Date of Award
Fall 12-2011
Degree Type
Masters Thesis
Degree Name
Master of Science (MS)
Department
Chemistry and Biochemistry
School
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
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.
Copyright
2011, Nerissa Abigail Lewis
Recommended Citation
Lewis, Nerissa Abigail, "Chemical, Biological, and Preliminary In Vitro Studies of Novel Vanadium(IV) Complexes with Schiff Bases and Thiosemicarbazone Ligands" (2011). Master's Theses. 212.
https://aquila.usm.edu/masters_theses/212