A 1,8-naphthalimide based fluorescent probe for sensing tyrosinase in zebrafish

• Published in: Microchemical journal Vol. 173; p. 107007
• Main Authors: Cao, Jing, Gong, Jiajia, Fu, Nanyan
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.02.2022
• Subjects: 3-Hydroxy benzyloxy; Fluorescent probe; Naphthalimide; Tyrosinase sensing; Zebrafish bioimaging; LOD; 3-Hydroxy benzyloxy; Tyrosinase sensing; Naphthalimide; HRMS; RNS; L-DOPA; ROS; Fluorescent probe; ICT; Zebrafish bioimaging; Cys; GSH; PET
• ISSN: 0026-265X; 1095-9149
• DOI: 10.1016/j.microc.2021.107007

Herein, we designed the tyrosinase specific sensing probe NITYO with recognition unit, 3-hydroxy benzyloxy, that also regarded as an electron-rich group that quenches the naphthalimide core by PET effect. When tyrosinase exists and catalyzes the secondary oxidation of NITYO, the fluorescence emission goes red shift with “turn-on” signal. We hypothesized and confirmed these results through comprehensive analysis such as molecular orbital analysis, molecular docking and HRMS. To sum up, we achieve the tyrosinase detection by NITYO with highly sensitivity and selectivity. It can be used in food samples and in vivo bioimaging. Besides, NITYO performs surperb linear fitting and lower detection limit (0.33 U/mL) within the range of 10–400 U/mL. [Display omitted] •A 1,8-naphthalimide-based fluorescent probe NITYO has been synthesized.•The sensing unit 3-hydroxy benzyloxy was triggered by tyrosinase oxidation.•The probe exhibited high sensitivity for tyrosinase with a detection limit of 0.33 U/mL.•NITYO was applied to the tyrosinase detection in food samples and zebrafish bioimaging.•Some techniques like docking, DFT calculation, HRMS were used to explain mechanism. Herein, we designed the tyrosinase specific sensing probe NITYO with recognition unit, 3-hydroxy benzyloxy, that also regarded as an electron-rich group that quenches the naphthalimide core by PET effect. When tyrosinase exists and catalyzes the secondary oxidation of NITYO, the fluorescence emission goes red shift with “turn-on” signal. We hypothesized and confirmed these results through comprehensive analysis such as molecular orbital analysis, molecular docking and HRMS. To sum up, we achieve the tyrosinase detection by NITYO with highly sensitivity and selectivity. It can be used in food samples and in vivo bioimaging. Besides, NITYO performs superb linear fitting and lower detection limit (0.33 U/mL) within the range of 10–400 U/mL.