Abstract
Aliphatic polyesters are an important class of polymeric materials for biomedical applications due to their versatile and tunable chemistry, biocompatibility and biodegradability. A capability of direct bonding with biomedically significant molecules, provided by the presence of the reactive end functional groups (FGs), is highly desirable for prospective polymers. Among FGs, N-hydroxysuccinimidyl activated ester group (NHS) and maleimide fragment (MI) provide efficient covalent bonding with –NH– and –SH containing compounds. In our study, we found that NHS- and MI-derived acyl chlorides efficiently terminate living ring-opening polymerization of ε-caprolactone, L-lactide, ethyl ethylene phosphonate and ethyl ethylene phosphate, catalyzed by 2,6-di-tert-butyl-4-methylphenoxy magnesium complex, with a formation of NHS- and MI-functionalized polymers at a high yields. Reactivity of these polymers towards amine- and thiol-containing model substrates in organic and aqueous media was also studied.
Highlights
We report that “living” alkoxy Mg-BHT chain end can be efficiently terminated under mild reaction conditions by acyl chlorides 1–4 (Scheme 2c) with simultaneous insertion of N-hydroxysuccinimidyl activated ester group (NHS) and maleimide fragment (MI) fragments, suitable for eventual interactions with –NH– and –SH containing compounds
We proposed that the synthesis of high molecular weight (MW) functionalized polymers can be based on the use of the complexes of more active metal than Al
The results of the use of acyl chloride 4 were less successful for MI functionalization of poly(εCL), MI-terminated poly(L-LA) and poly(EtEP) were synthesized with almost quantitative yields
Summary
Tissue engineering and surgery the challenge is to step up implementation of the articles made from biocompatible and biodegradable polymers [1,2,3,4]. Would be highly desirable for prospective polymer-based articles [5,6,7,8,9,10,11,12,13]. Most of biomedically significant molecules contain –NH– or –SH fragments by which the chemical binding with polymer can be realized if the event that polymer contains reactive functional groups (FGs) [5,9,14]. Among FGs, N-hydroxysuccinimidyl activated ester group (NHS) and maleimide fragment (MI) were successfully applied for covalent bonding with –NH– and –SH containing compounds, respectively (Scheme 1a) [12,15,16,17,18,19,20,21,22,23,24,25]
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