Synthesis of a New Purine Analogue Class with Antifungal Activity and Improved Potency against Fungal IP3-4K

ACS Infect Dis. 2025 Apr 11;11(4):940-953. doi: 10.1021/acsinfecdis.4c00975. Epub 2025 Mar 31.

Abstract

New antifungals are urgently needed to treat deadly fungal infections. Targeting the fungal inositol polyphosphate kinases IP3-4K (Arg1) and IP6K (Kcs1) is a promising strategy as it has been validated genetically to be crucial for fungal virulence but never pharmacologically. We now report the synthesis of DT-23, an analogue of N2-(m-trifluorobenzylamino)-N6-(p-nitrobenzylamino)purine (TNP), and demonstrate that it more potently inhibits recombinant Arg1 from the priority pathogen Cryptococcus neoformans (Cn) (IC50 = 0.6 μM) than previous analogues (IC50 = 10-30 μM). DT-23 also inhibits recombinant Kcs1 with similar potency (IC50 = 0.68 μM) and Arg1 and Kcs1 activity in vivo. Unlike previous analogues, DT-23 inhibits fungal growth (MIC50 = 15 μg/mL) and only 1.5 μg/mL synergizes with Amphotericin B to kill Cn in vitro. DT-23/Amphotericin B is also more protective against Cn infection in an insect model compared to each drug alone. Transcription profiling shows that DT-23 impacts early stages in IP synthesis and cellular functions impacted by IPK gene deletion, consistent with its targeted effect. This study establishes the first pharmacological link between inhibiting IPK activity and antifungal activity, providing tools for studying IPK function and a foundation to potentially develop a new class of antifungal drug.

Keywords: Cryptococcus neoformans; IP3K; IP6K; antifungal drug; inositol polyphosphate kinase; purine analogue.

MeSH terms

  • Amphotericin B / pharmacology
  • Animals
  • Antifungal Agents* / chemical synthesis
  • Antifungal Agents* / chemistry
  • Antifungal Agents* / pharmacology
  • Cryptococcosis / drug therapy
  • Cryptococcosis / microbiology
  • Cryptococcus neoformans* / drug effects
  • Cryptococcus neoformans* / enzymology
  • Cryptococcus neoformans* / genetics
  • Fungal Proteins / antagonists & inhibitors
  • Fungal Proteins / genetics
  • Fungal Proteins / metabolism
  • Microbial Sensitivity Tests
  • Phosphotransferases (Phosphate Group Acceptor)* / antagonists & inhibitors
  • Phosphotransferases (Phosphate Group Acceptor)* / genetics
  • Phosphotransferases (Phosphate Group Acceptor)* / metabolism
  • Purines* / chemical synthesis
  • Purines* / chemistry
  • Purines* / pharmacology

Substances

  • Antifungal Agents
  • Purines
  • Phosphotransferases (Phosphate Group Acceptor)
  • polyphosphate kinase
  • Fungal Proteins
  • Amphotericin B