The Synthesis And Properties Of Fluorescent Probes Based On Rohdamine B And Naphthalimide

Fluorescence measurements have properties with high sensitivity,good selectivity,rapid performance,easily operation and well cell imaging.The method based on fluorescence has been widely involved in many areas,such as biology,chemistry,environmental sciences and medicinal.Rhodamine B and naphthalimide derivatives exhibit high fluorescence quantum yield,photostability,simple structure and low cost,etc.Therefore,In this paper,two novel fluorescent probes based on rhodamine B and naphthalimide derivatives were synthesized to determine ATP of mitochondria and H₂S of lysosome,repectively.Specific process as follows:Firstly,two novel fluorescent probes were designed and synthesized,characterized by TOF-MS,1H NMR and13 C NMR.Secondly,a fluorescent probe named Mito-Rh is firstly synthesized and used to recognize ATP in mitochondrion.In the probe,rhodamine,diethylenetriamine and triphenylphosphonium are selected as fluorophore,reaction site and mitochondrion targeting group,respectively.Probe Mito-Rh is colorless and non-fluorescent.In the presence of ATP,the ring of rhodamine was opened along with red fluoresence emission.Probe Mito-Rh shows high sensitivity to ATP with 81-fold fluorescence enhancement and the detection range?0.1-10 mM?can match the concentration level of ATP in mitochondrion.Moreover,Mito-Rh provides excellent selectivity toward ATP over other biological anions?ADP,AMP,GTP,CTP,UTP?owing to concurrent effect of dual recognition sites?hydrogen bond and ?-? stacking?.In particular,the probe can localize in mitochondrion specifically and demonstrates the utility in the real-time detection of mitochondrial ATP concentration changes.Finally,a fluorescent probe named Lyso-Nh is firstly synthesized and used to recognize H₂S in lysosome.In the probe,naphthalimide,nitro-benzoxadiazole and morpholine are selected as fluorophore,reaction site and lysosome targeting group,respectively.Due to the influence on PET of morpholine and quenching group,probe Lyso-Nh has no fluorescence.When pH is up to five,binding H₂S to probe Lyso-Nh induced leaving of recognition site and protonation of nitrogen atoms,which resulted strong naphthalimide emission at 536 nm.Probe Lyso-Nh shows high sensitivity toH₂S with 72-fold fluorescence enhancement and excellent selectivity toward H₂S over other analytes.Moreover,probe Lyso-Nh demonstrates the utility in detection of lysosomal H₂S concentration changes.