Bioactive (co)oligoesters with antioxidant properties – synthesis and structural characterization at the molecular level

Abstract

ABSTRACT:A contemporary synthetic route, starting from the bioactive compound via the corresponding glycidyl ester and β-substituted β-lactone to (homo)-and (co)oligoesters with a bioactive moiety covalently linked as pendent groups along an oligomer backbone, was reported.The bioactive compounds were selected from antioxidants used in cosmetics. Two models of bioactive (homo)-and (co)oligoesters were synthesized via anionic ring-opening (co)oligomerization of p-methoxybenzoyloxymethylpropiolactone (p-AA-CH 2 -PL) initiated by p-anisic acid sodium salt. An analytical protocol was developed for a detailed structural characterization at the molecular level of these bioactive (co)oligoesters. The molecular level structure of the obtained bioactive (homo)-and (co)oligoesters was established by electrospray ionization tandem mass spectrometry (ESI-MS/MS) supported by 1 H NMR analysis.Additionally, the results presented here are important for the analysis of designed biodegradable polymeric controlled-release systems of bioactive compounds with potential applications in cosmetology.1

The Synthesis and Structural Characterization of Graft Copolymers Composed of γ-PGA Backbone and Oligoesters Pendant Chains

“…Advanced molecular characterization of γ-PGA- graft -3HB cooligomers was performed using electrospray ionization multistage mass spectrometry (ESI-MS n ). The ESI-MS n technique has been successfully applied by some of us in the structural studies of co-oligomers [ 46 – 49 ].…”

Bioactive oligomers from natural polyhydroxyalkanoates and their synthetic analogues

“…Incorporation of bioactive compounds into the β-lactones structure may lead to homo-and co-oligoesters with a bioactive moiety covalently linked as pendent groups along an oligomer backbone. This synthetic strategy was applied by us for preparation of the PHA synthetic analogues with ibuprofen pendant groups [44], pesticide moieties [45] and recently antioxidants used in cosme tics [46]. The respective synthetic pathway, presented on Scheme I shows synthesis of bioactive co-oligoesters via copolymerization of BL with β-substituted β-lactones containing covalently bonded selected bioactive moieties [e.g., ibuprofen, (4-chloro-2-methylphenoxy)acetic acid, and anisic acid].…”

Biocompatible terpolyesters containing polyhydroxyalkanoate and sebacic acid structural segments – synthesis and characterization

“…Development of so ionization techniques in mass spectrometry facilitates solving the difficult questions regarding the molecular structure of copolymers. 14,[29][30][31][32][33] To obtain precise information on the structure of the resulting PHBHx oligodiols at the molecular level, electrospray mass spectrometry ESI-MS was used. This technique is very useful for the structural characterisation of partially degraded PHA biopolyesters, especially for characterization of the chemical structure of the end groups of analysed oligomers.…”