CHED 268 |
| Arylphosphonium salt-lipid conjugates have been shown to bind DNA, kill bacteria, inhibit acetylcholinesterase and are selectively taken up by malignant cell's mitochondria. Triarylphosphines were reacted with alpha-bromo-p-toluic acid in refluxing toluene to form salts. The product was added to thionyl chloride, and the reaction progress followed by IR. Quantitative conversions were routinely observed. Reaction with an alcohol or amine in excess or in a 1:1 molar ratio was done in the same container and the mixture stirred at room temperature overnight. The products are isolated by precipitation with diethyl ether and vacuum drying. The conjugates of urea and N-methylnitrosourea (MNU) were prepared by this method using DMF as the solvent. Vacuum distillation at 0.1-.5 torr removed excess DMF. Crude product was recrystalized from ethanol. IR, NMR, MP, HPLC, and MS verified formation of the desired products. MNU is a known DNA alkylator and arylphosphonium salts bind DNA. |
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Undergraduate Research Poster Session
2:30 PM-4:30 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Chemical Education |