Two-Photon-Absorption Triggered Release of 5-Fluorouracil from Isomer-Pure Polymer Bound Syn-Head-to-Head Dimers for Novel Intraocular Lenses

Annegret P. Busch, Norbert A. Hampp


Different stereoisomers of the cytotoxic 5-fluorouracil (5FU) homodimers were synthesized by photochemical [2+2]-cycloaddition and polymerized into MMA/HEMA to form a novel drug-loaded copolymer for intraocular lenses as irradiation-activated treatment for secondary cataract. Three isomers were obtained, and showed significant differences in cleavage efficiency on photo-cleavage via single-photon-absorption (SPA) and two-photon-absorption (TPA). The most efficient TPA cleavage rate was observed for the syn-head-to-head 5FU dimer, which was, consequently, used for drug loading of the polymeric material to obtain a drug-loaded material of higher efficiency compared to previous works. The light and thermal stability of the polymer were confirmed and multi-dose release of the drug in aqueous solution for possible repeated treatment of cataract was proven.


Photo-triggered drug release, 5-fluorouracil, isomers, two-photon-absorption, [2+2] cycloreversion, acrylic polymer

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