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Synthesis and photophysical properties of the photoactivatable cationic porphyrin 5-(4-N-dodecylpyridyl)-10,15,20-tri(4-N-methylpyridyl)-21H,23H-porphyrin tetraiodide for anti-malaria PDT

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Abstract

This article describes a new synthetic method for obtaining three water soluble porphyrins. The more sophisticated porphyrin [5-(4-N-dodecylpyridyl)-10,15,20-tri(4-N-methylpyridyl)-21H,23H-porphyrin tetraiodide], also named C12 porphyrin, was obtained through a three step methodology. The improvements, compared to syntheses described in the literature, mostly concern the purification procedures. The photophysical properties of the three porphyrins are described and the C12 porphyrin presents a very good 1O2 yield compared to its chemical intermediates. This porphyrin seems to be a very promising candidate for PDT applications.

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Authors and Affiliations

  1. Laboratoire Réactions et Génie des Procédés (LRGP), Université de Lorraine, UMR 7274, 1 rue Grandville, BP 20451, Nancy Cedex, France

    Aurélie Stallivieri, Florent Le Guern, Esme Meledje & Céline Frochot

  2. Laboratoire Réactions et Génie des Procédés (LRGP), CNRS, UMR 7274, 1 rue Grandville, BP 20451, Nancy Cedex, France

    Aurélie Stallivieri, Florent Le Guern, Esme Meledje & Céline Frochot

  3. Laboratoire de Chimie Physique Macromoléculaire (LCPM), Université de Lorraine, UMR 7375, 1 rue Grandville, BP 20451, Nancy Cedex, France

    Florent Le Guern, Régis Vanderesse, Esme Meledje & Samir Acherar

  4. Laboratoire de Chimie Physique Macromoléculaire (LCPM), CNRS, UMR 7375, 1 rue Grandville, BP 20451, Nancy Cedex, France

    Florent Le Guern, Régis Vanderesse, Esme Meledje & Samir Acherar

  5. Department of Biology, University of Padova, via U. Bassi 58/B, 35131, Padova, Italy

    Giulio Jori

Authors
  1. Aurélie Stallivieri
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  2. Florent Le Guern
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  3. Régis Vanderesse
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  4. Esme Meledje
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  5. Giulio Jori
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  6. Céline Frochot
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  7. Samir Acherar
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Corresponding author

Correspondence to Samir Acherar.

Additional information

This paper is dedicated to Giulio Jori who involved us in this project using PDT to fight against malaria.

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Stallivieri, A., Le Guern, F., Vanderesse, R. et al. Synthesis and photophysical properties of the photoactivatable cationic porphyrin 5-(4-N-dodecylpyridyl)-10,15,20-tri(4-N-methylpyridyl)-21H,23H-porphyrin tetraiodide for anti-malaria PDT. Photochem Photobiol Sci 14, 1290–1295 (2015). https://doi.org/10.1039/c5pp00139k

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  • DOI: https://doi.org/10.1039/c5pp00139k

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