Design of a phosphinate-based fluorescent probe for superoxide detection in mouse peritoneal macrophages.
3',6'-Bis(diphenylphosphinyl)fluorescein (PF-1) was synthesized as a highly selective and sensitive fluorescent probe for imaging O(2) (.-) in living cells. The design strategy for the probe was based on the nucleophilic mechanism of O(2) (.-) to mediate deprotection of this probe to give fluorescein. Upon reaction with O(2) (.-), the probe exhibits a strong fluorescence response and high selectivity for O(2) (.-) over other reactive oxygen species and some biological compounds. The phosphinate-based probe, as a new fluorescent reagent, is cell-permeable and can detect micromolar changes of O(2) (.-) concentrations by using confocal microscopy in living cells. The unique combination of good selectivity, high sensitivity, good water solubility, and rapid reactivity establishes the potential value of the probe for facilitating investigations of the generation, metabolism, and mechanisms of superoxide-mediated cellular homeostasis and injury.
Xu
Kehua
K
College of Chemistry, Chemical Engineering and Materials, Science, Shandong Normal University, Jinan 250014, China.
Liu
Xia
X
Tang
Bo
B
Yang
Guiwen
G
Yang
Yong
Y
An
Liguo
L
D000818:Animals; D002460:Cell Line; D005452:Fluoresceins / Q000138:chemical synthesis*; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D006706:Homeostasis / Q000502:physiology; D017737:Macrophages, Peritoneal / Q000473:pathology*; D051379:Mice; D010100:Oxygen / Q000032:analysis / Q000378:metabolism; D010721:Phosphinic Acids / Q000737:chemistry*; D017382:Reactive Oxygen Species / Q000032:analysis / Q000378:metabolism; D012680:Sensitivity and Specificity; D013050:Spectrometry, Fluorescence; D013481:Superoxides / Q000032:analysis* / Q000378:metabolism; D013997:Time Factors
C520074:3',6'-bis(diphenylphosphinyl)fluorescein; D005452:Fluoresceins; D005456:Fluorescent Dyes; D010721:Phosphinic Acids; D017382:Reactive Oxygen Species; D013481:Superoxides; D010100:Oxygen