Synthesis of a New Cyanoacrylate Monomer and Its Application in Fluorescence Imaging in vivo

A new cyanoacrylate monomer with fluorescein isothiocyanate (FITC) labeling was synthesized. It could copolymerize with any other cyanoacrylate monomers and result in copolymer being able to produce fluorescence. Well fluorescence imaging could be got when the copolymer was embedded in subcutaneous tissue of Sprague-Dawley (SD) mice. We also discussed the degradation pattern of polycyanoacrylate by monitoring the fluorescence intensity with time. The synthesis was started with anthracene /cyanoacrylate acid adduct and 6-(4,4'-dimethoxytriphenylmethyl)-amino-l-hexanol. After deprotection of 4,4'-dimethoxytriphenylmethyl group from intermediate anthracene/6-(4,4'-dimethoxytriphenylmethyl)-amino-1-hexanol cyanoacrylate adduct, FITC was labeled onto the amino group. The target product was finally got by reduction of the ethylenic bond. Structure of intermediates and target compound were identified by NMR and MS spectroscopy. Both the monomer and polymer could be observed fluorescence around 525 nm wavelength by an exciting light at 488 nm.