Abstract <p>The increasing global health concerns posed by <i>Mycobacterium tuberculosis</i> (<i>MTb</i>) necessitates the development of novel therapeutic agents targeting essential and host-absent biochemical pathways. This study explores a novel series of thiazetidine derivatives as potential inhibitors against two crucial enzymes of the <i>MTb</i>’s shikimate pathway: chorismate mutase (CM) and shikimate kinase (SK). Their interactions with CM and SK were characterized following different experimental and computational approaches. Experimental binding assays revealed strong affinities, particularly for compounds <b>4&#xa0;g (</b>Kd<b> = </b>1.23&#xa0;µM<b>)</b> and <b>4&#xa0;m</b> (0.60&#xa0;µM<b>)</b> with CM and <b>4&#xa0;l</b> (0.17&#xa0;µM) and <b>4o</b> (0.41&#xa0;µM) with SK. Computational modeling has identified <b>4&#xa0;g</b> (− 5.544&#xa0;kcal&#xa0;mol<sup>−1</sup>) and <b>4&#xa0;m</b> (− 5.044&#xa0;kcal&#xa0;mol<sup>−1</sup>) (for CM) and <b>4&#xa0;l</b> (− 4.454&#xa0;kcal&#xa0;mol<sup>−1</sup>) and <b>4o</b> (− 4.248&#xa0;kcal&#xa0;mol<sup>−1</sup>) (for SK) as the strongest binders, with subsequent MD simulations confirming the stability and structural integrity of the above lead complexes. Further the minimum inhibitory concentrations of all the derivatives were evaluated experimentally by monitoring the growth inhibition potentials against live <i>MTb</i> cells. <b>4&#xa0;g</b> and <b>4&#xa0;m</b> revealed the best MIC values of 8.35 and 0.7 <InlineEquation ID="IEq1"> <EquationSource Format="TEX">\(\mu \)</EquationSource> </InlineEquation> M respectively. These findings validate the thiazetidine scaffold as a potent framework for inhibiting the <i>MTb</i> shikimate pathway, positioning derivatives <b>4&#xa0;g, 4&#xa0;m, 4&#xa0;l</b> and <b>4o</b> as highly promising lead compounds for future rational anti-tuberculosis drug development.</p> Graphical abstract <p></p>

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An integrated in silico and in vitro approach to decipher the anti-tubercular potential of novel thiazetidine scaffolds

  • N. Thansila Parvin,
  • Kaushik Chanda,
  • M. M. Balamurali

摘要

Abstract

The increasing global health concerns posed by Mycobacterium tuberculosis (MTb) necessitates the development of novel therapeutic agents targeting essential and host-absent biochemical pathways. This study explores a novel series of thiazetidine derivatives as potential inhibitors against two crucial enzymes of the MTb’s shikimate pathway: chorismate mutase (CM) and shikimate kinase (SK). Their interactions with CM and SK were characterized following different experimental and computational approaches. Experimental binding assays revealed strong affinities, particularly for compounds 4 g (Kd = 1.23 µM) and 4 m (0.60 µM) with CM and 4 l (0.17 µM) and 4o (0.41 µM) with SK. Computational modeling has identified 4 g (− 5.544 kcal mol−1) and 4 m (− 5.044 kcal mol−1) (for CM) and 4 l (− 4.454 kcal mol−1) and 4o (− 4.248 kcal mol−1) (for SK) as the strongest binders, with subsequent MD simulations confirming the stability and structural integrity of the above lead complexes. Further the minimum inhibitory concentrations of all the derivatives were evaluated experimentally by monitoring the growth inhibition potentials against live MTb cells. 4 g and 4 m revealed the best MIC values of 8.35 and 0.7 \(\mu \) M respectively. These findings validate the thiazetidine scaffold as a potent framework for inhibiting the MTb shikimate pathway, positioning derivatives 4 g, 4 m, 4 l and 4o as highly promising lead compounds for future rational anti-tuberculosis drug development.

Graphical abstract