Spacer-free BODIPY fluorogens in antimicrobial peptides for direct imaging of fungal infection in human tissue

Lorena Mendive-Tapia, Can Zhao, Ahsan R. Akram, Sara Preciado, Fernando Albericio, Martin Lee, Alan Serrels, Nicola Kielland, Nick D Read, Rodolfo Lavilla () and Marc Vendrell ()
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Lorena Mendive-Tapia: Institute for Research in Biomedicine, Barcelona Science Park
Can Zhao: Manchester Fungal Infection Group, Institute of Inflammation and Repair, University of Manchester
Ahsan R. Akram: MRC/UoE Centre for Inflammation Research, University of Edinburgh
Sara Preciado: Institute for Research in Biomedicine, Barcelona Science Park
Fernando Albericio: Institute for Research in Biomedicine, Barcelona Science Park
Martin Lee: Edinburgh Cancer Research Centre, University of Edinburgh
Alan Serrels: Edinburgh Cancer Research Centre, University of Edinburgh
Nicola Kielland: Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Barcelona Science Park
Nick D Read: Manchester Fungal Infection Group, Institute of Inflammation and Repair, University of Manchester
Rodolfo Lavilla: CIBER-BBN, Networking Centre for Bioengineering, Biomaterials and Nanomedicine
Marc Vendrell: MRC/UoE Centre for Inflammation Research, University of Edinburgh

Nature Communications, 2016, vol. 7, issue 1, 1-9

Abstract: Abstract Fluorescent antimicrobial peptides are promising structures for in situ, real-time imaging of fungal infection. Here we report a fluorogenic probe to image Aspergillus fumigatus directly in human pulmonary tissue. We have developed a fluorogenic Trp-BODIPY amino acid with a spacer-free C-C linkage between Trp and a BODIPY fluorogen, which shows remarkable fluorescence enhancement in hydrophobic microenvironments. The incorporation of our fluorogenic amino acid in short antimicrobial peptides does not impair their selectivity for fungal cells, and enables rapid and direct fungal imaging without any washing steps. We have optimized the stability of our probes in human samples to perform multi-photon imaging of A. fumigatus in ex vivo human tissue. The incorporation of our unique BODIPY fluorogen in biologically relevant peptides will accelerate the development of novel imaging probes with high sensitivity and specificity.

Date: 2016
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DOI: 10.1038/ncomms10940

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