Abstract

Ultrasound assisted the copper-catalyzed cross-coupling reaction to synthesis 1-(10-bromoanthracene-9-yl)-1H-imidazole-4,5-dicarboxylic acid (A-Im). The obtained product was employed to modify graphene oxide (GO) surface to produce GO-A-Im. The resulted hybrid was characterized with Scanning Electron Microscope (SEM/EDS); X-ray Diffraction spectroscopy (XRD); X-ray photoelectron spectroscopy (XPS); Fluorescence spectroscopy; Fourier transformed infrared spectroscopy (FT-IR), Brunauer–Emmett–Teller (BET), and UV–Vis absorption spectroscopy. The synthesized (A-Im) moiety that was used for functionalization of GO, display a cyan emission around (496 nm), however, the GO hybrid exhibited blue photoluminescence around (403 nm). It has been proposed that the chemical attachment of the A-Im moiety onto GO surface leads to a distortion in the bandgap of the GO and the blue shift of luminescence [93 nm] was observed. Indeed the cytotoxicity properties of the synthesized hybrid were measured. The IC50 value for the hybrid was 23 µg/ml. The model drug (DOX) was loaded up to 91% on the carrier, and the release profile indicated a pH-dependent discharge with more release in acidic pH. The GO-A-Im/DOX was injected to the 4T1 tumor (murine breast cancer) bearing BALB/c mice and after 10 days the tumor was disappeared.

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