Tunable Bifunctional Silyl Ether Cross-Linkers for the Design of Acid-Sensitive Biomaterials

Responsive polymeric biomaterials can be triggered to degrade using localized environments found in vivo. A limited number of biomaterials provide precise control over the rate of degradation, the release rate of entrapped cargo, and yield a material that is intrinsically non-toxic. Here we design non-toxic acid-sensitive biomaterials based on silyl ether chemistry. A host of silyl ether cross-linkers were synthesized and molded into relevant medical devices including Trojan horse particles, sutures, and stents. The resulting devices were engineered to degrade under acidic conditions known to exist in tumor tissue, inflammatory tissue, and within diseased cells. The implementation of silyl ether chemistry gave precise control over the rate of degradation, and depending upon the steric bulk around the silicon atom, afforded devices that could degrade over the course of hours, days, weeks, or months. These novel materials could be useful for numerous biomedical applications including drug-delivery, tissue repair, and general surgery.