Design and Synthesis of Fast‐Degrading Poly(anhydride‐esters)

Abstract

Fast-degrading, salicylate-based poly(anhydride-esters) were designed to degrade and release the active component, salicylic acid (SA), within 1 week. The polymer degradation was enhanced by using shorter or oxygen-containing aliphatic chains. A copolymer of diglycolic acid was also made with a salicylate-based diacid for comparison of polymer properties, including SA release. Both methods resulted in polyanhydrides with molecular weights ranging from 14 500 to 27 800 Da and displayed glass transition temperatures near physiological conditions, namely 33-40°C. the homoand copolymers completely degraded within one week releasing the chemically incorporated SA.

PolyMorphine: An innovative biodegradable polymer drug for extended pain relief

“…[32–34] Drug release can be controlled by altering the chemical composition of the polymer (i.e., “linker” molecule or making copolymers). [26, 34–36] These PAEs are also advantageous because they can be formulated into different geometries depending on the intended administration route. For example, they can be formulated into microspheres for injectable administration.…”

Storage stability study of salicylate-based Poly(anhydride-esters)

“…[1–4] The properties of the freshly prepared polymer are as follows: M w : 16,600, PDI: 2.8, T g : 44 °C, T d : 285 °C. Prior to storage, polymer 1 was ground using a mortar and pestle to obtain particles that were 100–500 μm in diameter.…”

“…[1–4] These salicylic acid-based poly(anhydride-esters) are both biodegradable and biocompatible. [1–6] They hydrolytically degrade over time to release free salicylic acid and the acid form of their linkers via a surface eroding, controlled release mechanism.…”

Stability of a salicylate-based poly(anhydride-ester) to electron beam and gamma radiation

“…The physicochemical properties of such polyanhydrides have been investigated over the last decade [5–14]. The ability to formulate these polymers into different geometries such as powders [6], disks [5, 9, 15], fibers [7], microspheres [10, 16], etc. contributes to their wide scope of applications.…”

“…Yet, the PAEs degrade faster at temperatures above 25 °C [15] and in the presence of water (Scheme 1). Further, the PAEs are shown to be non-toxic in vitro [14] and in vivo [9, 16, 17] and, therefore, have great potential in various biomedical applications [6, 9, 13, 14, 17]. However, the polymer should meet the pharmacopeial and commercial requirement of sterility [18–21].…”