We report the synthesis of gemini-type amphiphilic molecules that form stable assemblies in aqueous medium. The assembly property of molecule M2 in aqueous solution was first inferred from peak broadening observed in the proton NMR spectrum. This was supported by dynamic light scattering and transmission electron microscopy analysis. The assembly formed from M2 (M2<sub>agg</sub>) was used to solubilize the hydrophobic drugs curcumin and doxorubicin at physiological pH. M2<sub>agg</sub> was able to effectively solubilize curcumin as well as protect it from degradation under UV irradiation. Upon solubilization in M2<sub>agg</sub>, curcumin showed excellent cell permeability, and higher toxicity to cancer cells over normal cells, likely due to enhanced cellular uptake and increased stability. M2<sub>agg</sub> also showed pH-dependent release of doxorubicin, resulting in controlled toxicity on cancer cell lines, making it a promising candidate for the selective delivery of drugs to cancer cells.
Copper-catalyzed reaction of enynamines with sulfonylazides provides acyclic and cyclic amidines. Nucleophilic addition of the tethered amino group on the in situ generated ketenimine forms a six-membered cyclic zwitterionic intermediate which facilitates migration of the tethered amino group to the C-center giving the acyclic amidine. On the other hand, migration of a substituent on the amino group to C- and C-centers results in the formation of cyclic amidines. Computational studies were carried out to validate the mechanism which indicates that the product distribution of the process depends on the substitutions on the enynamine backbone.
We report the synthesis of gemini-type amphiphilic molecules that form stable assemblies in aqueous medium. The assembly property of molecule M2 in aqueous solution was first inferred from peak broadening observed in the proton NMR spectrum. This was supported by dynamic light scattering and transmission electron microscopy analysis. The assembly formed from M2 (M2<sub>agg</sub>) was used to solubilize the hydrophobic drugs curcumin and doxorubicin at physiological pH. M2<sub>agg</sub> was able to effectively solubilize curcumin as well as protect it from degradation under UV irradiation. Upon solubilization in M2<sub>agg</sub>, curcumin showed excellent cell permeability, and higher toxicity to cancer cells over normal cells, likely due to enhanced cellular uptake and increased stability. M2<sub>agg</sub> also showed pH-dependent release of doxorubicin, resulting in controlled toxicity on cancer cell lines, making it a promising candidate for the selective delivery of drugs to cancer cells.
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