Synthesis and Complexation of Functionalized Mixed Thia-Aza-Macrocyclic and Medium Sized Ligands
Six ligands of mixed thia-aza donor atoms 40, 90, 100, 107, 110 and 112 have been synthesized and characterized. The metal complexes of Copper 114, Rhodium 116, and Nickel 115 with 1,8-dithia-4,11-diazacyclotetradecane 40 have been made and crystal structures grown in appropriate solvents to give good crystals suitable for X-ray crystallographic analysis. Other molecules whose crystals have been made and analyzed by X-ray crystallography are the secondary amine 82, tosylated double ligand tertiary amine 91, the seven member ring ester 100 and the perchlorate salt of the double nine member ligand tertiary amine 110. All these crystals have their analysis data in the appendix D. The seventh ligand 113 has been adapted, and complexed with rhodium and its crystal structure 117 has been analyzed.
The curative activity of the rhodium complex 116 was tested against ovarian cancer cells Nutu-19 at 1.54 mM concentrations. The results showed that the cells became detached with extreme morphological changes and extreme internal vesicle formation causing the cells to die. Ovarian normal cells, tested at the same concentration, showed that the cells remain attached, with no morphological changes and only slightly vesicle formation. Table 4 in chapter 2 shows 87% of the cancer cells died while only 30% of the normal ovarian cells died. If the toxicity of this complex can be further controlled and minimized, it may be very useful in the treatment of cancer in the future.
The ligand 40 was functionalized through carboxylic acid derivatives to give rise to the new ligand 90. Also ligand 107 was functionalized in the same way to give the new ligand 110, while the liands 82 and 107 were successfully joined by a butane chain to form a new ligand 112. In an attempt to synthesize the carbon bridged functionalized fourteen membered ring, ligand 99, the functionalized seven membered ring molecule 100 was isolated instead.
School:The University of Akron
School Location:USA - Ohio
Source Type:Master's Thesis
Keywords:macrocycles and medium cycles as anticancer in research functionalized multidonor atoms macrocylic ligands
Date of Publication:06/09/2009