The Evaluation of Ester Functionalised TCF-based Fluorescent Probes for the Detection of Bacterial Species
The Evaluation of Ester Functionalised TCF-based Fluorescent Probes for the Detection of Bacterial Species
复制标题
用于细菌物种检测的酯功能化 TCF™ 荧光探针的评估
DOI：
10.1002/ijch.202000105
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发表时间：
2021-02-10
影响因子：
3.2
通讯作者：
Jenkins, A. Toby A.
中科院分区：
文献类型：
--
作者：
Gwynne, Lauren;Williams, George T.;Jenkins, A. Toby A.
酯的官能团在化学生物学和药物化学领域中常见，用于设计细胞透过性的活性分子。基于酯的前药物/前传感器策略被用来掩蔽极性官能团(即羧酸)，并改善这些功能分子的整体细胞通透性。然而，它们作为反应单元用于传感应用，包括细菌检测，还没有得到充分的探索。在此，我们合成了两种基于TCF的荧光探针TCF-OAC和TCF-OBU。不出所料，TCF-OAC和TCF-OBU对猪肝酯酶(PLE)均表现出明显的荧光(分别为22倍和43倍)和显色响应(从黄色到紫色)，检出限分别为1.18mU/mL和0.45mU/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(金黄色葡萄球菌)和革兰氏阴性铜绿假单胞菌(铜绿假单胞菌)和大肠杆菌(大肠杆菌)的浮游悬浮液的能力。TCF-OAC和TCF-OBU对革兰氏阳性菌和革兰氏阴性菌的荧光反应不同。培养1h后，TCF-OAc对金黄色葡萄球菌表现出更高的敏感性，表现出显著的荧光“开启”反应(16倍)，而TCF-OBU对铜绿假单胞菌具有更高的选择性，荧光反应增加了22倍。这些结果证明了酯链长度对细菌种类选择性的影响。
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.