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“Clicking” Porphyrins to Magnetic Nanoparticles for Photodynamic Therapy

Authors

  • Merlyn Thandu,

    1. Department of Chemistry, Physics and Environment, University of Udine, Via del Cotonificio 108, 33100 Udine (Italy)
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  • Dr. Valentina Rapozzi,

    1. Department of Medical and Biological Sciences, School of Medicine, University of Udine, Piazzale Kolbe 4, 33100 Udine (Italy)
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  • Prof. Dr. Luigi Xodo,

    1. Department of Medical and Biological Sciences, School of Medicine, University of Udine, Piazzale Kolbe 4, 33100 Udine (Italy)
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  • Prof. Dr. Fernando Albericio,

    Corresponding author
    1. CIBER-BBN, Networking Centre on Bioengineering, Biomaterials, and Nanomedicine, Institute for Research in Biomedicine (IRB-Barcelona), Baldiri Reixac 10, 08028 Barcelona (Spain)
    2. Department of Organic Chemistry, University of Barcelona, 08028 Barcelona (Spain)
    3. School of Chemistry and Physics, University of KwaZulu-Natal, 4001 Durban (South Africa)
    • Fernando Albericio, CIBER-BBN, Networking Centre on Bioengineering, Biomaterials, and Nanomedicine, Institute for Research in Biomedicine (IRB-Barcelona), Baldiri Reixac 10, 08028 Barcelona (Spain)

      Clara Comuzzi, Department of Chemistry, Physics and Environment, University of Udine, Via del Cotonificio 108, 33100 Udine (Italy)

      Silvia Cavalli, Department of Chemistry, Physics and Environment, University of Udine, Via del Cotonificio 108, 33100 Udine (Italy)

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  • Dr. Clara Comuzzi,

    Corresponding author
    1. Department of Chemistry, Physics and Environment, University of Udine, Via del Cotonificio 108, 33100 Udine (Italy)
    • Fernando Albericio, CIBER-BBN, Networking Centre on Bioengineering, Biomaterials, and Nanomedicine, Institute for Research in Biomedicine (IRB-Barcelona), Baldiri Reixac 10, 08028 Barcelona (Spain)

      Clara Comuzzi, Department of Chemistry, Physics and Environment, University of Udine, Via del Cotonificio 108, 33100 Udine (Italy)

      Silvia Cavalli, Department of Chemistry, Physics and Environment, University of Udine, Via del Cotonificio 108, 33100 Udine (Italy)

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  • Dr. Silvia Cavalli

    Corresponding author
    1. Department of Chemistry, Physics and Environment, University of Udine, Via del Cotonificio 108, 33100 Udine (Italy)
    2. CIBER-BBN, Networking Centre on Bioengineering, Biomaterials, and Nanomedicine, Institute for Research in Biomedicine (IRB-Barcelona), Baldiri Reixac 10, 08028 Barcelona (Spain)
    3. Current address: Center for Advanced Biomaterials for Health Care IIT@CRIB, Istituto Italiano di Tecnologia, Largo Barsanti e Matteucci 53, 80125 Naples (Italy)
    • Fernando Albericio, CIBER-BBN, Networking Centre on Bioengineering, Biomaterials, and Nanomedicine, Institute for Research in Biomedicine (IRB-Barcelona), Baldiri Reixac 10, 08028 Barcelona (Spain)

      Clara Comuzzi, Department of Chemistry, Physics and Environment, University of Udine, Via del Cotonificio 108, 33100 Udine (Italy)

      Silvia Cavalli, Department of Chemistry, Physics and Environment, University of Udine, Via del Cotonificio 108, 33100 Udine (Italy)

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Abstract

A method for the preparation of superparamagnetic iron oxide nanoparticle–porphyrin (SPION-TPP) conjugates through click chemistry, which can be used as novel theranostic nanoagents for photodynamic therapy is developed. The synthesis, characterisation, and evaluation of the photocytotoxicity profiles of the nanoconjugates prepared is reported. Upon light irradiation, SPION-TPP nanoconstructs promote a photodynamic effect in vitro in murine amelanotic melanoma B78-H1 cells, with IC50 values in the region of 800 nM, similarly to unbound TPP, whereas they remain non-cytotoxic in the dark. However, these nanoconstructs show poor cellular uptake, which influences a linear dose–response effect. Therefore, the improvement of delivery to cells has also been studied by conjugating a well-known cell-penetrating peptide (TAT peptide) to the SPION-TPP nanoparticles. The new nanoconstructs show lower IC50 values (in the region of 500 nM) and a clear dose–response effect. Our results suggest that TAT-conjugated SPION-TPP nanoparticles are efficient nanodevices both for tracking drugs by means of magnetic resonance imaging (MRI)-based techniques and for treating cancer cells through photodynamic therapy, thus functioning as promising theranostic nanoagents.

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