| Schiff base refers to a class of compounds with imine or imine group condensed by amine with aldehyde or ketone.Since the selectivity of the amine and aldehyde/ketone is flexible,Schiff base ligands with diverse structures were emerged.Schiff base compounds show potential anti-inflammatory,anti-bacterial and anti-tumor effects in the field of pharmaceutical chemistry.Combining Schiff base and metal coordination could significantly improve its antimicrobial and antiproliferative ability,which makes Schiff base receive more attention.In addition,the metal elements of zinc,aluminum are closely related to human life.Excessive or lack of intake may pose a risk to the health of the human body.Schiff base ligand can form a rigid plane and has a good optical potential Schiff base ligand due to unsaturated double bond,Therefore,real-time,rapid and efficient detection of metal ions can provide a basis for deep understanding of the physiological and biochemical reactions of metal elements in living organisms and the diagnosis and treatment of certain diseases.The molecular fluorescent probe has become the focus as a result of its high selectivity,strong sensitivity and easy operation.Obeject: Synthesize a series of Schiff base copper complexes as well as aluminum and zinc ion fluorescent probe compounds based on 2-hydroxyl-1-naphthalene formaldehyde.In this paper,four novel 2-hydroxy-1-naphthalene formaldehyde-like Schiff base copper complexes were designed and synthesized for further application.A series of fluorescent probe compounds were synthesized and their properties such as selectivity and sensitivity were explored,which are expected for further application in cell image.Methods: Based on related literatures,four novel copper complexes and the Schiff base probe molelcules with characteristic responses to zinc or aluminum ions were designed and synthesized.The structure of four copper complexes were determined by single crystal diffraction.The interaction between the four novel copper complexes and DNA was studyed by spectral experiments and viscosity.The effect of complexes for human serum albumin and tumor cells were also studyed.The fluorescence examination properities of the probes for aluminum ions or zinc ions were investigated by UV-Vis spectroscopy,fluorescence spectroscopy,infrared spectroscopy,1H-NMR and ESI-MS.Selectivity and sensitivity of the fiuorescent probes were evaluated.The geometries and electronic properties of both the ligand L~3 and the Zn(II)complex were studied by DFT calculation,through which prove a recognition mechanism based on excited-state intramolecular proton transfer(ESIPT).Result: Four novel mononuclear copper complexes were obtained by solvent evaporation.By introducing different auxiliary ligands,the difference of their chemical structure resulted in the difference interaction between the four complexes and DNA.In the experiment,four complexes and DNA were identified to bind with moderate binding intensity.The results showed that the four complexes could inhibit the growth of human hepatocellular carcinoma cell line Hep G-2,but the same conditions showed weak inhibitory effect on normal human hepatocytes(LO2),especially the complex 4 with non-steroidal anti-inflammatory Drug(NSAID)salicylic acid exhibits a strong activity.In the latter two parts of the dissertation,zinc and aluminum ion fluorescent probes L~2 ~ L~5 were synthesized,in which L~3 and L~5 were screened as representative as zinc and aluminum fluorescent probes.Conclusions: Four new mononuclear Cu2+ complexes were designed and synthesized based on 2-hydroxy-1-naphthalene formaldehyde.The interaction between the four complexes and DNA and tumor cells was studied.The results showed that the complex 1 was inserted into the model Interaction with DNA,complex 2-4 were completely inserted with DNA.In addition,the complex 4 was found to exhibit more pronounced antitumor activity,which provided the possibility of finding a novel tumor drug.At the same time,two Schiff base metal zinc and aluminum ion probe compounds have been synthesized and screened,which have the advantages of high selectivity,strong sensitivity and good anti-interference ability,which provided the possibility for further application in vivo environment. |
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