Porphyrin‐uptake in liposomes and living cells using an exchange method with cyclodextrin
RSCAd_5-127_105279.pdf 2.22 MB
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.
Electronic supplementary information (ESI) available: Experimental procedures, 1H NMR spectra, DLS measurements, cryo-TEM images, phase contrast and fluorescence images. See DOI: 10.1039/c5ra24985
This work was supported by JSPS KAKENHI a Grant‐in‐Aid for Scientific Research (B) (Grant No. 25288037) and a Grant‐in‐Aid for Young Scientists (A) (Grant No. 24681028).
|date of issued||
Royal Society of Chemistry
This journal is © The Royal Society of Chemistry 2015
This is an open access article distributed under the terms of the Creative Commons Attribution 3.0 Unported Licence.
Graduate School of Engineering
Graduate School of Advanced Sciences of Matter