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Design,Synthesis And Application Study Of Rhodamine Fluorescent Probes

Posted on:2016-03-16Degree:DoctorType:Dissertation
Country:ChinaCandidate:Q ZhouFull Text:PDF
GTID:1221330488969534Subject:Analytical Chemistry
Abstract/Summary:PDF Full Text Request
In recent years, the development of organic fluorescent molecular probe in the application of organisms have been important branch directions of analytical chemistry which is based on the specific recognition, and the chemical/biology sensing has attracted more and more attentions in the fields of biological, environmental, medical and so on. The simple operation and good reproducibility of fluorescence assay are widely applied to the detection of heavy metal ions. Rhodamine derivatives have been a special structure and optical properties, the spiro of rhodamine show colorless and non-fluorescence properties, and a specific object molecules can induce spiro-ring open which shows the color change and fluorescence properties. We have designed three kinds of new rhodamine derivatives fluorescent probes:rhodamine B-spiropyrane derivatives, rhodamine B-salicylic aldehyde derivatives and rhodamine-mercapto propionic aldehyde derivatives. These probes of rhodamine derivatives can complex with the object of specific molecular, and change chromophore or fluorescent molecular fluorescence properties. The targe molecules can be selectively detected by ultraviolet absorption spectra, fluorescence emission spectra and focusing microscope, and successful applied for detection of heavy metal ion in living cell and in zebfafish by fluorescence imaging.1.The fluorescent probe of based on rhodamine B-spiropyrane derivatives for detection Cu2+ and S2- in living cells by optical in vivo imaging. The previous research has shown that metal ions can induce spiro-ring of the rhodamine derivatives and spiropyrane derivatives opening. In this paper, we designed a novel fluorescent probe which combined rhodamine B hydrazide and aldehyde spiropyrane. The spiro of assembly fluorescent probe can be ring-opening by copperions inducing rhodamine and spiropyrane, and the probe can show fluorescent signal. The research results showed that the probe has a highly selectivity toward Cu+, then presence of S2- can quench the fluorescence of probe, therefore the probe can realize Cu2+ and S2-reversible, at the same time, the well cell compatibility of the probe can be applied for the detection of Cu2+ and S2- in living cells.2.The fluorescent probe of based on rhodamine B-salicylic aldehyde derivative for detection Cu+ in living cells and living organisms by optical in vivo and in vitro imaging. In this paper, we have designed and synthesized a fluorescent probe as a recognition site of Cu2+ by combination of rhodamine B and salicylaldehyde derivative, which can realize Cu2+ by the fluorescence spectrum and have a high selectivity for Cu2+ in cells. The research result showed that Cu2+ ions can induce the double-spiro-ring of the rhodamine derivatives opening and make its restore strongly fluorescence. Job’s plot calculation was employed to determine the binding of the probe and Cu+, and the result showed that it was 1:2 combination mode. We further research imaging of the probe in living cells and living tissue (zebrafish), which showed that the probe has a good biocompatibility and can detect Cu2+ in vivo and in vitro.3.The fluorescent probe of based on rhodamine B-sulfhydryl ether propionaldehyde for detecting Hg2+ in living cells and living organisms by optical in vivo and in vitro imaging. Due to the sulfur atom have strong affinity for Hg2+, we synthesized a high selective fluorescence probe toward Hg2+ based on rhodamine B-sulfhydryl ether propionaldehyde. The experimental results showed that the probe can be the selective recognition of Hg2+ by implemented for ultraviolet absorption spectrum and naked eye color change in certain solution. In addition, the fluorescence spectra and fluorescence color changes can be the recognition of Hg2+ also. Job’s plot calculation was employed to determine the binding of the probe and Hg 2+, and the result showed that it was 1:1 combination mode, and the detection limit of Hg+ in aqueous solution can reach to 1.6*10-8 M. The probe can detect Hg 2+ in living cells and living tissue (zebrafish). Furthermore, the influence of the levels of Hg2+ on health, aging, and disease may be illuminated in the upcoming future by utilizing such a fluorescence microscopic images approach. Thus, this method has a potential application value.
Keywords/Search Tags:Molecular probe of fluorescent, rhodamine B, in vivo, in vitro, Copperions, Mercuryion, sulfurions
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