Date of Award

Fall 12-2011

Degree Type

Masters Thesis

Degree Name

Master of Science (MS)

Department

Chemistry and Biochemistry

Committee Chair

Dr. Alvin A. Holder

Committee Chair Department

Chemistry and Biochemistry

Committee Member 2

Dr. Douglas S. Masterson

Committee Member 2 Department

Chemistry and Biochemistry

Committee Member 3

Dr. Wujian Miao

Committee Member 3 Department

Chemistry and Biochemistry

Abstract

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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