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

Recent advances in optical bioimaging have prompted the need for minimal chemical reporters that can retain the molecular recognition properties and activity profiles of biomolecules. As a result, several methodologies to reduce the size of fluorescent and Raman labels to a few atoms (e.g., single aryl fluorophores, Raman active triple bonds and isotopes) and embed them into building blocks (e.g., amino acids, nucleobases, sugars) to construct native-like supramolecular structures have been described. The integration of small optical reporters into biomolecules has also led to smart molecular entities that were previously inaccessible in an expedite manner. In this article, we review recent chemical approaches to synthesize miniaturized optical tags as well as some of their multiple applications in biological imaging.

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Section: Fluorescent Amino Acids For Site-specific Peptide and Protei...mentioning

confidence: 99%

Miniaturized Chemical Tags for Optical Imaging

et al. 2022

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“…Marc Vendrell et al developed a new fluorescent amino acid, Phe-BODIPY, with excellent photophysical properties ( Figure 13 ). Subsequently, after identifying antifungal peptides with affinity for Candida cells, the team further synthesized fluorescent linear peptide 17 and used it for rapid detection of Candida in human urine samples [ 80 ]. Significantly, the minimal cell permeability and stability of antimicrobial peptides in biological environments limit their widespread use [ 81 ].…”

Section: Identification Of the Cell Wall Components Of Pathogenic Bac...mentioning

confidence: 99%

Recent Progress in Identifying Bacteria with Fluorescent Probes

Wang

et al. 2022

Molecules

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The development of new techniques to rapidly and accurately detect bacteria has drawn continuous attention due to the potential threats posed by bacteria to human health and safety. Recently, a novel strategy based on fluorescent probes has drawn considerable interest for the detection of bacteria due to its high selectivity, fast response, and simple operation. In this review, we summarize the recent progress on fluorescent probes for the specific recognition and discrimination of Gram-negative and Gram-positive bacteria. In particular, we outline current design strategies, such as targeting of the differences in surface components, cell wall components, endogenous enzymes, surface charge, and hydrophobicity of various kinds of bacteria to develop various fluorescent sensors (organic small-molecule fluorescent probes, nanoprobes, and metal ion probes). We also emphasize the application of organic molecules in probe recognition elements. We hope that this review can stimulate this research area in bacterial detection and imaging in the future.

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“…[43] Subsequent efforts have led to other Trp-based amino acids with 1) enhanced environmental sensitivity to monitor membrane fluidity in T cells [44] or 2) longer emission wavelengths, such as the red fluorescent Trp(redBODIPY), [45] which has been successfully adapted for solid-phase peptide synthesis. [46] Some of the latest examples in BODIPY amino acids have rendered smaller Phe-based compounds (Figure 4), which retain the fluorogenic character of Trp-BODIPY while reducing the overall size of the fluorophore, [47] and Cys-reactive activatable probes for the derivatization of small proteins. [48] Trp-based amino acids including smaller chemical modifications to boost their optical properties have been reported.…”

Section: Fluorescent Amino Acids For Site-specific Peptide and Protei...mentioning

confidence: 99%

Section: Fluorescent Amino Acids For Site-specific Peptide and Protei...mentioning

confidence: 99%

Miniaturized Chemical Tags for Optical Imaging

et al. 2022

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View full text Add to dashboard Cite

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

Abstract: Supporting information for this article is given via a link at the end of the document.

Cited by 27 publications

References 93 publications

Miniaturized Chemical Tags for Optical Imaging

Miniaturized Chemical Tags for Optical Imaging

Recent Progress in Identifying Bacteria with Fluorescent Probes

Miniaturized Chemical Tags for Optical Imaging

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