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Issue 127, 2015
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Porphyrin-uptake in liposomes and living cells using an exchange method with cyclodextrin

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Abstract

The water-solubilisation of porphyrin derivatives is very important for biological applications. Although liposomal drug carriers for porphyrin derivatives have shown significant promise in the field of medicinal chemistry (e.g., as sensitisers for photodynamic therapy), it is currently not possible to prepare lipid-membrane-incorporated tetraphenylporphyrin (TPP) with a high concentration of TPP using conventional methods. In this study, we have succeeded in preparing lipid-membrane-incorporated TPP and zinc(II) tetraphenylporphyrin (ZnTPP) from the corresponding TPP or ZnTPP·cyclodextrin complex using the exchange method in lipid-membranes composed of liposomes. Furthermore, the exchange method allowed for the incorporation of TPP or ZnTPP into the plasma membranes of HeLa cells. However, it was not possible to prepare lipid-membrane-incorporated porphyrin derivatives with polar and hydrophilic groups in the meso positions using this exchange reaction.

Graphical abstract: Porphyrin-uptake in liposomes and living cells using an exchange method with cyclodextrin

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Publication details

The article was received on 25 Nov 2015, accepted on 27 Nov 2015 and first published on 08 Dec 2015


Article type: Paper
DOI: 10.1039/C5RA24985F
Citation: RSC Adv., 2015,5, 105279-105287
  • Open access: Creative Commons BY license
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    Porphyrin-uptake in liposomes and living cells using an exchange method with cyclodextrin

    A. Ikeda, S. Hino, T. Mae, Y. Tsuchiya, K. Sugikawa, M. Tsukamoto, K. Yasuhara, H. Shigeto, H. Funabashi, A. Kuroda and M. Akiyama, RSC Adv., 2015, 5, 105279
    DOI: 10.1039/C5RA24985F

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