Abstract
AbstractPeptides with pan‐antimicrobial affinity were synthesized and decorated with environmentally sensitive fluorophores nitrobenzoxadiazole (green) and merocyanine (red). The labeling efficacies against a range of clinically relevant fungal and Gram‐negative and positive bacterial species (Candida albicans, Escherichia coli, and Staphylococcus aureus) were explored. The fluorogenic probes containing exclusively l or d‐amino acids showed rapid and efficient labeling of all microbial species, whereas probes with a mixture of l or d‐amino acids failed to label fungi or bacteria, highlighting the importance of the α‐helical peptide structure for interaction with the microbial cell membrane. Importantly, the nature of the dye allowed fluorescence detection/labeling without the need for a wash step, paving the way for direct application of the probes.
Highlights
Late-stage diagnosis or misdiagnosis and assumption of microorganism-based diseases results in enormous health problems, economic burden and social complications, while leading to overuse and misuse of antibiotics that drive antimicrobial resistance.[1]
595/630 nm) that only “turn-on” on/in hydrophobic microbial membranes (Figure 1). These probes were applied in the imaging of clinically relevant microorganisms including C. albicans, Escherichia coli (Gram-negative bacteria), and Staphylococcus aureus (Gram-positive bacteria), and their mechanism of action explored by investigating the effect of L and D amino acid residues on selectivity, with the synthesis of six analogues of P11-6
The ability of NBDL and NBD-D to label C. albicans was first investigated with optimization of the probe concentration (Figure S1)
Summary
Late-stage diagnosis or misdiagnosis and assumption of microorganism-based diseases results in enormous health problems, economic burden and social complications, while leading to overuse and misuse of antibiotics that drive antimicrobial resistance.[1]. (eg, polarity, hydrophobicity, or viscosity).[8] Examples of these dyes include nitrobenzoxadiazole (NBD) and merocyanine (MeroCy), which show weak fluorescence in an aqueous environment and produce a much stronger signal, for example, upon binding to a hydrophobic target. This reduces background fluorescence and eliminates the need for wash steps, which is important in diagnostic applications. This environment-based activation strategy makes them outstanding candidates for probes for optical imaging of microorganisms as cell membranes are hydrophobic. These probes were applied in the imaging of clinically relevant microorganisms including C. albicans (fungus), Escherichia coli (Gram-negative bacteria), and Staphylococcus aureus (Gram-positive bacteria), and their mechanism of action explored by investigating the effect of L and D amino acid residues on selectivity, with the synthesis of six analogues of P11-6
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