Biodegradable resins for photochemical 3D printing via vinyl ester and vinyl carbonate functionalized amino acid-phosphoramidates

[Display omitted] •Innovative amino acid phosphoramidate-based vinyl ester and vinyl carbonate monomers for photochemical 3D printing.•Tune hydrolysis rates with varied amino acid components, creating custom degradation profiles.•Bioabsorbable degradation products amino acids and phosphates.•Successfully demonstrate 3D printing on desktop DLP and high-resolution multiphotolithography platforms.•Osteogenic differentiation studies indicate potential for bone regeneration applications. Photochemical 3D printing is a rapidly advancing technology for the fabrication of intricate structures with adjustable mechanical properties, and is also finding increasing interest in biomaterial scaffolds and personalized medicine. Currently, mostly polyester and polycarbonate-based photopolymers are used, but these are limited in their scope of degradation, for example, often being too slow for applications like tissue scaffolds. Herein, we design and develop novel amino acid phosphoramidite-based vinyl ester and carbonate resins. Model studies demonstrate hydrolysis to the corresponding amino acid and phosphate, the rate of which can be tuned by varying the amino acid components. We then transfer this to the design of photopolymer resins with tailored degradation rate profiles, ranging from days to several months, under simulated physiological conditions. 3D printing capabilities are demonstrated using a desktop digital light processing (DLP) printer and multiphotolithography (MPL). Cytocompatibility, cell viability and osteogenic differentiation studies indicate the potential of these newly developed biodegradable scaffolds for bone regeneration applications. Overall, this research presents a promising approach to overcome existing limitations in biodegradable photopolymer materials for 3D printing in biomedical applications.