Substituted 1,3,5-Triazaadamantanes: Biocompatible and Degradable Building Blocks

摘要

Degradable polymers are important constituents of environmentally benign products and are used in applications that range from tissue engineering to gene and drug delivery. Hydrolytically labile polymers, such as polyesters, are particularly useful because of the ubiquitous presence of water in the environment and in living organisms. However, polyesters produce acidic byproducts upon degradation, a limitation for a number of applications. Polyphosphazenes are promising alternatives, but there is a need for new monomers that degrade to form benign byproducts. Herein we report the synthesis and study of 1,3,5-triazaadamantane (TAA) as a water-soluble unit for controlled degradation and aldehyde release. Formed from the condensation of a tris(aminomethyl)methane unit and three aromatic aldehydes, the TAA unit hydrolyzes under physiological conditions reverting to its basic precursors. We demonstrate how the degradation rate of the TAA unit can be tuned witt substituents, and further synthesize a hydrophilic TAA-basec dendrimer that is capable of binding solvatochromic probes.