Date of Award

Fall 12-2011

Degree Type

Masters Thesis

Degree Name

Master of Science (MS)


Chemistry and Biochemistry


Mathematics and Natural Sciences

Committee Chair

Alvin A. Holder

Committee Chair Department

Chemistry and Biochemistry

Committee Member 2

Douglas S. Masterson

Committee Member 2 Department

Chemistry and Biochemistry

Committee Member 3

Wujian Miao

Committee Member 3 Department

Chemistry and Biochemistry


9-Anthraldehyde-N(4)-methylthiosemicarbazone (MeATSC), potassium (E)-2-(2-hydroxybenzylideneamino)-3-(1H-indol-3-yl)propanoate (K[(Sal-L-tryp)] and 2-(2-hydroxybenzylamino)-3-(1H-indol-3-yl)propanoic acid (the reduced Schiff base) were prepared using known synthetic procedures. Two novel thiosemicarbazone ligands, (E)-N-ethyl-2-(4-hydroxy-3-methoxybenzylidene)hydrazinecarbothioamide (N-Ethhymethohcarbthio) and (E)-N-ethyl-2-(1-(thiazol-2-yl)ethylidene)hydrazinecarbothioamide (acetylethTSC), were also prepared. All ligands were characterized by FT IR and electrochemistry. N-Ethhymethohcarbthio were characterized by elemental analysis whereas the reduced Schiff base and K[(Sal-L-tryp)] were characterized by ESI MS. X-ray crystallography was also used to characterize acetylethTSC. The ligands were then reacted with [VO(Sal-L-tryp)(H2O)] (1) (Sal-L-tryp = N-salicylidene-L-tryptophanate) to produce the novel complexes, [VO(Sal-L-tryp)(MeATSC)].1.5C2H5OH (2), [VO(Sal-L-tryp)(N-Ethhymethohcarbthio)].H2O (3), and [VO(Sal-L-tryp)(acetylethTSC)].0.75C2H5OH (4), respectively. All complexes were characterized by elemental analysis, ESI MS, IR, UV-visible, 1H and 13C NMR spectroscopy, and electrochemistry. Oxidized DMSO and DMSO-d6 solutions of each complex were also characterized by ESI MS and 1H NMR spectroscopy. [VO(Sal-L-tryp)(MeATSC)].1.5C2H5OH, [VO(Sal-L-tryp)(N-Ethhymethohcarbthio)].H2O, and [VO(Sal-L-tryp)(acetylethTSC)].0.75C2H5OH were observed to exhibit anti-proliferative activity against three colon cancer cell lines, HTC-116, Caco-2, and HT-29. When the anti-proliferative effects were compared with that of non-cancerous colonic myofibroblasts, less inhibition was observed. The results obtained suggest that these compounds can be used as potential chemotherapeutic agents.

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