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Functionalization of small triazine dendrons with maleimides and hydrazines on the periphery and DOTA group at the core
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2016
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In this work, we functionalized small triazine dendrons with maleimides (maleimide dendrimer) and triazine substituted hydrazines (hydrazine dendrimer) for potential use as theranostics in the presence of DOTA group as the reporter domain that can host metals for diagnostic applications. The model maleimide dendrimer displays four maleimides on the periphery that can readily react with thiols in a variety of solvents. Reactions of maleimide dendrimer with oligopeptides that contain cysteine have been examined. We began the work of hydrazine dendrimer with the study of hydrolytic stability of triazine substituted hydrazones (triazinyl hydrazones) and acyl hydrazones. At pH 5 and 7, triazinyl hydrazones showed higher hydrolysis rates. However, at pH 4, an inversion was observed in hydrolytic stability with triazinyl hydrazones more stable towards hydrolysis in comparison to corresponding acyl hydrazones due to the protonation of the triazine moiety. The experimental data is consistent with computation prediction. Then the success of synthesis of hydrazine dendrimer offers a model platform for targeted delivery of drugs containing ketone or aldehyde group. Specifically, the conjugation of hydrazine dendrimer with water insoluble drug bruceantin has been examined and produced water soluble model theranostics.
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Chemistry and Biochemistry