Design And Synthesis Of Three-input "AND" Logic Gate Fluorescent Probe Targeted To Endoplasmic Reticulum And Proportion Imaging Of Hypochlorite

In different life activities,the organisms will spontaneously generate the right amount of reactive oxygen species,such as neural transmission in the signal conversion,immune system control,normal cell growth,the synthesis of human life compounds and metabolism and other life activities,active oxygen has played a very important role.When the body is produced excess oxygen,the reactive oxygen species will cause damage to cells,and even apoptosis,as well as other body oxidative damage.Through the research shows that the human body reactive oxygen species(ROS)is the main factor that causes a variety of diseases.And hypochlorous acid is the most active oxygen content and strong oxidizing.Most of the hypochlorous acid in the body will be decomposed into hypochlorite(ClO-).Therefore,how to monitor the hypochlorite(ClO-)in cells,especially in living cells,has gradually become one of the most challenging topics in the field of organic chemistry and chemical biology.In recent years,fluorescent probe molecules are often used in chemical sensors and molecular logic gates.The molecular logic gate is an emerging science that implements the traditional integrated circuit function at the molecular scale.In the traditional sense,the logic operation of silicon(also known as Boolean operation)with silicon as material is realized by the change of voltage.The logic operation on the supramolecular chemistry is via the interaction between the object and subject,the corresponding spectrum signal change,and logical calculation in the process of input and output corresponding to one by one.The logic of the fluorescent probe is the use of chemical synthesis of fluorescent dyes as a fluorescent probe molecule,the use of fluorescent probe molecules in the functional group of a specific identification of a substance to achieve the detection of specific substances,generally have higher sensitivity,shorter response time and so on.We designed and synthesized the three-input "AND-type" logic gate fluorescence probe NPA-CN targeted to the endoplasmic reticulum.The probe molecule is 6-bromo-2-naphthol as a luminescent mass and skeleton,the introduction of N-ethyl amide bond in the molecular structure,and a strong electron-withdrawing group of malononitrile,constitute the fluorescent molecular logic NPA-CN.In the NPA-CN probe molecule,there is a "push-pull" electron system in the molecule due to the push electrons of the strong electron-withdrawing and amide bonds of the malononitrile.It was found that functional groups of malononitrile were oxidized to aldehydes when water,hypochlorite and OH-were all present in the environment,forming molecular NPA-CHO.The probe molecule NPA-CN also has high light stability,low cytotoxicity,and good selectivity.So the molecular probe can be successfully applied to live cell imaging and in vivo imaging.When the fluorescent molecule NPA-CN is used in biological imaging,the probe molecules undergo a significant spectral change in the presence of water,hypochlorite,and OH-in the cell by laser confocal microscopy.The fluorescence intensity of the long wavelength(583 nm)was weakened and the fluorescence intensity of the short wavelength(499 nm)was enhanced.However,the fluorescence at short wavelength(499 nm)and long wavelength(583 nm)did not change significantlywhen the three inputs were changed to single or double input,and were co-located with ER-Tracker Red cells Imaging contrast,NPA-CN imaging on the rough endoplasmic reticulum.At the same time in the live imaging,the probe molecules can be used for zebrafish imaging analysis.In this work,a series of logic gate molecular probe systems were constructed by introducing a new detection mechanism to realize the detection of hypochlorite by NPA-CN probe molecules.The probe molecules reported in this work provide a potential for monitoring endogenous hypochlorites in related diseases.