We investigated the hydrolytic resistance and photorelease activity of these materials and found that their properties reflected the functionality of the photocleavable coumarin structure. We dispersed the photoresponsive biomaterial in aqueous solutions with various pH values and measured the luminescence of NanoLuc released from the solid phase material via hydrolysis (Figure ). Among our biomaterials, 7MB was the most susceptible to the hydrolysis. We observed a significantly slower protein release from 9MB using Si-Carb-photolinker compared to 8MB (Figure ). Next, we evaluated the hydrolytic release of the proteins in the presence of carboxylesterase. In this study, minimal release of NanoLuc from the solid phase material was observed when Si-Carb-photolinker 9 was utilized (Figure ). These results, which directly reflect the hydrolytic stability of the photolinkers, are consistent with the molecular functionality of coumarins (Figure , Supplementary Figure ). Similar outcomes were obtained for photolysis (Figure ). The biomaterial 9MB bearing Si-Carb-photolinker 9 efficiently released NanoLuc upon photoirradiation compared with 8MB bearing Carb-photolinker 8. Altogether, we demonstrated that the improvement in molecular functionality contributes to the creation of high-performance protein-release biomaterials.