TY - JOUR
T1 - The Evaluation of Ester Functionalised TCF‐based Fluorescent Probes for the Detection of Bacterial Species
AU - Gwynne, Lauren
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
Y1 - 2021/3/31
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.
KW - Bacterial detection
KW - Chemosensors
KW - Colorimetric sensors
KW - Diagnostics
KW - Wound infection
UR - http://www.scopus.com/inward/record.url?scp=85100788564&partnerID=8YFLogxK
U2 - 10.1002/ijch.202000105
DO - 10.1002/ijch.202000105
M3 - Article
VL - 61
SP - 234
EP - 238
JO - Israel Journal of Chemistry
JF - Israel Journal of Chemistry
SN - 0021-2148
IS - 3-4
ER -