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

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 developme...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 61; no. 17; pp. e202117218 - n/a
Main Authors: Mendive‐Tapia, Lorena, Mendive‐Tapia, David, Zhao, Can, Gordon, Doireann, Benson, Sam, Bromley, Michael J., Wang, Wei, Wu, Jun, Kopp, Adelina, Ackermann, Lutz, Vendrell, Marc
Format: Journal Article
Language:English
Published: Germany Wiley Subscription Services, Inc 19.04.2022
John Wiley and Sons Inc
Edition:International ed. in English
Subjects:
Amino Acids
Antiinfectives and antibacterials
Antimicrobial peptides
Biological activity
BODIPY
Boron Compounds
Candida
Candidiasis - diagnosis
Computer applications
Confocal microscopy
Conical intersection
Excited state
Fluorescence
Fungi
Humans
Labeling
Peptides
Peptides - chemistry
Probes
TD-DFT
Urinary Tract
Conical intersection
BODIPY
Candida
Fluorescence
Probes
Amino Acids
Excited state
TD-DFT
ISSN:1433-7851, 1521-3773, 1521-3773
Online Access:Get full text
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Summary: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. The rational design and synthesis of the first fluorogenic Phe‐based BODIPY amino acids, and their application to produce peptide‐based agents for rapid and wash‐free labelling of fungal cells is described. This technology has been exploited to develop a sensitive and low‐cost fluorescence‐based assay for the detection of Candida albicans in human urine using simple benchtop spectrophotometers.
Bibliography:These authors contributed equally to this work.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202117218