Hussain Sameer, Lv Fengting, Qi Ruilian, Senthilkumar Thangaraj, Zhao Hao, Chen Yanyan, Liu Libing, Wang Shu
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
College of Chemistry, University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
ACS Appl Bio Mater. 2020 Jan 21;3(1):20-28. doi: 10.1021/acsabm.9b00691. Epub 2019 Sep 6.
A water-soluble polyfluorene derivative PFBTM-NMe bearing mannose as well as quaternary ammonium groups on side chains is designed and synthesized via click chemistry and Suzuki cross-coupling polymerization. The conjugated glycopolymer PFBTM-NMe displayed excellent solubility in polar solvents with absolute photoluminescence quantum yield (Φ) of 4.1% and 13.4% in water and methanol, respectively. Owing to the low doping of benzothiadiazole (BT) moieties along the backbone, PFBTM-NMe exhibited weak interchain Förster resonance energy transfer (FRET) in water. After binding with Gram-negative bacteria, that possess net negative charge and bunch of mannose binding lectins FimH on the surface, PFBTM-NMe showed strong FRET and ratiometric response owing to interchain polymer aggregation. Interestingly, Gram-positive bacteria () and fungi () did not present similar substantial response due to the absence of lectin proteins and less net negative charge on the surface. Moreover, confocal microscopy indicates that bacteria undergo aggregation after binding with PFBTM-NMe within 2 min and could be proficiently discriminate from fungi even in a mixed condition via fluorescence imaging technique, which facilitate the potential of this method for realistic use. Hence, by simply balancing the synergistic effect of electrostatic and carbohydrate-protein interactions between polymer PFBTM-NMe and microbes, the selective recognition and imaging of bacteria over fungi could be achieved within a very short period of time without employing any complicated procedures.
通过点击化学和铃木交叉偶联聚合反应,设计并合成了一种侧链带有甘露糖和季铵基团的水溶性聚芴衍生物PFBTM-NMe。共轭糖聚合物PFBTM-NMe在极性溶剂中表现出优异的溶解性,在水和甲醇中的绝对光致发光量子产率(Φ)分别为4.1%和13.4%。由于主链上苯并噻二唑(BT)基团的低掺杂,PFBTM-NMe在水中表现出较弱的链间Förster共振能量转移(FRET)。与表面带有净负电荷和大量甘露糖结合凝集素FimH的革兰氏阴性菌结合后,PFBTM-NMe由于链间聚合物聚集而表现出强烈的FRET和比率响应。有趣的是,革兰氏阳性菌()和真菌()由于表面缺乏凝集素蛋白且净负电荷较少,没有呈现出类似的显著响应。此外,共聚焦显微镜表明,细菌在与PFBTM-NMe结合后2分钟内会发生聚集,并且即使在混合条件下也能通过荧光成像技术与真菌有效区分,这有利于该方法在实际应用中的潜力。因此,通过简单地平衡聚合物PFBTM-NMe与微生物之间静电和碳水化合物-蛋白质相互作用的协同效应,无需任何复杂程序,就能在极短时间内实现细菌对真菌的选择性识别和成像。