Tunable bifunctional silyl ether cross-linkers for the design of acid-sensitive biomaterials

J Am Chem Soc. 2010 Dec 22;132(50):17928-32. doi: 10.1021/ja108568g. Epub 2010 Nov 24.


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 and the release rate of entrapped cargo and yield a material that is intrinsically nontoxic. In this work, we designed nontoxic 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 diseased cells. The implementation of silyl ether chemistry gave precise control over the rate of degradation and afforded devices that could degrade over the course of hours, days, weeks, or months, depending upon the steric bulk around the silicon atom. These novel materials could be useful for numerous biomedical applications, including drug delivery, tissue repair, and general surgery.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry
  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry*
  • Cross-Linking Reagents
  • Drug Delivery Systems
  • Drug Design
  • Ethers / chemistry*
  • Hydrogen-Ion Concentration
  • Molecular Structure
  • Trimethylsilyl Compounds / chemistry*


  • Acids
  • Biocompatible Materials
  • Cross-Linking Reagents
  • Ethers
  • Trimethylsilyl Compounds