Novel heterotopic colloids of anionic porphyrins entangled in cationic amphiphilic cyclodextrins: spectroscopic investigation and intracellular delivery |
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Authors: | Mazzaglia Antonino Angelini Nicola Darcy Raphael Donohue Ruth Lombardo Domenico Micali Norberto Sciortino Maria Teresa Villari Valentina Scolaro Luigi Monsù |
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Institution: | Istituto per lo Studio dei Materiali Nanostrutturati, ISMN-CNR, Unità di Messina, Dipartimento di Chimica Inorganica, Chimica Analitica e Chimica Fisica, Università di Messina and INFM, Salita Sperone 31, 98166 Messina, Italy. mazzaglia@chem.unime.it |
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Abstract: | The entanglement process between water-soluble 5,10,15,20-tetrakis(4-sulfonatophenyl)-21H,23H-porphine and the amphiphilic cyclodextrin (CD) heptakis(2-omega-amino-O-oligo(ethylene oxide)-6-hexylthio)-beta-CD and the occurrence of various species at different porphyrin:CD ratios were studied by a combination of UV/Vis absorption, fluorescence anisotropy, time-resolved fluorescence, resonance light scattering, and circular dichroism. The effect of the entanglement process on the mean vesicle diameter was investigated over a wide concentration range by quasielastic light-scattering techniques. The experimental results indicate that the presence of porphyrins in this colloidal system promotes some structural rearrangements, essentially driven by charge interaction, which are responsible for a sensitive change of vesicle dimensions. In the range of porphyrin:CD molar ratios between 1:10 and 1:50, the porphyrin is solubilized in monomeric form (tau(1)=11.5 ns) and photosensitizes the production of singlet oxygen ((1)O(2)). At the same molar ratio the ability of this amphiphilic cyclodextrin to transport porphyrins into tumor cells indicates specificity at the nuclear-compartment level. These findings may be of potential interest for the of development agents for photodynamic therapy of tumors. |
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Keywords: | cyclodextrins drug delivery fluorescence spectroscopy nanostructures porphyrinoids |
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