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Fluorescent Probes Based On Coumarin And Quinoline

Posted on:2016-10-06Degree:MasterType:Thesis
Country:ChinaCandidate:X M WangFull Text:PDF
GTID:2191330461991767Subject:Organic Chemistry
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Fluorescent probes are effective tools for detecting small molecules and the metal ion concentration in vivo. Due to its high selectivity, easy synthesis, high sensitivity and low-price, therefore they have a wide range of biological applications prospects. They become a useful tool for Environmental Science and Life Science. It can be more effective in helping us to understand life from the microscopic point of view activities through the results of fluorescent chemical sensors and in vivo interaction parameters of the active substance. Two-photon microscopy (TPM) is a widely used tool in biomedical research. In contrast to the single-photon probes, the two-photon probes have a relatively low toxicity, good spatial orientation, and very effective in reducing auto-fluorescence of cells, but also can increase the organization’s ability to penetrate. Bisulfite (HSO3-) is the common preservatives in many food and beverage products. It has been discovered that certain concentration level causes asthmatic attacks and allergic reactions, such as difficulty in breathing, wheezing, hives, and gastrointestinal distress. Due to the reported harmful effects towards people, the threshold levels of bisulfite and sulfur dioxide in food and medicine have been rigorous controlled in many countries. Hypochlorite (ClO-), a reactive oxygen species, is a powerful antimicrobial agent that plays an important role in the immune system. But the abnormal production of hypochlorite would lead to some diseases including cardiovascular diseases, neuron degeneration, cancer, arthritis and so on. So it is an urgent problem which can detect hypochlorite and sodium bisulfite more quickly and effectively to be solved. We design and synthesis of coumarin and quinoline fluorescent chemical sensor which can selectively identify HC10 and HSO3-. The target probes were characterized by 1H NMR,13C NMR, IR and mass spectra. We also studied their optical properties and recognition mechanisms which could be successful used for cell imaging.1 We make specific modifications of coumarin, a larger conjugated system was linked to the 7 position of the coumarin which enables molecule good two-photon optical properties. In organic chemistry, aldehydes are known to react with bisulfite by forming an aldehyde-hydrogen sulfite adduct and this reaction is frequently employed to purify aldehydes. Herein we report a novel fluorescent probe (DMPCA). We have got the crystal structure of the probe DMCA which was successfully applied to the detection of bisulfite anion in HeLa cells.2 On the basis of our research group studies, we were certain quinoline modification. Compounds containing unbridged C=N bonds are usually non-fluorescent, where C=N isomerization is the predominant decay process of excited states. When the C=N bonds are decomposed by ClO" induced deoximation, the fluorescent will recover. Herein, we report a highly sensitive and selective fluorescent probe HQ for hypochlorite based on 6-substituted quinoline. Moreover, HQ has been successfully applied to monitor the endogenously produced hypochlorite in living cells (BV-2) stimulated by lipopolysaccharide (LPS).
Keywords/Search Tags:Coumarin, Quinoline, HSO3, HClO, two-photon, biological imaging
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