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Multifunctional poly(2-ethyl-2-oxazoline) copolymers containing dithiolane and pentafluorophenyl esters as effective reactive linkers for gold surface coatings

Ondrej Sedlacek (UGent) , Tim Egghe, Patricia Khashayar (UGent) , Martin Purino (UGent) , Paula Dias Lopes Campos (UGent) , Jan Vanfleteren (UGent) , Nathalie De Geyter (UGent) and Richard Hoogenboom (UGent)
(2023) BIOCONJUGATE CHEMISTRY. 34(12). p.2311-2318
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  • PoCOsteo (PoC in-office device for identifying individuals at high risk of Osteoporosis and osteoporotic fracture)
Abstract
Surface functionalization with biological macromolecules is an important task for the development of sensor materials, whereby the interaction with other biological materials should be suppressed. In this work, we developed a novel multifunctional poly-(2-ethyl-2-oxazoline)-dithiolane conjugate as a versatile linker for gold surface immobilization of amine-containing biomolecules, containing poly-(2-ethyl-2-oxazoline) as antifouling polymer, dithiolane for surface immobilization, and activated esters for protein conjugation. First, a well-defined carboxylic acid containing copoly-(2-ethyl-2-oxazoline) was synthesized by cationic ring-opening copolymerization of 2-ethyl-2-oxazoline with a methyl ester-containing 2-oxazoline monomer, followed by postpolymerization modifications. The side-chain carboxylic groups were then converted to amine-reactive pentafluorophenyl (PFP) ester groups. Part of the PFP groups was used for the attachment of the dithiolane moiety, which can efficiently bind to gold surfaces. The final copolymer contained 1.4 mol% of dithiolane groups and 4.5 mol% of PFP groups. The copolymer structure was confirmed by several analytical techniques, including NMR spectroscopy and size-exclusion chromatography. The kinetics of the PFP ester aminolysis and hydrolysis demonstrated significantly faster amidation compared to hydrolysis, which is essential for subsequent protein conjugation. Successful coating of gold surfaces with the polymer was confirmed by spectroscopic ellipsometry, showing a polymer brush thickness of 4.77 nm. Subsequent modification of the coated surfaces was achieved using bovine serum albumin as a model protein. This study introduces a novel reactive polymer linker for gold surface functionalization and offers a versatile polymer platform for various applications including biosensing and surface functionalization.
Keywords
Organic Chemistry, Pharmaceutical Science, Pharmacology, Biomedical Engineering, Bioengineering, Biotechnology, BRUSHES, POLY(2-OXAZOLINE)S, FUNCTIONALIZATION, POLYMERS

