Abstract: To construct a polar ratio fluorescent probe for accurate detection of biological microenvironment, the probe IA based on naphthalene ring fluorophore was firstly synthesized by introducing malononitrile and N, N-dimethyl group on acenaphthene ketone, and then the polarity responsive ratio fluorescent probe IAN was synthesized by condensation reaction of IA amino group into heterocycle. The molecular structure and mass of probes IA and IAN were characterized by 1H NMR, 13C NMR and HRMS, and then the absorption and fluorescence spectra of probes IA and IAN in different polarity solvents were examined and compared by UV-Vis and fluorescence spectrophotometer. The results showed that IA exhibited single absorption and fluorescence emission peaks and fluorescence intensity of IA was gradually enhanced with solvent polarity increasing. Differently, double absorption and fluorescence emission peaks of IAN were simultaneously detected in solvents (λem=474 nm, and 552 nm), and the fluorescence intensity ratio I474 nm/I552 nm produced a sensitive Boltzmann function response to solvent polarity changes. Compared with IA, IAN was able to respond accurately to environmental polarity changes as a ratio fluorescent probe. The fluorescence intensity of the lesions was shown to be significantly lower than those of the healthy tissues by using IAN on mice with breast cancer and grouper hybrid Epinephelusfuscoguttatus♀×E.lanceolatus♂ with hepatobiliary syndrome. These findings indicated that amino group undergoing a condensation reaction to generate a heterocycle containing nitrogen atom increased the conjugation degree of lone pair electrons of the nitrogen atom to the π system, so that the probe IAN produced n→π* and π→π* molecular transition at the same time, and then enabled the construction of a ratio fluorescent probe responding sensitively to polarity changes.
李苗, 金潇仪, 姜硕, 孙萌, 田野. 用于生物微环境检测的极性比例荧光探针制备及性能分析[J]. 大连海洋大学学报, 2022, 37(4): 602-610.
LI Miao, JIN Xiaoyi, JIANG Shuo, SUN Meng, TIAN Ye. Preparation and properties of ratio fluorescent probe for polarity detecting of biological microenvironment. Journal of Dalian Ocean University, 2022, 37(4): 602-610.
2022, Vol. 37 
