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The Evaluation of Ester Functionalised TCF‐based Fluorescent Probes for the Detection of Bacterial Species

Gwynne, Lauren, Williams, George T., Yan, Kai-Cheng, Gardiner, Jordan E., Hilton, Kira L.F., Patenall, Bethany L., Hiscock, Jennifer R., Maillard, Jean-Yves, He, Xiao-Peng, James, Tony D., and others. (2021) The Evaluation of Ester Functionalised TCF‐based Fluorescent Probes for the Detection of Bacterial Species. Israel Journal of Chemistry, . pp. 1-6. ISSN 0021-2148. E-ISSN 1869-5868. (doi:10.1002/ijch.202000105) (KAR id:86683)

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https://doi.org/10.1002/ijch.202000105

Abstract

The ester functionality is commonly seen in the areas of chemical biology and medicinal chemistry for the design of cell‐permeable active molecules. Ester‐based pro‐drug/pro‐sensor strategies are employed to mask polar functional groups (i. e. carboxylic acids) and improve the overall cell permeability of these functional molecules. However, their use as reactive units for sensing applications, including bacterial detection, has not been fully explored. Herein, we synthesised two TCF‐based fluorescent probes, TCF‐OAc and TCF‐OBu. As expected, both TCF‐OAc and TCF‐OBu demonstrated a significant fluorescence (22‐ and 43‐fold, respectively) and colorimetric response (yellow to purple) towards porcine liver esterase (PLE) with a limit of detection of 1.18 mU/mL and 0.45 mU/mL, respectively. With these results in hand, the ability of these probes to detect planktonic suspensions of gram‐positive Staphylococcus aureus (S. aureus) and gram‐negative Pseudomonas aeruginosa (P. aeruginosa), and Escherichia coli (E. coli) were evaluated. Different fluorescence responses for gram‐positive and gram‐negative bacteria were observed between TCF‐OAc and TCF‐OBu. After 1 h incubation, TCF‐OAc proved more sensitive towards S. aureus, demonstrating a significant fluorescence “turn on” response (16‐fold); whereas, TCF‐OBu was more selective towards P. aeruginosa, with a 22‐fold increase in the fluorescence response observed. These results demonstrate the influence of the ester chain length on the selectivity for bacterial species.

Item Type: Article
DOI/Identification number: 10.1002/ijch.202000105
Subjects: Q Science > QD Chemistry > QD431 Organic Chemistry- Biochemistry- Proteins, peptides, amino acids
Divisions: Divisions > Division of Natural Sciences > School of Physical Sciences
Depositing User: Jennifer Hiscock
Date Deposited: 19 Feb 2021 18:29 UTC
Last Modified: 22 Feb 2021 09:55 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/86683 (The current URI for this page, for reference purposes)
Hiscock, Jennifer R.: https://orcid.org/0000-0002-1406-8802
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