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Design And Application Of Fluorescent Probe For Copper Ion Based On Rhodamine B

Posted on:2015-12-14Degree:MasterType:Thesis
Country:ChinaCandidate:B J QiFull Text:PDF
GTID:2181330431996852Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Recently, fluorescent probe technique is developing very rapidly, drawing more andmore attentions of scientific researchers for its high selectivity, high sensitivity, simpleoperation, less damage to cells, inexpensive equipment, etc. Rhodamine fluorescent dye hasbecome a star in the field of fluorescent probe technique because of its good photochemicaland photophysical properties.Copper is an important essential metal element in life organism. However, copperoverload in humans exhibits toxicity in that it causes various neurodegenerative diseases.Therefore, it is very important to develop a simple, rapid and sensitive method for detectingtrace amounts of copper ion in life science. In this dissertation, based on Schiff base reaction,two new rhodamine B lactam derivatives RH-P and RH-V were successfully designed andsynthesized. The specific contents are as follows:1. A novel rhodamine derivative RH-P was prepared by its precursor molecule rhodamineB lactam and3,4-dihydroxybenzaldehyde based on Schiff base reaction, and characterized bymeans of NMR. Fluorescence and UV-vis test indicated that it could be used for the detectionof Cu2+in aqueous solution with high sensitivity and selectivity. The detection limit of probeRH-P for Cu2+was determined to be about0.8μM. The mechanism of Cu2+recognition byprobe RH-P was proposed and confirmed by fluorescent analysis and DFT calculation. Thecytotoxicity of probe RH-P was evaluated using MTT assay in human breast cancer cell lineMCF-7, and the results showed that fluorescent probe RH-P has good water solubility,membrane permeability and biocompatibility owing to its catechol group. Fluorescencedetection and imaging experiment displayed that probe RH-P has the potential for Cu2+detection in vivo.2. Another rhodamine derivative RH-V was also successfully prepared by the samemethod as RH-P preparation, and characterized by means of NMR. We found that RH-V can be used as Cu2+enhanced fluorescent probe in aqueous solution with high sensitivity andselectivity for detection of Cu2+. The detection limit of RH-V for Cu2+was about0.82μM.The interaction of Cu2+and probe RH-V was invesgated by fluorescent analysis, and theresult indicated that the1:1stoichiometry is the most possible binding mode of RH-V andCu2+.Moreover, a comparison of fluorescence data for RH-P and RH-V revealed that thecatechol group of RH-P is essential for the recognition of Cu2+because RH-P exhibitedhigher sensitivity and selectivity than RH-V.
Keywords/Search Tags:Fluorescence probe, Cu2+, rhodamine B, catchol, bio-imaging
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