Department of Chemistry, Anhui Provincial Engineering Research Center for Polysaccharide Drugs, Wannan Medical college, Wuhu, 241002, P.R. China.
Org Biomol Chem. 2018 Mar 28;16(13):2264-2268. doi: 10.1039/c8ob00257f.
A two-photon active probe for physiological copper (Cu2+) detection is expected to play an important role in monitoring biological metabolism. Herein, a novel Schiff base derivative (E)-2,2'-((4-((4-(diethylamino)-2-hydroxybenzylidene)amino)phenyl)azanediyl)bis(ethan-1-ol) (L) with remarkable two-photon activity was developed and synthetically investigated. L presents high selectivity and sensitivity for Cu2+ sensing in ethanol/HEPES buffer (v/v, 1 : 1), which is accompanied by the fluorescence switching "off" and subsequently "on" with the addition of EDTA. The mechanism for the detection of Cu2+ is further analyzed using 1H NMR titration, mass spectra and theoretical calculations. Furthermore, since the probe L possesses good photophysical properties, excellent biocompatibility and low cytotoxicity, it is successfully applied to track Cu2+ in the cellular endoplasmic reticulum by two-photon fluorescence imaging, showing its potential value for practical applications in biological systems.
一种用于生理铜 (Cu2+) 检测的双光子活性探针有望在监测生物代谢中发挥重要作用。本文设计并合成了一种新型席夫碱衍生物 (E)-2,2'-((4-((4-(二乙氨基)-2-羟基苯亚甲基)氨基)苯基)偶氮)双(乙醇) (L)，其具有显著的双光子活性。L 在乙醇/HEPES 缓冲液 (v/v, 1:1) 中对 Cu2+ 传感表现出高选择性和灵敏度，伴随着荧光关闭，随后加入 EDTA 后又“打开”。通过 1H NMR 滴定、质谱和理论计算进一步分析了 Cu2+ 的检测机制。此外，由于探针 L 具有良好的光物理性质、优异的生物相容性和低细胞毒性，它成功地应用于通过双光子荧光成像来追踪细胞内质网中的 Cu2+，显示了其在生物系统中实际应用的潜在价值。
