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

Lauren Gwynne; George T. Williams; Kai‐cheng Yan; Jordan E. Gardiner; Kira L. F. Hilton; Bethany L. Patenall; Jennifer R. Hiscock; Jean‐yves Maillard; Xiao‐peng He; henan James; Adam C. Sedgwick; A. Toby A. Jenkins

doi:10.1002/ijch.202000105

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

Lauren Gwynne, George T. Williams, Kai‐cheng Yan, Jordan E. Gardiner, Kira L. F. Hilton, Bethany L. Patenall, Jennifer R. Hiscock, Jean‐yves Maillard, Xiao‐peng He, henan James, Adam C. Sedgwick, A. Toby A. Jenkins

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13 Citations (SciVal)

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.

Original language	English
Pages (from-to)	234-238
Number of pages	5
Journal	Israel Journal of Chemistry
Volume	61
Issue number	3-4
Early online date	10 Feb 2021
DOIs	https://doi.org/10.1002/ijch.202000105
Publication status	Published - 31 Mar 2021

Bibliographical note

Funding Information:
This work was supported in part by grant MR/N0137941/1 for the GW4 BIOMED DTP, awarded to the Universities of Bath, Bristol, Cardiff and Exeter from the Medical Research Council (MRC)/UKRI. The authors thank the National Natural Science Foundation of China (Nos. 21788102, 91853201, 21722801, 81673489 and 31871414), the Shanghai Municipal Science and Technology Major Project (No. 2018SHZDZX03), the International Cooperation Program of Shanghai Science and Technology Committee (No. 17520750100) and the Fundamental Research Funds for the Central Universities (222201717003) for financial support. LG and ATAJ would like to thank Dr Maisem Laabei for his help in acquiring strains for testing. GW would like to thank the GCDC at the University of Kent for funding. TDJ wishes to thank the Royal Society for a Wolfson Research Merit Award and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01). S. aureus

Publisher Copyright:
© 2021 The Authors. Israel Journal of Chemistry published by Wiley-VCH GmbH

Keywords

Bacterial detection
Chemosensors
Colorimetric sensors
Diagnostics
Wound infection

ASJC Scopus subject areas

General Chemistry

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Gwynne, L., Williams, G. T., Yan, K., Gardiner, J. E., Hilton, K. L. F., Patenall, B. L., Hiscock, J. R., Maillard, J., He, X., James, H., Sedgwick, A. C., & Jenkins, A. T. A. (2021). The Evaluation of Ester Functionalised TCF‐based Fluorescent Probes for the Detection of Bacterial Species. Israel Journal of Chemistry, 61(3-4), 234-238. https://doi.org/10.1002/ijch.202000105

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title = "The Evaluation of Ester Functionalised TCF‐based Fluorescent Probes for the Detection of Bacterial Species",

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.",

keywords = "Bacterial detection, Chemosensors, Colorimetric sensors, Diagnostics, Wound infection",

author = "Lauren Gwynne and Williams, {George T.} and Kai‐cheng Yan and Gardiner, {Jordan E.} and Hilton, {Kira L. F.} and Patenall, {Bethany L.} and Hiscock, {Jennifer R.} and Jean‐yves Maillard and Xiao‐peng He and henan James and Sedgwick, {Adam C.} and Jenkins, {A. Toby A.}",

note = "Funding Information: This work was supported in part by grant MR/N0137941/1 for the GW4 BIOMED DTP, awarded to the Universities of Bath, Bristol, Cardiff and Exeter from the Medical Research Council (MRC)/UKRI. The authors thank the National Natural Science Foundation of China (Nos. 21788102, 91853201, 21722801, 81673489 and 31871414), the Shanghai Municipal Science and Technology Major Project (No. 2018SHZDZX03), the International Cooperation Program of Shanghai Science and Technology Committee (No. 17520750100) and the Fundamental Research Funds for the Central Universities (222201717003) for financial support. LG and ATAJ would like to thank Dr Maisem Laabei for his help in acquiring strains for testing. GW would like to thank the GCDC at the University of Kent for funding. TDJ wishes to thank the Royal Society for a Wolfson Research Merit Award and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01). S. aureus Publisher Copyright: {\textcopyright} 2021 The Authors. Israel Journal of Chemistry published by Wiley-VCH GmbH",

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AU - Williams, George T.

AU - Yan, Kai‐cheng

AU - Gardiner, Jordan E.

AU - Hilton, Kira L. F.

AU - Patenall, Bethany L.

AU - Hiscock, Jennifer R.

AU - Maillard, Jean‐yves

AU - He, Xiao‐peng

AU - James, henan

AU - Sedgwick, Adam C.

AU - Jenkins, A. Toby A.

N1 - Funding Information: This work was supported in part by grant MR/N0137941/1 for the GW4 BIOMED DTP, awarded to the Universities of Bath, Bristol, Cardiff and Exeter from the Medical Research Council (MRC)/UKRI. The authors thank the National Natural Science Foundation of China (Nos. 21788102, 91853201, 21722801, 81673489 and 31871414), the Shanghai Municipal Science and Technology Major Project (No. 2018SHZDZX03), the International Cooperation Program of Shanghai Science and Technology Committee (No. 17520750100) and the Fundamental Research Funds for the Central Universities (222201717003) for financial support. LG and ATAJ would like to thank Dr Maisem Laabei for his help in acquiring strains for testing. GW would like to thank the GCDC at the University of Kent for funding. TDJ wishes to thank the Royal Society for a Wolfson Research Merit Award and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01). S. aureus Publisher Copyright: © 2021 The Authors. Israel Journal of Chemistry published by Wiley-VCH GmbH

PY - 2021/3/31

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N2 - 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.

AB - 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.

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KW - Chemosensors

KW - Colorimetric sensors

KW - Diagnostics

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IS - 3-4

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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