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The Evaluation of Ester Functionalised TCF‐Based Fluorescent Probes for the Detection of Bacterial Species
Israel Journal of Chemistry ( IF 2.3 ) Pub Date : 2021-02-10 , DOI: 10.1002/ijch.202000105 Lauren Gwynne 1 , George T. Williams 1, 2 , Kai‐Cheng Yan 1, 3 , Jordan E. Gardiner 1 , Kira L. F. Hilton 2 , Bethany L. Patenall 1 , Jennifer R. Hiscock 2 , Jean‐Yves Maillard 4 , Xiao‐Peng He 3 , Tony D. James 1, 5 , Adam C. Sedgwick 6 , A. Toby A. Jenkins 1
Israel Journal of Chemistry ( IF 2.3 ) Pub Date : 2021-02-10 , DOI: 10.1002/ijch.202000105 Lauren Gwynne 1 , George T. Williams 1, 2 , Kai‐Cheng Yan 1, 3 , Jordan E. Gardiner 1 , Kira L. F. Hilton 2 , Bethany L. Patenall 1 , Jennifer R. Hiscock 2 , Jean‐Yves Maillard 4 , Xiao‐Peng He 3 , Tony D. James 1, 5 , Adam C. Sedgwick 6 , A. Toby A. Jenkins 1
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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.
中文翻译：
基于酯功能化TCF的荧光探针用于细菌种类检测的评估
酯官能团在设计用于细胞渗透性活性分子的化学生物学和药物化学领域很常见。基于酯的前药/前传感器策略可用于掩盖极性官能团（即羧酸）并改善这些功能分子的总体细胞通透性。但是，还没有充分研究它们作为包括细菌检测在内的传感应用中的反应单元的用途。本文中，我们合成了两种基于TCF的荧光探针TCF-OAc和TCF-OBu。如预期的那样，TCF-OAc和TCF-OBu证明对猪肝酯酶（PLE）有明显的荧光（分别为22倍和43倍）和比色响应（黄色至紫色），检出限分别为1.18 mU / mL和0.45 mU / mL。有了这些结果，评估了这些探针检测革兰氏阳性金黄色葡萄球菌（S. aureus）和革兰氏阴性铜绿假单胞菌（P. aeruginosa）和大肠杆菌（E. coli）的浮游悬浮液的能力。在TCF-OAc和TCF-OBu之间观察到革兰氏阳性和革兰氏阴性细菌的荧光反应不同。孵育1小时后，TCF‐OAc证明对金黄色葡萄球菌更敏感，显示出显着的荧光“开启”响应（16倍）；而，TCF-OBU是朝着更具选择性铜绿假单胞菌，与观察到的荧光响应的22倍的增加。这些结果证明了酯链长度对细菌种类的选择性的影响。
更新日期：2021-02-10
中文翻译：
基于酯功能化TCF的荧光探针用于细菌种类检测的评估
酯官能团在设计用于细胞渗透性活性分子的化学生物学和药物化学领域很常见。基于酯的前药/前传感器策略可用于掩盖极性官能团（即羧酸）并改善这些功能分子的总体细胞通透性。但是，还没有充分研究它们作为包括细菌检测在内的传感应用中的反应单元的用途。本文中，我们合成了两种基于TCF的荧光探针TCF-OAc和TCF-OBu。如预期的那样，TCF-OAc和TCF-OBu证明对猪肝酯酶（PLE）有明显的荧光（分别为22倍和43倍）和比色响应（黄色至紫色），检出限分别为1.18 mU / mL和0.45 mU / mL。有了这些结果，评估了这些探针检测革兰氏阳性金黄色葡萄球菌（S. aureus）和革兰氏阴性铜绿假单胞菌（P. aeruginosa）和大肠杆菌（E. coli）的浮游悬浮液的能力。在TCF-OAc和TCF-OBu之间观察到革兰氏阳性和革兰氏阴性细菌的荧光反应不同。孵育1小时后，TCF‐OAc证明对金黄色葡萄球菌更敏感，显示出显着的荧光“开启”响应（16倍）；而，TCF-OBU是朝着更具选择性铜绿假单胞菌，与观察到的荧光响应的22倍的增加。这些结果证明了酯链长度对细菌种类的选择性的影响。
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