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Polymer-protein conjugation via a 'grafting to' approach: a comparative study of the performance of protein-reactive RAFT chain transfer agents

Nane Vanparijs (UGent) , Samarendra Maji (UGent) , Benoit Louage (UGent) , Lenny Voorhaar (UGent) , Duchan Laplace (UGent) , Qilu Zhang (UGent) , Y Shi, Wim E Hennink, Richard Hoogenboom (UGent) and Bruno De Geest (UGent)
(2015) POLYMER CHEMISTRY. 6(31). p.5602-5614
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Abstract
Efficient polymer-protein conjugation is a crucial step in the design of many therapeutic protein formulations including nanoscopic vaccine formulations, antibody-drug conjugates and to enhance the in vivo behaviour of proteins. Here we aimed at preparing well-defined polymers for conjugation to proteins by reversible addition-fragmentation chain transfer (RAFT) polymerization of both acrylates and methacrylamides with protein-reactive chain transfer agents (CTAs). These RAFT agents contain either a N-hydroxy-succinimide (NHS) or pentafluorophenyl (PFP) ester moiety that can be conjugated to lysine residues, and alternatively a maleimide (MAL) or pyridyl disulfide (PDS) moiety that can be conjugated to cysteine residues. Efficiency of the bioconjugation of these polymers to bovine and avian serum albumin was investigated as a function of stoichiometry, polymer molecular weight and the presence of reducing agents. A large molar excess of polymer was required to obtain an acceptable degree of protein conjugation. However, protein modification with N-succinimidyl-S-acetylthiopropionate (SATP) to introduce sulfhydryl groups onto primary amines, significantly increased conjugation efficiency with MAL- and PDS-containing polymers.
Keywords
THERMORESPONSIVE PROPERTIES, LIVING RADICAL POLYMERIZATION, HETEROTELECHELIC POLYMERS, PENTAFLUOROPHENYL ESTERS, 2-METHOXYETHYL ACRYLATE, 2-HYDROXYETHYL ACRYLATE, NANOPARTICLE VACCINES, SYNTHETIC VACCINES, DIBLOCK COPOLYMER, HPMA COPOLYMERS

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Citation

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MLA
Vanparijs, Nane et al. “Polymer-protein Conjugation via a ‘Grafting to’ Approach: a Comparative Study of the Performance of Protein-reactive RAFT Chain Transfer Agents.” POLYMER CHEMISTRY 6.31 (2015): 5602–5614. Print.
APA
Vanparijs, N., Maji, S., Louage, B., Voorhaar, L., Laplace, D., Zhang, Q., Shi, Y., et al. (2015). Polymer-protein conjugation via a “grafting to” approach: a comparative study of the performance of protein-reactive RAFT chain transfer agents. POLYMER CHEMISTRY, 6(31), 5602–5614.
Chicago author-date
Vanparijs, Nane, Samarendra Maji, Benoit Louage, Lenny Voorhaar, Duchan Laplace, Qilu Zhang, Y Shi, Wim E Hennink, Richard Hoogenboom, and Bruno De Geest. 2015. “Polymer-protein Conjugation via a ‘Grafting to’ Approach: a Comparative Study of the Performance of Protein-reactive RAFT Chain Transfer Agents.” Polymer Chemistry 6 (31): 5602–5614.
Chicago author-date (all authors)
Vanparijs, Nane, Samarendra Maji, Benoit Louage, Lenny Voorhaar, Duchan Laplace, Qilu Zhang, Y Shi, Wim E Hennink, Richard Hoogenboom, and Bruno De Geest. 2015. “Polymer-protein Conjugation via a ‘Grafting to’ Approach: a Comparative Study of the Performance of Protein-reactive RAFT Chain Transfer Agents.” Polymer Chemistry 6 (31): 5602–5614.
Vancouver
1.
Vanparijs N, Maji S, Louage B, Voorhaar L, Laplace D, Zhang Q, et al. Polymer-protein conjugation via a “grafting to” approach: a comparative study of the performance of protein-reactive RAFT chain transfer agents. POLYMER CHEMISTRY. 2015;6(31):5602–14.
IEEE
[1]
N. Vanparijs et al., “Polymer-protein conjugation via a ‘grafting to’ approach: a comparative study of the performance of protein-reactive RAFT chain transfer agents,” POLYMER CHEMISTRY, vol. 6, no. 31, pp. 5602–5614, 2015.
@article{6973396,
  abstract     = {Efficient polymer-protein conjugation is a crucial step in the design of many therapeutic protein formulations including nanoscopic vaccine formulations, antibody-drug conjugates and to enhance the in vivo behaviour of proteins. Here we aimed at preparing well-defined polymers for conjugation to proteins by reversible addition-fragmentation chain transfer (RAFT) polymerization of both acrylates and methacrylamides with protein-reactive chain transfer agents (CTAs). These RAFT agents contain either a N-hydroxy-succinimide (NHS) or pentafluorophenyl (PFP) ester moiety that can be conjugated to lysine residues, and alternatively a maleimide (MAL) or pyridyl disulfide (PDS) moiety that can be conjugated to cysteine residues. Efficiency of the bioconjugation of these polymers to bovine and avian serum albumin was investigated as a function of stoichiometry, polymer molecular weight and the presence of reducing agents. A large molar excess of polymer was required to obtain an acceptable degree of protein conjugation. However, protein modification with N-succinimidyl-S-acetylthiopropionate (SATP) to introduce sulfhydryl groups onto primary amines, significantly increased conjugation efficiency with MAL- and PDS-containing polymers.},
  author       = {Vanparijs, Nane and Maji, Samarendra and Louage, Benoit and Voorhaar, Lenny and Laplace, Duchan and Zhang, Qilu and Shi, Y and Hennink, Wim E and Hoogenboom, Richard and De Geest, Bruno},
  issn         = {1759-9954},
  journal      = {POLYMER CHEMISTRY},
  keywords     = {THERMORESPONSIVE PROPERTIES,LIVING RADICAL POLYMERIZATION,HETEROTELECHELIC POLYMERS,PENTAFLUOROPHENYL ESTERS,2-METHOXYETHYL ACRYLATE,2-HYDROXYETHYL ACRYLATE,NANOPARTICLE VACCINES,SYNTHETIC VACCINES,DIBLOCK COPOLYMER,HPMA COPOLYMERS},
  language     = {eng},
  number       = {31},
  pages        = {5602--5614},
  title        = {Polymer-protein conjugation via a 'grafting to' approach: a comparative study of the performance of protein-reactive RAFT chain transfer agents},
  url          = {http://dx.doi.org/10.1039/C4PY01224K},
  volume       = {6},
  year         = {2015},
}

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