Fully Protected Glycosylated Zinc (II) Phthalocyanine Shows High Uptake and Photodynamic Cytotoxicity in MCF-7 Cancer Cells

Authors

  • Stanley G. Kimani,

    1. Department of Life, Health and Chemical sciences, The Open University, Milton Keynes, UK
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    • Current address: MGH Wellman Center for Photomedicine, Boston, MA

  • Tatiana A. Shmigol,

    1. Department of Medical and Biological Physics, N.I. Pirogov Russian National Research Medical University, and Photomedicine Laboratory, Basic & Applied Biomedical Research Institute, Moscow, Russia
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  • Samantha Hammond,

    1. Department of Environment, Earth and Ecosystems, The Open University, Milton Keynes, UK
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  • James B. Phillips,

    1. Department of Life, Health and Chemical sciences, The Open University, Milton Keynes, UK
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  • James I. Bruce,

    1. Department of Life, Health and Chemical sciences, The Open University, Milton Keynes, UK
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  • Alexander J. MacRobert,

    1. National Medical Laser Centre, University College, London, UK
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  • Mikhail V. Malakhov,

    1. Department of Medical and Biological Physics, N.I. Pirogov Russian National Research Medical University, and Photomedicine Laboratory, Basic & Applied Biomedical Research Institute, Moscow, Russia
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  • Jon P. Golding

    Corresponding author
    1. Department of Life, Health and Chemical sciences, The Open University, Milton Keynes, UK
      Corresponding author email: j.p.golding@open.ac.uk (Jon Golding)
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Corresponding author email: j.p.golding@open.ac.uk (Jon Golding)

Abstract

Phthalocyanine photosensitizers are effective in anticancer photodynamic therapy (PDT) but suffer from limited solubility, limited cellular uptake and limited selectivity for cancer cells. To improve these characteristics, we synthesized isopropylidene-protected and partially deprotected tetra β-glycosylated zinc (II) phthalocyanines and compared their uptake and accumulation kinetics, subcellular localization, in vitro photocytotoxicity and reactive oxygen species generation with those of disulfonated aluminum phthalocyanine. In MCF-7 cancer cells, one of the compounds, zinc phthalocyanine {4}, demonstrated 10-fold higher uptake, 5-fold greater PDT-induced cellular reactive oxygen species concentration and 2-fold greater phototoxicity than equimolar (9 μm) disulfonated aluminum phthalocyanine. Thus, isopropylidene-protected β-glycosylation of phthalocyanines provides a simple method of improving the efficacy of PDT.

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