductases

Grants and funding

Funding has been awarded as follows: Personal Research Chair from Mr. James Bardrick, G.S.B. Medical Research Council MR/S000542/1, G.S.B. Medical Research Council MR/R001154/1, G.S.B. JSS Research Grant REG/DIR(R)/URG/54/2011–12/5293, M.S.