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Issue 30, 2013
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Synthesis of thiolated and acrylated nanoparticles using thiol-ene click chemistry: towards novel mucoadhesive materials for drug delivery

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Abstract

Thiol- and acrylate-functionalized nanoparticles have been synthesized from pentaerythritol tetrakis(3-mercapto-propionate) and pentaerythritol tetraacrylate using thiol-ene click chemistry. Using Raman and 1H NMR spectroscopy as well as Ellman's assay, it was demonstrated that excess pentaerythritol tetraacrylate in the feed mixture led to nanoparticles with free acrylate groups on their surface, whereas nanoparticles with thiolated surfaces could be synthesized using feed mixtures with excess pentaerythritol tetrakis(3-mercapto-propionate). The possibility of fluorescent labelling of thiolated nanoparticles has been demonstrated through their reaction with fluorescein-5-maleimide. The thiolated nanoparticles were found to be mucoadhesive and exhibited retention on mucosal surface of porcine urinary bladder.

Graphical abstract: Synthesis of thiolated and acrylated nanoparticles using thiol-ene click chemistry: towards novel mucoadhesive materials for drug delivery

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Publication details

The article was received on 28 Apr 2013, accepted on 21 May 2013 and first published on 22 May 2013


Article type: Paper
DOI: 10.1039/C3RA42093K
Citation: RSC Adv., 2013,3, 12275-12279
  • Open access: Creative Commons BY-NC license
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    Synthesis of thiolated and acrylated nanoparticles using thiol-ene click chemistry: towards novel mucoadhesive materials for drug delivery

    A. Štorha, E. A. Mun and V. V. Khutoryanskiy, RSC Adv., 2013, 3, 12275
    DOI: 10.1039/C3RA42093K

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