Degradation of poly(β‐amino ester) gels in alcohols through transesterification: Method to conjugate drugs to polymer matrices

Abstract

Poly(β amino ester) polymers have received growing attention in the literature, owing to their ease of synthesis, versatile co-monomer selection, and highly tunable degradation kinetics. As such, they have shown extensive potential in many biomedical applications as well. In this work, it is demonstrated for the first time that PβAE polymers containing primary and secondary amine groups can undergo degradation by primary alcohols via transesterification mechanism. While this work emphasizes an important aspect of solvent compatibility of these networks, it also represents an interesting, simple mechanism for post synthesis drug incorporation, with riboflavin conjugation being demonstrated as a model compound.

Structure-property relationships of novel phosphonate-functionalized networks and gels of poly(β-amino esters)

“…According to these results, we can say that networks degrade via hydrolysis of the multiple ester groups on the backbone into small molecule diols, bis(-amino acids) and poly(acrylic acid) kinetic chains as reported in the literature [22,25,56].…”

Tunable degradation of acetalated dextran microparticles enables controlled vaccine adjuvant and antigen delivery to modulate adaptive immune responses

“…Suarez et al’s research suggested the potential use of Ace-DEX MPs for controlled cargo delivery. Although other acid-labile carriers prepared from poly(β-amino) esters (PBAEs), poly(ortho esters) (POEs), or polyketals have also demonstrated some flexibility in degradation kinetics [35–37], it is achieved mostly by varying polymer composition, which may result in complex manufacturing procedure and increased risk of adverse side effects associated with combining multiple biomaterials for controlled delivery [38]. These vehicles are also associated with other concerns: PBAEs may lead to severe side effects for long-term treatment due to potential toxicity [39, 40]; POEs are only stable under basic conditions and hydrolyze quickly in both acidic and neutral environments [41]; and, polyketals are synthesized via complex reactions, resulting in high manufacturing cost and limited accessibility [42].…”

Investigation of tunable acetalated dextran microparticle platform to optimize M2e-based influenza vaccine efficacy

“…By controlling MP CAC or polymer molecular weight, degradation half-lives can range from hours to months. Despite some flexibility in degradation kinetics of delivery vehicles formulated using other acid-sensitive polymers, such as poly(β-amino) esters (PBAEs), poly(ortho esters) (POEs), or polyketals, modulating degradation half-lives is achieved mostly through less straightforward chemical modifications or using polymer blends [34–36].…”