Abstract

The monomers methacryloyl uridine and methacryloyl adenosine have been polymerised under copper-mediated living radical conditions using poly(ethylene glycol) (PEG) macroinitiators to give triblock and pentablock copolymers of reasonable dispersity. The triblocks were used as initiators for the successful synthesis of pentablock copolymers. The secondary structures of the triblock and pentablock copolymers have been investigated using circular dichroism (CD) spectroscopy. The adenosine copolymers are found to exhibit more ordered secondary structures in water in comparison to the uridine derived polymers. New supramolecular structure is observed by CD upon mixing adenosine and uridine triblock copolymers in water. The polymers obtained are of interest as potential drug delivery agents through interaction with small molecules and oligonucelotides.

Highlights

  • There have been numerous accounts of biologically active polymers including peptides [1], nucleotides [2] and oligosaccharides [3] being bound to, or synthesised on polymeric support [4,5]

  • We previously reported the copper-mediated living radical polymerisation ofprotected and methacryloyl uridine and methacryloyl adenosine (Fig. 1) in solution [34], and on a solid support [35]

  • It has been demonstrated that bromoisobutyroyl poly(ethylene glycol) (PEG) can act as an initiator for copper-mediated polymerisation of the multifunctional methacryloyl uridine and methacryloyl adenosine monomers possessing unprotected and silyl protected hydroxyl groups

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Summary

Introduction

There have been numerous accounts of biologically active polymers including peptides [1], nucleotides [2] and oligosaccharides [3] being bound to, or synthesised on polymeric support [4,5]. The conjugation of bio-relevant compounds to poly(ethylene glycol) (PEG; ‘PEGylation’) has attracted particular interest and found many applications [6], including enhancing circulatory lifetime and therapeutic potential [7]. Though much debated [8], PEG has remained one of the major polymer components for materials with biological applications [9,10,11,12]. This is mainly because of its advantageous properties, including solubility in both aqueous and organic solvents (except diethyl ether or isopropanol) [13], crystallinity of. It has been shown that PEG-poly(nucleoside) diblocks form supramolecular assemblies in aqueous solution based on interactions between complementary bases [16] and block copolymers containing adenine self-assemble in THF due to the hydrogen-bonding self-complementarity of the adenine units [17]

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