DOI QR코드

DOI QR Code

Polyvinyl butyral DMN-conjugates for the controlled release of singlet oxygen in medical and antimicrobial applications

  • Posavec, Damir (Institute of Inorganic Chemistry, Johannes Kepler University Linz (JKU)) ;
  • Muller, Rainer (Institute of Physical and Theoretical Chemistry, University of Regensburg) ;
  • Bogner, Udo (Institute of Physical and Theoretical Chemistry, University of Regensburg) ;
  • Bernhardt, Gunther (Institute of Pharmacy, University of Regensburg) ;
  • Knor, Gunther (Institute of Inorganic Chemistry, Johannes Kepler University Linz (JKU))
  • Received : 2013.12.17
  • Accepted : 2014.06.17
  • Published : 2014.06.25

Abstract

Covalent attachment of 1, 4-dimethylnaphthalene (DMN) based endoperoxide forming subunits to a polyvinyl butyral (PVB) backbone has been achieved. The functionalized polymer materials prepared and characterized here can serve as biocompatible carrier systems for studying cellular uptake, intermediate storage and delayed release of singlet oxygen, which opens up new doors for optimizing a variety of medical applications of photogenerated DMN-endoperoxides such as antiviral, antibacterial, antiplasmodial and antitumor activity.

Keywords

Acknowledgement

Grant : Sensory Photoreceptors in Natural and Artificial Systems

Supported by : DFG

References

  1. Antoni, P., Hed, Y., Nordberg, A., Nystrom, D., von Holst, H., Hult, A. and Malkoch, M. (2009), "Bifunctional dendrimers: from robust synthesis and accelerated one-pot postfunctionalization strategy to potential applications", Angew. Chem. Int. Ed., 48(12), 2126-2130. https://doi.org/10.1002/anie.200804987
  2. Bogner, U., Bernhardt, G. and Knor, G. (2011), "Material system comprising endoperoxide adapting to decomposition, and applications", WO2011/009903 A2.
  3. Duncan R . (2006), "Polymer Conjugates as Anticancer Nanomedicines", Nat. Rev. Cancer 6, 688-701. https://doi.org/10.1038/nrc1958
  4. Khandare, J. and Minko T. (2006), "Polymer-drug conjugates: progress in polymeric prodrugs", Prog. Polym. Sci., 31(4), 359-397. https://doi.org/10.1016/j.progpolymsci.2005.09.004
  5. Larson, N. and Ghandehari, H. (2012), "Polymeric conjugates for drug delivery", Chem. Mater., 24(5), 840-853. https://doi.org/10.1021/cm2031569
  6. Neises, B. and Steglich, W. (1978), "Simple method for the esterification of carboxylic acids", Angew. Chem. Int. Ed., 17(7), 522-524. https://doi.org/10.1002/anie.197805221
  7. Posavec, D., Zabel, M., Bogner, U., Bernhardt, G. and Knor, G. (2012), "Functionalized derivatives of 1,4- dimethylnaphthalene as precursors for biomedical applications: synthesis, structures, spectroscopy and photochemical activation in the presence of dioxygen", Org. Biomol. Chem., 10(35), 7062-7069. https://doi.org/10.1039/c2ob26236c
  8. Posavec, D., Dorsch, A., Bogner, U., Bernhardt, G. and Nagl, S. (2011), "Polyvinyl butyral nanobeads: preparation, characterization,biocompatibility and cancer cell uptake", Microchim. Act., 173(3-4), 391-399. https://doi.org/10.1007/s00604-011-0573-8
  9. Ringsdorf, H. (1975), "Structure and properties of pharmacologically active polymers", J. Polym. Sci. 51(1), 135-153.
  10. Schramm, C. and Rinderer, B. (2008), "Investigation of the hydrolysis of (3-triethoxysilylpropyl)succinic acid anhydride by means of FT-IR", J. Mater. Sci., 43(12), 4215-4219. https://doi.org/10.1007/s10853-008-2607-0
  11. Wang B., Galliford, C.V. and Low, P.S. (2014), "Guiding principles in the design of ligand-targeted nanomedicines", Nanomedicine, 9(2), 313-330. https://doi.org/10.2217/nnm.13.175