Chemical, Biological, and Preliminary In Vitro Studies of Novel Vanadium(IV) Complexes with Schiff Bases and Thiosemicarbazone Ligands

<p>9-Anthraldehyde-N(4)-methylthiosemicarbazone (MeATSC), potassium (E)-2-(2-hydroxybenzylideneamino)-3-(1H-indol-3-yl)propanoate (K[(Sal-<em>L</em>-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, <em>(E</em>)-<em>N</em>-ethyl-2-(4-hydroxy-3-methoxybenzylidene)hydrazinecarbothioamide (<em>N</em>-Ethhymethohcarbthio) and (<em>E</em>)-<em>N</em>-ethyl-2-(1-(thiazol-2-yl)ethylidene)hydrazinecarbothioamide (acetylethTSC), were also prepared. All ligands were characterized by FT IR and electrochemistry. <em>N</em>-Ethhymethohcarbthio were characterized by elemental analysis whereas the reduced Schiff base and K[(Sal-<em>L</em>-tryp)] were characterized by ESI MS. X-ray crystallography was also used to characterize acetylethTSC. The ligands were then reacted with [VO(Sal-<em>L</em>-tryp)(H2O)] <strong>(1) </strong>(Sal-<em>L</em>-tryp = <em>N</em>-salicylidene-<em>L</em>-tryptophanate) to produce the novel complexes, [VO(Sal-<em>L</em>-tryp)(MeATSC)].1.5C2H5OH <strong>(2)</strong>, [VO(Sal-<em>L</em>-tryp)(<em>N</em>-Ethhymethohcarbthio)].H2O <strong>(3)</strong>, and [VO(Sal-<em>L</em>-tryp)(acetylethTSC)].0.75C2H5OH <strong>(4)</strong>, 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-<em>L</em>-tryp)(MeATSC)].1.5C2H5OH, [VO(Sal-<em>L</em>-tryp)(<em>N</em>-Ethhymethohcarbthio)].H2O, and [VO(Sal-<em>L</em>-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.</p>

Name thesis:degree_name

Master of Science (MS)

Level thesis:degree_level

Masters Thesis

Discipline thesis:degree_discipline

Chemistry and Biochemistry

Year dc:date.available

2011

Author dc:creator

• Lewis, Nerissa Abigail

Contributors dc:contributor

• Alvin A. Holder
• Douglas S. Masterson
• Wujian Miao

• vitro studies
• novel vanadium (IV) complexes
• schiff bases
• thiosemicarbazone ligands
• Chemistry

Repository record dc:identifier

https://aquila.usm.edu/masters_theses/212

OAI identifier oai:identifier

oai:aquila.usm.edu:masters_theses-1236