Design, Synthesis, Performance Research And Biological Application Of Organic Small Molecule Fluorescent Probes

Fluorescence technology has become a non-invasively technique for detecting analytes,observing cell morphology and structure,and understanding physiological processes.Organic small molecule fluorescent probes have become a critical part of fluorescence technology in the field of biosensing due to their controllability of synthesis,design flexibility,and easy to use.At the current stage of clinical diagnosis and treatment,imaging methods had become an important auxiliary information.This paper proposed a simple method of the synthesis of 4-hydroxy-1,8-naphthalimide fluorophore,and further optimized the fluorescent probe to increase the reaction rated with MAO-A.Secondly,we also designed and synthesized a fluorinated organic small molecule probe IR-780-F,which is used to target tumor tissue,enhance drug efficacy,in vivo near-infrared fluorescence imaging,and ¹⁹F nuclear magnetic imaging,to improve tumors in the diagnosis and treatment process.The specific work was as follows:?1?Design and synthesis of fluorescent probes based on 1,8-naphthalimide moiety to detection and imaging of monoamine oxidase A1,8-Naphthalimide dyes are widely used in the preparation of fluorescent probes,but the current preparation methods have many shortcomings,including cumbersome and time-consuming processes,high reaction temperature,and the need to use a large number of dangerous chemicals concentrated hydrogen iodide acid or concentrated hydrobromic acid,and the produced methyl iodide or bromomethane is highly toxic,so it is of great significance to develop a fast,economical and safe preparation method.In this paper,a synthetic method of 4-hydroxy-1,8-naphthalimide fluorophore was developed which used DMSO and NaOH as raw materials in one step reaction.And the main advantages of the developed method were the simplicity of operation and the low cost.MAO-A can play a crucial role in physiological processes,relating to mental disorders.Therefore,the detection of MAO-A is of great significance for its early diagnosis of various functions and diseases in the human body.In this paper,an optimized design of the fluorescent probe for detecting MAO-A was further developed through the length of the alkyl group of the nitrogen atom on the 1,8-naphthalimide fluorophore.Finally,the confocal laser microscope technology was successfully used to verify that the probe can be used for endogenous MAO-A detection and fluorescence imaging in living cells and zebrafish.?2?Design and synthesis of small organic fluorine molecule probe IR-780-F for targeting tumor tissue and bioimaging based on IR-780 dyeWe know that IR-780 has unique photophysical properties and high-sensitivity near-infrared fluorescence imaging signals,including non-invasive,high sensitivity and deep tissue penetration.It has broad application prospects in tumor imaging and targeted therapy.Fluorine atom can occupy an important position in the development of drugs and magnetic resonance imaging due to their high gyromagnetic ratio and high sensitivity.Here,we described a fluorine-containing organic small molecule probe IR-780-F based on IR-780 dye to target tumor tissue,image fluorescence,improve metabolic stability,increase drug efficacy,and image ¹⁹F nuclear magnetic.The probe has similar optical characteristics as IR-780 and the characteristics of fluorine atoms in the fields of medicine and imaging.Then,spectral properties and stability have been characterized by studying the effect of different solvents.And the near-infrared fluorescence imaging of the probe in vivo and in vitro,the effectiveness of the therapeutic and targeting on tumor were verified with our experimental results as well as data from cell experiments and mouse experiments.Finally,we are going to carry out a series of experiments to demonstrate the ¹⁹F MRI imaging properties of this probe and good feasibility of this regimen.