Issue 79, 2014

Novel thermosensitive telechelic PEGs with antioxidant activity: synthesis, molecular properties and conformational behaviour

Abstract

We report on the synthesis and solution properties of novel tailor-made polymer conjugates, which are highly compelling for biomedical applications due to their antioxidant activity and the potential to fine-tune their thermosensitive properties. These conjugates consist of polyethylene glycol (PEG) polymers containing antioxidant moieties, namely 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate or 2-benzamido-3-(3,5-di-tert-butyl-4-hydroxyphenyl)acrylate, as end groups that differ in activity and hydrophobicity. It was shown that all of the synthesized conjugates have low critical solution temperatures (LCSTs) characteristic of type II polymers on a phase diagram. By simply varying the PEG molecular weight, the solution properties, including the LCST value, could be easily tuned across a broad temperature range of 20–90 °C, providing an ideal method for the creation of thermosensitive polymers. It was also established that the LCST value and the polymer conjugate conformation depend on the antioxidant structure. From dynamic light scattering and small-angle X-ray scattering data, we were able to construct a complete sequence diagram of the conformational phase behaviour of the polymers with increasing temperature. It was observed that the conjugate conformation changes are the result of water shifting from a thermodynamically favourable solvent to an unfavourable one. This process then leads to compaction of the conjugate, followed by its aggregation.

Graphical abstract: Novel thermosensitive telechelic PEGs with antioxidant activity: synthesis, molecular properties and conformational behaviour

Supplementary files

Article information

Article type
Paper
Submitted
11 Jul 2014
Accepted
27 Aug 2014
First published
28 Aug 2014

RSC Adv., 2014,4, 41763-41771

Author version available

Novel thermosensitive telechelic PEGs with antioxidant activity: synthesis, molecular properties and conformational behaviour

O. Sergeeva, P. S. Vlasov, N. S. Domnina, A. Bogomolova, P. V. Konarev, D. I. Svergun, Z. Walterova, J. Horsky, P. Stepanek and S. K. Filippov, RSC Adv., 2014, 4, 41763 DOI: 10.1039/C4RA06978A

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