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

Raquel Palao-Suay, María Rosa Aguilar, Francisco J Parra-Ruiz, Samarendra Maji, Richard Hoogenboom UGent, NA Rohner, Susan N Thomas and Julio San Román (2016) POLYMER CHEMISTRY. 7(4). p.838-850
abstract
alpha-Tocopheryl succinate (alpha-TOS) is a well-known mitochondrially targeted anticancer compound. However, a major factor limiting the use of alpha-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 alpha-TOS-based nanovehicle with a precise control over its macromolecular architecture. Reversible addition-fragmentation chain transfer polymerization (RAFT) is used to synthesize an alpha-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 alpha-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.
Please use this url to cite or link to this publication:
author
organization
alternative title
alpha-TOS-based RAFT block copolymers and their NPs for the treatment of cancer
year
type
journalArticle (original)
publication status
published
subject
keyword
VITAMIN-E ANALOGS, ORGANIZED PRECIPITATION SORP, ANTICANCER DRUG-DELIVERY, E TPGS NANOPARTICLES, BREAST-CANCER, COMPLEX-II, TARGETING MITOCHONDRIA, RADICAL POLYMERIZATION, TOCOPHERYL SUCCINATE, POLYETHYLENE-GLYCOL
journal title
POLYMER CHEMISTRY
Polym. Chem.
volume
7
issue
4
pages
838 - 850
Web of Science type
Article
Web of Science id
000368895700010
JCR category
POLYMER SCIENCE
JCR impact factor
5.375 (2016)
JCR rank
6/86 (2016)
JCR quartile
1 (2016)
ISSN
1759-9954
DOI
10.1039/c5py01811k
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
7253616
handle
http://hdl.handle.net/1854/LU-7253616
date created
2016-06-15 14:19:23
date last changed
2016-12-19 15:44:41
@article{7253616,
  abstract     = {alpha-Tocopheryl succinate (alpha-TOS) is a well-known mitochondrially targeted anticancer compound. However, a major factor limiting the use of alpha-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 alpha-TOS-based nanovehicle with a precise control over its macromolecular architecture. Reversible addition-fragmentation chain transfer polymerization (RAFT) is used to synthesize an alpha-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 alpha-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.},
  author       = {Palao-Suay, Raquel and Aguilar, Mar{\'i}a Rosa and Parra-Ruiz, Francisco J and Maji, Samarendra and Hoogenboom, Richard and Rohner, NA and Thomas, Susan N and San Rom{\'a}n, Julio},
  issn         = {1759-9954},
  journal      = {POLYMER CHEMISTRY},
  keyword      = {VITAMIN-E ANALOGS,ORGANIZED PRECIPITATION SORP,ANTICANCER DRUG-DELIVERY,E TPGS NANOPARTICLES,BREAST-CANCER,COMPLEX-II,TARGETING MITOCHONDRIA,RADICAL POLYMERIZATION,TOCOPHERYL SUCCINATE,POLYETHYLENE-GLYCOL},
  language     = {eng},
  number       = {4},
  pages        = {838--850},
  title        = {\ensuremath{\alpha}-TOS-based RAFT block copolymers and their NPs for the treatment of cancer},
  url          = {http://dx.doi.org/10.1039/c5py01811k},
  volume       = {7},
  year         = {2016},
}

Chicago
Palao-Suay, Raquel, María Rosa Aguilar, Francisco J Parra-Ruiz, Samarendra Maji, Richard Hoogenboom, NA Rohner, Susan N Thomas, and Julio San Román. 2016. “α-TOS-based RAFT Block Copolymers and Their NPs for the Treatment of Cancer.” Polymer Chemistry 7 (4): 838–850.
APA
Palao-Suay, R., Aguilar, M. R., Parra-Ruiz, F. J., Maji, S., Hoogenboom, R., Rohner, N., Thomas, S. N., et al. (2016). α-TOS-based RAFT block copolymers and their NPs for the treatment of cancer. POLYMER CHEMISTRY, 7(4), 838–850.
Vancouver
1.
Palao-Suay R, Aguilar MR, Parra-Ruiz FJ, Maji S, Hoogenboom R, Rohner N, et al. α-TOS-based RAFT block copolymers and their NPs for the treatment of cancer. POLYMER CHEMISTRY. 2016;7(4):838–50.
MLA
Palao-Suay, Raquel, María Rosa Aguilar, Francisco J Parra-Ruiz, et al. “α-TOS-based RAFT Block Copolymers and Their NPs for the Treatment of Cancer.” POLYMER CHEMISTRY 7.4 (2016): 838–850. Print.