Dissertation
Dissertation > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Elements in organic compounds > Cycle system Ⅰ group elements, organic compounds > Organometallic compounds of the copper group

Synthesis, Structures and Bioactivities of New Bicopper(Ⅱ) Complexes Bridged by Dissymmetrical N,N’-bis(substituent)oxamide

Author YuZuo
Tutor LiYanTuan
School Ocean University of China
Course Medicinal Chemistry
Keywords N,N’-bis(substituent)oxamide Bicopper(Ⅱ) Complexes Crystal Structure DNA Interaction
CLC O627.12
Type Master's thesis
Year 2011
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The study of the interactions of transition–metal complexes with DNA has been an active field of research. Interest in this field stems from attempts to gain some insight into the interaction model between DNA and the complexes, and obtain some information about drug design and tools of molecular biology. Six bicopper(Ⅱ) complexes bridged by different dissymmetrical N,N’-bis(substituent)oxamide were synthesized, and characterized by means of X-ray single crystal diffraction, elemental analysis, molar conductivity and IR. The interactions of the six complexes with DNA were also investigated by using UV absorption and fluorescence spectra, electrochemical techniques, and viscometry. Moreover, the cytotoxic activities of the six complexes were studied in vitro.This thesis consists of three sections as follows:1. Four kinds of dissymmetrical N,N’-bis(substituent)oxamide were synthesized and characterized. By controlling counter anions, pH values and solvents, six bicopper(Ⅱ) complexes, [Cu2(hmpo)(phen)](ClO4)·H2O (1)、[Cu2(hmpo)(bpy)]- (ClO4)·-H2O (2)、[Cu2(ebho)(phen)2](ClO4)·H2O (3)、[Cu2(dmapox)(Me2bpy)](Pic) (4)、[Cu2(dmpoda)(bpy)](pic)·H2O (5) and [Cu2(dmapox)(Me2bpy)](ClO4) (6), were obtained and characterized by elemental analyses, IR and electronic spectra and single-crystal X-ray diffraction.2. Interactions of the six bicopper(Ⅱ) complexes (1)6 with herring sperm DNA (HS-DNA) are investigated by using UV absorption and fluorescence spectra, electrochemical techniques, and viscometry. The results suggest that the six bicopper(Ⅱ) complexes interacts with DNA by intercalation with the intrinsic binding constants following the order of (1) > (3) > (2)、(5) > (4)、(6). The influence of structural variation of the terminal ligands and cis/trans conformation of oxamide in the bicopper(Ⅱ) complexes on DNA-binding properties is preliminarily discussed.3. The cytotoxicities of the complexes were tested by SRB methods. The results show that the six bicopper(Ⅱ) complexes (1)6 have the cytotoxic activities. The DNA-binding abilities of the six bicopper(Ⅱ) complexes are consistent with in vitro cytotoxic activities. and both follow the order (1) > (3) > (2)、(5) > (4)、(6). Complex (3) with the strongest DNA binding activities have the strongest effects on SMMC-7721 and A549 cell lines, with the IC50 = 3040 ng/mL.These results should be valuable in understanding the influence of different terminal ligands on the interaction between bicopper(Ⅱ) complexes and DNA, and enrich the experience for design and synthesis of inorganic therapeutic medicine with the chemotherapy ability of high activity and low toxicity.

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