Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 180-194.DOI: 10.6023/cjoc202306016 Previous Articles     Next Articles



杨维清a, 葛宴兵a, 陈元元a, 刘萍a, 付海燕b, 马梦林a,b,*()   

  1. a 西华大学理学院 四川省不对称合成与手性技术重点实验室 成都 610039
    b 四川大学化学学院 教育部绿色化学重点实验室 成都 610064
  • 收稿日期:2023-06-19 修回日期:2023-09-04 发布日期:2023-09-21
  • 基金资助:
    国家自然科学基金(22072099); 教育部春晖计划基金(Z2016163)

Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine

Weiqing Yanga, Yanbing Gea, Yuanyuan Chena, Ping Liua, Haiyan Fub, Menglin Maa,b()   

  1. a Key Laboratory of Asymmetric Synthesis and Chiral Technology of Sichuan Province, School of Science, Xihua University, Chengdu 610039
    b Key Laboratory of Green Chemistry and Technology of Ministry of Education, Faculty of Chemistry, Sichuan University, Chengdu 610064
  • Received:2023-06-19 Revised:2023-09-04 Published:2023-09-21
  • Contact: *E-mail:
  • Supported by:
    National Natural Science Foundation of China(22072099); Chunhui Program of Ministry of Education(Z2016163)

Determination of sulfhydryl amino acid content is of great importance for disease research. Therefore, it is necessary to develop a fluorescent probe that can detect sulfhydryl amino acids. In this paper, sixty-one 1,8-naphthoyl derivatives were successfully synthesized. These performances of compounds were measured by UV-Vis spectra and fluorescence spectra (FL). Unlike the non-fluorescent nitro-substituted compounds N-methyl-4-nitro-1,8-napthalimide (4a)~N-(m-fluorophenyl)-4-nitro-1,8-napthalimide (4s), the amino-substituted compounds N-methyl-4-amino-1,8-napthalimide (5a)~N-(m-fluorophenyl)-4-amino-1,8-napthalimide (5s) have strong yellow fluorescence, and the maleic anhydride-sub- stituted compounds N-methyl-4-(1H-pyrrole-2,5-diketone-1-yl)-1,8-napthalimide (6a)~N-(m-fluorophenyl)-4-(1H-pyrrole- 2,5-diketone-1-yl)-1,8-napthalimide (6s) have weak blue fluorescence. Of the 61 probes, 7 probes have fluorescent OFF-ON effect on cysteine (Cys) solutions. It was found that these probes have the potential to detect cysteine. The specificity of the probe for cysteine detection was explored by adding 21 amino acids as distracters. The fluorescence intensity at different pH values were studied. The response time between the detection probe and cysteine, and the variation of the fluorescence intensity of the probe solution with amino acid concentration were also studied. The linear correlation coefficients reached above 0.95. The response time of the probe was tested by fluorescence time spectral scanning. Through the above experiments, it was found that the probe showed a better sensitivity and selectivity for cysteine. The ability of seven fluorescent probes to be used for intracellular cysteine detection was explored by Hela cell fluorescence imaging and screened out probes with potential for biological detection.

Key words: synthesis, fluorescence molecular probe, cysteine, 1,8-napthalimide derivatives, cell fluorescence imaging