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Thiolated Mucoadhesive and PEGylated Nonmucoadhesive Organosilica Nanoparticles from 3-Mercaptopropyltrimethoxysilane

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    Thiolated Mucoadhesive and PEGylated Nonmucoadhesive Organosilica Nanoparticles from 3-Mercaptopropyltrimethoxysilane
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    † Reading School of Pharmacy, University of Reading, Whiteknights, RG6 6AD Reading, United Kingdom
    † Department of Colloidal and Macromolecular Chemistry, al-Farabi Kazakh National University, Kazakhstan
    Fax: +44 (0) 118 378 4703; Tel: +44 (0) 118 378 6119; E-mail: [email protected]
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    Cite this: Langmuir 2011, 27, 15, 9551–9556
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    https://doi.org/10.1021/la201385h
    Published June 27, 2011
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    Abstract

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    A novel approach has been developed to synthesize thiolated sub-100 nm organosilica nanoparticles from 3-mercaptopropyltrimethoxysilane (MPTS) through its self-condensation in dimethylsulfoxide in contact with atmospheric oxygen. The formation of MPTS nanoparticles proceeds through the condensation of methoxysilane groups and simultaneous disulfide bridging caused by partial oxidation of thiol groups. These nanoparticles showed excellent colloidal stability in dilute aqueous dispersions but underwent further self-assembly into chains and necklaces at higher concentrations. They exhibited very good ability to adhere to ocular mucosal surfaces, which can find applications in drug delivery. The thiolated nanoparticles could also be easily modified through PEGylation resulting in a loss of their mucoadhesive properties.

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    Additional data on Raman spectra, dynamic light scattering size distributions, results of control experiments with fluorescence microscopy. This material is available free of charge via the Internet at http://pubs.acs.org.

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    78. Zhansaya A. Nurpeissova, Sholpan G. Alimkhanova, Rauash A. Mangazbayeva, Yerengaip M. Shaikhutdinov, Grigoriy A. Mun, Vitaliy V. Khutoryanskiy. Redox- and glucose-responsive hydrogels from poly(vinyl alcohol) and 4-mercaptophenylboronic acid. European Polymer Journal 2015, 69 , 132-139. https://doi.org/10.1016/j.eurpolymj.2015.06.003
    79. Edward D. H. Mansfield, Katy Sillence, Patrick Hole, Adrian C. Williams, Vitaliy V. Khutoryanskiy. POZylation: a new approach to enhance nanoparticle diffusion through mucosal barriers. Nanoscale 2015, 7 (32) , 13671-13679. https://doi.org/10.1039/C5NR03178H
    80. M. T. Cook, S. A. Schmidt, E. Lee, W. Samprasit, P. Opanasopit, V. V. Khutoryanskiy. Synthesis of mucoadhesive thiol-bearing microgels from 2-(acetylthio)ethylacrylate and 2-hydroxyethylmethacrylate: novel drug delivery systems for chemotherapeutic agents to the bladder. Journal of Materials Chemistry B 2015, 3 (32) , 6599-6604. https://doi.org/10.1039/C5TB00834D
    81. Peter WJ Morrison, Vitaliy V Khutoryanskiy. Advances in Ophthalmic Drug Delivery. Therapeutic Delivery 2014, 5 (12) , 1297-1315. https://doi.org/10.4155/tde.14.75
    82. Peter W.J. Morrison, Vitaliy V. Khutoryanskiy. Anatomy of the Eye and the Role of Ocular Mucosa in Drug Delivery. 2014, 39-60. https://doi.org/10.1002/9781118794203.ch02
    83. Flavia Laffleur, Andreas Bernkop-Schnürch. Strategies for Improving Mucosal Drug Delivery. Nanomedicine 2013, 8 (12) , 2061-2075. https://doi.org/10.2217/nnm.13.178
    84. Anna Štorha, Ellina A. Mun, Vitaliy V. Khutoryanskiy. Synthesis of thiolated and acrylated nanoparticles using thiol-ene click chemistry: towards novel mucoadhesive materials for drug delivery. RSC Advances 2013, 3 (30) , 12275. https://doi.org/10.1039/C3RA42093K
    85. Caroline A. Withers, Michael T. Cook, Lisa Methven, Margot A. Gosney, Vitaliy V. Khutoryanskiy. Investigation of milk proteins binding to the oral mucosa. Food & Function 2013, 4 (11) , 1668. https://doi.org/10.1039/c3fo60291e
    86. Richard A. Cave, Joseph P. Cook, Che J. Connon, Vitaliy V. Khutoryanskiy. A flow system for the on-line quantitative measurement of the retention of dosage forms on biological surfaces using spectroscopy and image analysis. International Journal of Pharmaceutics 2012, 428 (1-2) , 96-102. https://doi.org/10.1016/j.ijpharm.2012.02.047
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    Cite this: Langmuir 2011, 27, 15, 9551–9556
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    https://doi.org/10.1021/la201385h
    Published June 27, 2011
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