Visible-Light-Responsive Surface Molecularly Imprinted Polymer for Acyclovir through Chicken Skin Tissue

The phototoxicity of UV light limits the application of conventional azobenzene-based photoresponsive molecularly imprinted polymers in the biomedical field. This paper reports a tetra-ortho-methoxy-substituted azobenzene, N-(4-((4-amino-2,6-dimethoxyphenyl)diazenyl)-3,5-dimethoxyphenyl)methacrylamide (ADDDM), whose photoswitching is induced by all visible-light irradiation (440 nm for trans form to cis form and 630 nm for cis form to trans form) in N,N-dimethylformamide and tetrahydrofuran (1:9, v/v). Using ADDDM as the monomer, a visible-light-responsive surface molecularly imprinted polymer (VSMIP) on silica microspheres was fabricated for acyclovir (ACV). VSMIP showed a higher drug loading capacity, better specificity, faster drug release rate, and faster photoisomerization rate constant to ACV than the corresponding visible-light-responsive surface molecularly nonimprinted polymer (VSNIP). The selectivity of VSMIP to ACV and competing materials (ganciclovir and triacetylganciclovir) was examined by ultraviolet–visible spectroscopy, and the VSMIP showed excellent specificity of recognition toward ACV. The VSMIP can realize a visible-light-triggered (440/630 nm) release and uptake of ACV through chicken skin tissue (1 mm in thickness).