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Citation

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MLA
Sedlacek, Ondrej, et al. “Multifunctional Poly(2-Ethyl-2-Oxazoline) Copolymers Containing Dithiolane and Pentafluorophenyl Esters as Effective Reactive Linkers for Gold Surface Coatings.” BIOCONJUGATE CHEMISTRY, vol. 34, no. 12, 2023, pp. 2311–18, doi:10.1021/acs.bioconjchem.3c00444.
APA
Sedlacek, O., Egghe, T., Khashayar, P., Purino, M., Dias Lopes Campos, P., Vanfleteren, J., … Hoogenboom, R. (2023). Multifunctional poly(2-ethyl-2-oxazoline) copolymers containing dithiolane and pentafluorophenyl esters as effective reactive linkers for gold surface coatings. BIOCONJUGATE CHEMISTRY, 34(12), 2311–2318. https://doi.org/10.1021/acs.bioconjchem.3c00444
Chicago author-date
Sedlacek, Ondrej, Tim Egghe, Patricia Khashayar, Martin Purino, Paula Dias Lopes Campos, Jan Vanfleteren, Nathalie De Geyter, and Richard Hoogenboom. 2023. “Multifunctional Poly(2-Ethyl-2-Oxazoline) Copolymers Containing Dithiolane and Pentafluorophenyl Esters as Effective Reactive Linkers for Gold Surface Coatings.” BIOCONJUGATE CHEMISTRY 34 (12): 2311–18. https://doi.org/10.1021/acs.bioconjchem.3c00444.
Chicago author-date (all authors)
Sedlacek, Ondrej, Tim Egghe, Patricia Khashayar, Martin Purino, Paula Dias Lopes Campos, Jan Vanfleteren, Nathalie De Geyter, and Richard Hoogenboom. 2023. “Multifunctional Poly(2-Ethyl-2-Oxazoline) Copolymers Containing Dithiolane and Pentafluorophenyl Esters as Effective Reactive Linkers for Gold Surface Coatings.” BIOCONJUGATE CHEMISTRY 34 (12): 2311–2318. doi:10.1021/acs.bioconjchem.3c00444.
Vancouver
1.
Sedlacek O, Egghe T, Khashayar P, Purino M, Dias Lopes Campos P, Vanfleteren J, et al. Multifunctional poly(2-ethyl-2-oxazoline) copolymers containing dithiolane and pentafluorophenyl esters as effective reactive linkers for gold surface coatings. BIOCONJUGATE CHEMISTRY. 2023;34(12):2311–8.
IEEE
[1]
O. Sedlacek et al., “Multifunctional poly(2-ethyl-2-oxazoline) copolymers containing dithiolane and pentafluorophenyl esters as effective reactive linkers for gold surface coatings,” BIOCONJUGATE CHEMISTRY, vol. 34, no. 12, pp. 2311–2318, 2023.
@article{01HHEPH2TZNDQ9E26BAK7SXTAD,
  abstract     = {{Surface functionalization with biological macromolecules is an important task for the development of sensor materials, whereby the interaction with other biological materials should be suppressed. In this work, we developed a novel multifunctional poly-(2-ethyl-2-oxazoline)-dithiolane conjugate as a versatile linker for gold surface immobilization of amine-containing biomolecules, containing poly-(2-ethyl-2-oxazoline) as antifouling polymer, dithiolane for surface immobilization, and activated esters for protein conjugation. First, a well-defined carboxylic acid containing copoly-(2-ethyl-2-oxazoline) was synthesized by cationic ring-opening copolymerization of 2-ethyl-2-oxazoline with a methyl ester-containing 2-oxazoline monomer, followed by postpolymerization modifications. The side-chain carboxylic groups were then converted to amine-reactive pentafluorophenyl (PFP) ester groups. Part of the PFP groups was used for the attachment of the dithiolane moiety, which can efficiently bind to gold surfaces. The final copolymer contained 1.4 mol% of dithiolane groups and 4.5 mol% of PFP groups. The copolymer structure was confirmed by several analytical techniques, including NMR spectroscopy and size-exclusion chromatography. The kinetics of the PFP ester aminolysis and hydrolysis demonstrated significantly faster amidation compared to hydrolysis, which is essential for subsequent protein conjugation. Successful coating of gold surfaces with the polymer was confirmed by spectroscopic ellipsometry, showing a polymer brush thickness of 4.77 nm. Subsequent modification of the coated surfaces was achieved using bovine serum albumin as a model protein. This study introduces a novel reactive polymer linker for gold surface functionalization and offers a versatile polymer platform for various applications including biosensing and surface functionalization.}},
  author       = {{Sedlacek, Ondrej and Egghe, Tim and Khashayar, Patricia and Purino, Martin and Dias Lopes Campos, Paula and Vanfleteren, Jan and De Geyter, Nathalie and Hoogenboom, Richard}},
  issn         = {{1043-1802}},
  journal      = {{BIOCONJUGATE CHEMISTRY}},
  keywords     = {{Organic Chemistry,Pharmaceutical Science,Pharmacology,Biomedical Engineering,Bioengineering,Biotechnology,BRUSHES,POLY(2-OXAZOLINE)S,FUNCTIONALIZATION,POLYMERS}},
  language     = {{eng}},
  number       = {{12}},
  pages        = {{2311--2318}},
  title        = {{Multifunctional poly(2-ethyl-2-oxazoline) copolymers containing dithiolane and pentafluorophenyl esters as effective reactive linkers for gold surface coatings}},
  url          = {{http://doi.org/10.1021/acs.bioconjchem.3c00444}},
  volume       = {{34}},
  year         = {{2023}},
}
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