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New Peptide Based Fluconazole Conjugates with Expanded Molecular Targets.

Wioletta Brankiewicz1, Joanna Okońska2, Katarzyna Serbakowska1

  • 1Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdańsk University of Technology, Narutowicza 11/12, 80-233 Gdańsk, Poland.

Pharmaceutics
|April 23, 2022
PubMed
Summary

New antifungal drug conjugates combining fluconazole (FLC) with peptides show potent activity against fluconazole-resistant Candida albicans. These novel agents target cell membranes with low human cell toxicity, offering promising alternatives for treating dangerous fungal infections.

Keywords:
Candidaantimicrobial peptidescell penetrating peptidesfluconazolepeptide-drug conjugatesresistance

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Area of Science:

  • Medicinal Chemistry
  • Mycology
  • Drug Discovery

Background:

  • * *Candida* spp. infections are commonly treated with azole antifungals, with fluconazole (FLC) being the most widely used clinical agent.
  • * Combined antifungal therapies show promise for treating severe systemic *Candida* infections.
  • * Development of novel antifungal agents is crucial due to rising resistance.

Purpose of the Study:

  • * To design, synthesize, and evaluate novel conjugates linking fluconazole (FLC) to cell-penetrating or antimicrobial peptides.
  • * To assess the biological activity of these conjugates against *Candida albicans*, including fluconazole-resistant strains.
  • * To investigate the mechanism of action and cytotoxicity of the most promising conjugates.

Main Methods:

  • * Synthesis of five FLC-peptide conjugates, varying in peptide sequence and linkage site.
  • * Antifungal activity testing against reference and clinical isolates of *C. albicans* using standard assays.
  • * Mechanism of action studies using fluorescence microscopy, scanning electron microscopy, and flow cytometry.
  • * Cytotoxicity assessment against human cells.

Main Results:

  • * Two conjugates, FLCpOH-TP10-NH2 and FLCpOH-TP10-7-NH2, demonstrated high activity against fluconazole-susceptible and resistant *C. albicans* strains.
  • * These conjugates exhibited enhanced fungicidal effects compared to fluconazole alone and targeted the cell membrane.
  • * The active conjugates displayed low cytotoxicity towards human cells, with IC90 values comparable to MIC50 values against *C. albicans*.
  • * Conjugation via the hydroxyl group of FLC was essential for activity; linkage via the triazole ring nitrogen resulted in inactive compounds.

Conclusions:

  • * Novel fluconazole-peptide conjugates, particularly FLCpOH-TP10-NH2 and FLCpOH-TP10-7-NH2, are effective against *C. albicans*, including resistant strains.
  • * These conjugates represent potential candidates for new antifungal therapies due to their potent activity, targeted mechanism, and favorable safety profile.
  • * The linkage strategy is critical for the antifungal efficacy of FLC-peptide conjugates.