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Synthesis of Pyridyl Disulfide-Functionalized Nanoparticles for Conjugating Thiol-Containing Small Molecules, Peptides, and Proteins

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Institute of Bioengineering (IBI) and Institute of Chemical Sciences and Engineering (ISIC), Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne CH-1015, Switzerland
* To whom correspondence should be addressed. Address: Laboratory for Regenerative Medicine and Pharmacobiology, Institute of Bioengineering, Station 15, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, CH-1015, Switzerland. E-mail: [email protected]. Phone: +41 21 693 9681. Fax: +41 21 693 9665.
†Institute of Bioengineering (IBI).
‡Institute of Chemical Sciences and Engineering (ISIC).
Cite this: Bioconjugate Chem. 2010, 21, 4, 653–662
Publication Date (Web):April 6, 2010
https://doi.org/10.1021/bc9004443
Copyright © 2010 American Chemical Society
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    Abstract

    Previously we reported emulsion polymerization of propylene sulfide with Pluronic F127 as an emulsifier, yielding nanoparticles (NPs) in the 25 nm size range. Immunologically functional NPs were prepared by adding an antigen−Pluronic conjugate to the polymerization mixture (Reddy, S. T., et al. (2007) Nat. Biotechnol.25, 1159). We sought a more flexible scheme for conjugation of antigens and other biomolecules to the NP surfaces that would allow for milder reaction conditions than achievable during the polymerization step. Here, we present the synthesis of such functionalizable NPs in the form of NPs that carry thiol-reactive groups, to which thiol-containing antigens (peptide or protein) or other biomolecules can be conjugated under mild conditions to yield immunofunctional NPs. The Pluronic-stabilized poly(propylene sulfide) (PPS) NPs with thiol-reactive pyridyl disulfide groups are prepared in two steps by (1) emulsion polymerization of propylene sulfide in the presence of a carboxylate-Pluronic and (2) reaction of the carboxylic acid groups on the NP surface with cysteamine pyridyl disulfide and a water-soluble carbodiimide reagent. We choose pyridyl disulfide groups to have a reduction-sensitive disulfide bond linking the antigen to the NP surface, allowing efficient release of antigen inside the cell in response to the reductive conditions within the endosome. The functionalizable NPs are characterized by proton NMR, dynamic light scattering (DLS), UV/vis spectroscopy, and transmission electron microscopy (TEM). Conjugation of small molecules and protein to the NP surface is presented.

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    Calculation of NP composition, NMR spectra of 6 and pyridyl disulfide-NP, and estimation of numbers of biotin, peptide, and OVA molecules per NP. This material is available free of charge via the Internet at http://pubs.acs.org.

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