Rational Design of Phe-BODIPY Amino Acids as Fluorogenic Building Blocks for Peptide-Based Detection of Urinary Tract Candida Infections

Mendive-Tapia, L, Mendive-Tapia, D, Zhao, C ORCID: https://orcid.org/0000-0002-0508-0236, Gordon, D, Benson, S, Bromley, MJ, Wang, W, Wu, J, Kopp, A, Ackermann, L and Vendrell, M ORCID: https://orcid.org/0000-0002-5392-9740 (2022) Rational Design of Phe-BODIPY Amino Acids as Fluorogenic Building Blocks for Peptide-Based Detection of Urinary Tract Candida Infections. Angewandte Chemie International Edition, 61 (17). e202117218. ISSN 1433-7851

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Abstract

Fungal infections caused by Candida species are among the most prevalent in hospitalized patients. However, current methods for the detection of Candida fungal cells in clinical samples rely on time-consuming assays that hamper rapid and reliable diagnosis. Herein, we describe the rational development of new Phe-BODIPY amino acids as small fluorogenic building blocks and their application to generate fluorescent antimicrobial peptides for rapid labelling of Candida cells in urine. We have used computational methods to analyse the fluorogenic behaviour of BODIPY-substituted aromatic amino acids and performed bioactivity and confocal microscopy experiments in different strains to confirm the utility and versatility of peptides incorporating Phe-BODIPYs. Finally, we have designed a simple and sensitive fluorescence-based assay for the detection of Candida albicans in human urine samples.