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Issue 4, 2016
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α-TOS-based RAFT block copolymers and their NPs for the treatment of cancer

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Abstract

α-Tocopheryl succinate (α-TOS) is a well-known mitochondrially targeted anticancer compound. However, a major factor limiting the use of α-TOS is its low solubility in physiological media. To overcome this problem, the aim of this work is the preparation of new polymeric and active α-TOS-based nanovehicle with a precise control over its macromolecular architecture. Reversible addition–fragmentation chain transfer polymerization (RAFT) is used to synthesize an α-TOS amphiphilic block copolymer with highly homogeneous molecular weight and relatively narrow dispersity. Macro-chain transfer agents (macro-CTA) based on poly(ethylene glycol) (PEG) of different molecular weights (MW, ranging from 4.6 to 20 kDa) are used to obtain block copolymers with different hydrophilic/hydrophobic ratios with PEG being the hydrophilic block and a methacrylic derivative of α-tocopheryl succinate (MTOS) being the monomer that formed the hydrophobic block. PEG-b-poly(MTOS) form spherical nanoparticles (NPs) by self-organized precipitation (SORP) or solvent exchange in aqueous media enabling to encapsulate and deliver hydrophobic molecules in their core. The resulting NPs are rapidly endocytosed by cancer cells. The biological activity of the synthesized NPs are found to depend on the MW of PEG, with the NP comprised of the higher MW copolymer resulting in a lower bioactivity due to PEG shielding, inhibiting cellular uptake by endocytosis. Moreover, the biological activity also depends on the MTOS content, as the biological activity increases as a function of MTOS concentration.

Graphical abstract: α-TOS-based RAFT block copolymers and their NPs for the treatment of cancer

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Publication details

The article was received on 12 Nov 2015, accepted on 25 Nov 2015 and first published on 27 Nov 2015


Article type: Paper
DOI: 10.1039/C5PY01811K
Citation: Polym. Chem., 2016,7, 838-850
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    α-TOS-based RAFT block copolymers and their NPs for the treatment of cancer

    R. Palao-Suay, M. R. Aguilar, F. J. Parra-Ruiz, S. Maji, R. Hoogenboom, N. A. Rohner, S. N. Thomas and J. San Román, Polym. Chem., 2016, 7, 838
    DOI: 10.1039/C5PY01811K

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