Allosteric inhibition of tRNA synthetase Gln4 by N-pyrimidinyl-β-thiophenylacrylamides exerts highly selective antifungal activity Journal Articles uri icon

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abstract

  • Candida species are among the most prevalent causes of systemic fungal infections, which account for ∼1.5 million annual fatalities. Here, we build on a compound screen that identified the molecule N-pyrimidinyl-β-thiophenylacrylamide (NP-BTA), which strongly inhibits Candida albicans growth. NP-BTA was hypothesized to target C. albicans glutaminyl-tRNA synthetase, Gln4. Here, we confirmed through in vitro amino-acylation assays NP-BTA is a potent inhibitor of Gln4, and we defined how NP-BTA arrests Gln4's transferase activity using co-crystallography. This analysis also uncovered Met496 as a critical residue for the compound's species-selective target engagement and potency. Structure-activity relationship (SAR) studies demonstrated the NP-BTA scaffold is subject to oxidative and non-oxidative metabolism, making it unsuitable for systemic administration. In a mouse dermatomycosis model, however, topical application of the compound provided significant therapeutic benefit. This work expands the repertoire of antifungal protein synthesis target mechanisms and provides a path to develop Gln4 inhibitors.

authors

  • Puumala, Emily
  • Sychantha, David
  • Lach, Elizabeth
  • Reeves, Shawn
  • Nabeela, Sunna
  • Fogal, Meea
  • Nigam, AkshatKumar
  • Johnson, Jarrod W
  • Aspuru-Guzik, Alán
  • Shapiro, Rebecca S
  • Uppuluri, Priya
  • Kalyaanamoorthy, Subha
  • Magolan, Jakob
  • Whitesell, Luke
  • Robbins, Nicole
  • Wright, Gerard
  • Cowen, Leah E

publication date

  • April 2024