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Abstract: 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)
Template and target information: acyclovir, ACV
Author keywords: Acyclovir, azobenzene functional monomer, Drug delivery system, visible-light-responsive surface molecularly imprinted polymer