A Novel Approach for Incorporation of Mono‐Functional Bioactive Phenols into Polyanhydrides

Abstract

Antiseptics based on phenol and phenolic derivatives were chemically incorporated into polyanhydrides as pendant groups via ester linkages. Polyanhydrides with antiseptic loadings of 46-58 wt.-% were obtained with molecular weights ranging from 9 400-23 000. In general, polymers with the bulkier antiseptics were more difficult to polymerize and yielded lower molecular weights. All polyanhydrides were amorphous with glass transition temperatures ranging from 27-58 °C. Polymers were deemed noncytotoxic after culturing L929 mouse fibroblast cells in media containing the polymers at two concentrations (0.10 and 0.01 mg · mL(-1) ) over three days. In summary, mono-functional bioactives can be chemically incorporated into noncytotoxic polyanhydrides.

Polyactives: controlled and sustained bioactive release via hydrolytic degradation

“…52 Thus, a phenol-containing small molecule precursor was initially synthesized (Figure 5A). 53 First, the ring opening of a cyclic dianhydride (e.g., pyromellitic anhydride, 8 ) was investigated, affording the phenol-containing dicarboxylic acid, or diacid ( 9 ). The diacid subsequently underwent solution polymerization using triphosgene as coupling agent to make the PAE ( 10 ); here, the phenols are linked to the backbone via ester bonds, whereas the repeat units are connected through anhydride bonds.…”

Antibacterial poly(ethylene terephthalate) surfaces obtained from thymyl methacrylate polymerization

“…Polyesters of alternating maleic anhydride/styrene or vinyl acetate copolymers with thymol (and eugenol, citronellol) were prepared by esterification reaction . More recently, phenolic derivatives as thymol were chemically incorporated into polyanhydrides as pendant groups via ester linkages . These polymers were hydrolytically degraded after 2 weeks releasing free phenolic antimicrobials in a controlled manner .…”

Biodegradable Polyesters Containing Ibuprofen and Naproxen As Pendant Groups

“…Drugs containing only one reactive functional group can be incorporated onto a polymer as pendant groups; we explored this type of chemical incorporation with phenolic antiseptics, achieving high drug loading (48-58 wt.%). 22 …”