Design,Synthesis And Biomimetic Study Of Novel Fluoride And Formaldehyde Fluorescence Probes

Fluoride(F~?)as the smallest anion,has a special chemical properties.It is necessary for the human body one of the trace elements,the amount of fluoride ions for the prevention and treatment of dental caries and clinical treatment of osteoporosis have a good effect.While excess fluoride can cause mitochondrial function and immune system metabolic disorders.Therefore,the study of fluoride with high selectivity,stability,sensitivity and specific organelles targeting fluoride ion fluorescent probe,is conducive to a more in-depth understanding of the biological function of fluoride ions.Formaldehyde is both an important industrial raw material and a broadest carbonyl compound in the air.Formaldehyde will not only cause irritating chronic diseases,but also with the chloride in the air reaction to produce carcinogens,long-term exposure to not only the respiratory tract of the genetic damage,but also lead to human lymphocyte chromosome rupture.Therefore,the development of formaldehyde can be specific response,highly sensitive formaldehyde fluorescent probe,for the understanding and treatment of such diseases is of great significance.This work mainly covers the following two parts:A near-infrared fluorion fluorescence probe with mitochondrial targeting,was prepared froml,1,2-trimethyl-1H-benzo[e]indole,cyclohexanone,phosphorus oxychloride,4-chlorisorcinol,p-hydroxybenzaldehyde,Chloroborane and so on,and its structure was characterized by 1H NMR,13C NMR and MS.In the acetonitrile test system,when the probe solution was excited by 690nm UV light,the fluorescence is very weak.After incubation with F~?(TBAF)for 1.5 h,the solution emits strong fluorescence at the same excitation light,and its maximum emission wavelength is 745 nm,and its fluorescence intensity increases with the increase of fluoride concentration.The fluorescence response intensity of the probe was linearly correlated with the concentration of fluoride ion,the linear response range was 10-60?mol/L,and the detection limit was 8.15?mol/L.The results of interference and stability test showed that the probe had good selectivity to fluoride ion and the fluorescence response signal was stable between pH 6.8-8.0,which indicated that the probe was able to adapt to the environment of the organism.Laser confocal imaging experiments show that the probe can not only detect the fluoride ions in living cells also has good mitochondrial targeting.The three probe that reacts with formaldehyde were designed and synthesized by using 2,7-dihydroxynaphthalene,6-bromo-2-hydroxynaphthalene,2-naphthol,dimethylamine aqueous solution,phosphorus oxychloride,hydrazine hydrate and so on.And their structures were characterized by 1H NMR,13C NMR and MS.The fluorescence of the three probes was weak in the test system of PBS(10 mmol/L,pH=7.4)and under the excitation of 380 nm.After incubation with formaldehyde solution for about 1.3 hours,the TP-1 solution emits strong fluorescence and exhibits a new emission peak at the same excitation light.The maximum emission wavelength is 496 nm,and the TP-2 solution emits fluorescence and appears a new emission peak.The maximum emission wavelength of 523 nm,TP-3 solution can not emit fluorescence.The results of the interference test showed that TP-1 had better selectivity to formaldehyde than TP-2.Finally,we chose TP-1 as a fluorescent probe for the detection of formaldehyde.The stability test showed that TP-1 was stable at pH 6.8-8.0,indicating that TP-1 was able to adapt to the environment of organism.Laser confocal imaging experiments showed that the probe can not only detect formaldehyde,but also the detection of endogenous formaldehyde in living cells.