Rational design of isonicotinic acid hydrazide derivatives with antitubercular activity: Machine learning, molecular docking, synthesis and biological testing

Chem Biol Drug Des. 2018 Jul;92(1):1272-1278. doi: 10.1111/cbdd.13188. Epub 2018 May 6.

Abstract

The problem of designing new antitubercular drugs against multiple drug-resistant tuberculosis (MDR-TB) was addressed using advanced machine learning methods. As there are only few published measurements against MDR-TB, we collected a large literature data set and developed models against the non-resistant H37Rv strain. The predictive accuracy of these models had a coefficient of determination q2 = .7-.8 (regression models) and balanced accuracies of about 80% (classification models) with cross-validation and independent test sets. The models were applied to screen a virtual chemical library, which was designed to have MDR-TB activity. The seven most promising compounds were identified, synthesized and tested. All of them showed activity against the H37Rv strain, and three molecules demonstrated activity against the MDR-TB strain. The docking analysis indicated that the discovered molecules could bind enoyl reductase, InhA, which is required in mycobacterial cell wall development. The models are freely available online (http://ochem.eu/article/103868) and can be used to predict potential anti-TB activity of new chemicals.

Keywords: Mycobacterium tuberculosis (Mtb); OCHEM; antitubercular activity; isonicotinic acid hydrazide derivatives; machine learning; molecular docking.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / pharmacology
  • Antitubercular Agents / therapeutic use
  • Bacterial Proteins / chemistry
  • Bacterial Proteins / metabolism
  • Binding Sites
  • Catalytic Domain
  • Drug Design*
  • Humans
  • Isoniazid / chemistry*
  • Isoniazid / pharmacology
  • Isoniazid / therapeutic use
  • Machine Learning
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation
  • Mycobacterium tuberculosis / drug effects
  • Mycobacterium tuberculosis / metabolism
  • Oxidoreductases / chemistry
  • Oxidoreductases / metabolism
  • Tuberculosis, Multidrug-Resistant / drug therapy
  • Tuberculosis, Multidrug-Resistant / pathology

Substances

  • Antitubercular Agents
  • Bacterial Proteins
  • Oxidoreductases
  • InhA protein, Mycobacterium
  • Isoniazid