ArticleCell chemical biology2021
Resistance of Mycobacterium tuberculosis to indole 4-carboxamides occurs through alterations in drug metabolism and tryptophan biosynthesis.
Article in Cell chemical biology, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed, 15 citations in OpenAlex.
- Synthesis of 4-Aminoindole-Containing Cephalosporin Prodrugs and Their Biological Activity againstACS infectious diseases · 2026Article
- The Quantification of Drug Accumulation within Gram-Negative Bacteria.ACS infectious diseases · 2026Article
- Systematic evaluation of computational tools to predict the effects of mutations on protein-ligand binding affinity in the absence of experimental structures.Briefings in bioinformatics · 2026Article
- Carboxamide: A Privileged Pharmacophore for the Development of Anti-infectious and Anti-cancer Drugs.Current topics in medicinal chemistry · 2026Review
- Design and synthesis of novel spirocyclic oxindole based hybrid scaffolds:RSC advances · 2025Article
- 5-Fluoroindole Reduces the Bacterial Burden in a Murine Model ofACS omega · 2024Article
- Amino Acid Biosynthesis Inhibitors in Tuberculosis Drug Discovery.Pharmaceutics · 2024Review
- Identification and optimization of pyridine carboxamide-based scaffold as a drug lead forAntimicrobial agents and chemotherapy · 2024Article
- A serum NMR metabolomic analysis of the Corynebacterium pseudotuberculosis infection in goats.Applied microbiology and biotechnology · 2023Article
- 6-Fluorophenylbenzohydrazides inhibit Mycobacterium tuberculosis growth through alteration of tryptophan biosynthesis.European journal of medicinal chemistry · 2021Article
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11 authors at 3 institutions in 3 countries.
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Abstract
Tryptophan biosynthesis represents an important potential drug target for new anti-TB drugs. We identified a series of indole-4-carboxamides with potent antitubercular activity. In vitro, Mycobacterium tuberculosis (Mtb) acquired resistance to these compounds through three discrete mechanisms: (1) a decrease in drug metabolism via loss-of-function mutations in the amidase that hydrolyses these carboxamides, (2) an increased biosynthetic rate of tryptophan precursors via loss of allosteric feedback inhibition of anthranilate synthase (TrpE), and (3) mutation of tryptophan synthase (TrpAB) that decreased incorporation of 4-aminoindole into 4-aminotryptophan. Thus, these indole-4-carboxamides act as prodrugs of a tryptophan antimetabolite, 4-aminoindole.
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