A new fluorescent dendrimer was obtained by modifying the periphery of a PAMAM dendrimer from zero generation. The modification involves substitution at the C-4 position with 1,8-naphthalimide units containing N-methylpiperazine and the addition of Cu(II) ions forming the metallodendrimer [Cu2(D)(NO3)2]. The dendrimer ligand and metallodendrimer were subjected to UV-vis, fluorescence spectroscopy, FT-IR, NMR, and SEM investigations to define their precise structure. The photophysical characteristics of the yellow-green fluorescent dendrimer were studied in organic solvents of different polarity. Results show that polar solvents favour a photoinduced electron transfer (PET) process. Experiments on the effect of pH in an ethanol - water solution (1:4 v/v) revealed the fluorescence of the dendrimer to be more than seventeen times higher than that in an acidic medium. Electron paramagnetic resonance (EPR) studies were performed to characterize the complexing ability of the dendrimer towards Cu(II) by varying the [Cu(II)/dendrimer external sites] molar ratio in DMSO solution. The EPR results suggest that Cu(II) formed a Cu-N2O2 square-planar coordination with nitrogen sites (N-CH3 sites of 1,8-methylpiperazine, and amine and amide groups) at the dendrimer internal/external interface, and 2 solvent molecules. The Cu(II) complex was characterized by restricted mobility conditions. Copper (II) ions were distributed between the dendrimer interface and the external surface; saturation of the nitrogen sites at the interface occurred at a 1:2 M ratio between Cu(II) and methylpiperazine units. These results are useful in view of the use of this metallodendrimer as anticancer and antimicrobial drugs. The antimicrobial activity of dendrimer ligand and its Cu(II) complex was tested against several model strains bacteria and yeasts in agar, in liquid medium, and after their deposition onto a cotton fabric. The results showed good antibacterial effect of dendrimer ligand, which was enhanced by its Cu(II) complexation.
Synthesis and characterization of fluorescent PAMAM dendrimer modified with 1,8-naphthalimide units and its Cu(II) complex designed for specific biomedical application
Cangiotti, Michela;
2021
Abstract
A new fluorescent dendrimer was obtained by modifying the periphery of a PAMAM dendrimer from zero generation. The modification involves substitution at the C-4 position with 1,8-naphthalimide units containing N-methylpiperazine and the addition of Cu(II) ions forming the metallodendrimer [Cu2(D)(NO3)2]. The dendrimer ligand and metallodendrimer were subjected to UV-vis, fluorescence spectroscopy, FT-IR, NMR, and SEM investigations to define their precise structure. The photophysical characteristics of the yellow-green fluorescent dendrimer were studied in organic solvents of different polarity. Results show that polar solvents favour a photoinduced electron transfer (PET) process. Experiments on the effect of pH in an ethanol - water solution (1:4 v/v) revealed the fluorescence of the dendrimer to be more than seventeen times higher than that in an acidic medium. Electron paramagnetic resonance (EPR) studies were performed to characterize the complexing ability of the dendrimer towards Cu(II) by varying the [Cu(II)/dendrimer external sites] molar ratio in DMSO solution. The EPR results suggest that Cu(II) formed a Cu-N2O2 square-planar coordination with nitrogen sites (N-CH3 sites of 1,8-methylpiperazine, and amine and amide groups) at the dendrimer internal/external interface, and 2 solvent molecules. The Cu(II) complex was characterized by restricted mobility conditions. Copper (II) ions were distributed between the dendrimer interface and the external surface; saturation of the nitrogen sites at the interface occurred at a 1:2 M ratio between Cu(II) and methylpiperazine units. These results are useful in view of the use of this metallodendrimer as anticancer and antimicrobial drugs. The antimicrobial activity of dendrimer ligand and its Cu(II) complex was tested against several model strains bacteria and yeasts in agar, in liquid medium, and after their deposition onto a cotton fabric. The results showed good antibacterial effect of dendrimer ligand, which was enhanced by its Cu(II) complexation.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
