Novel heterotopic colloids of anionic porphyrins entangled in cationic amphiphilic cyclodextrins: spectroscopic investigation and intracellular delivery.
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.
Mazzaglia
Antonino
A
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
Angelini
Nicola
N
Darcy
Raphael
R
Donohue
Ruth
R
Lombardo
Domenico
D
Micali
Norberto
N
Sciortino
Maria Teresa
MT
Villari
Valentina
V
Scolaro
Luigi Monsù
LM
D000818:Animals; D000838:Anions; D002412:Cations; D045744:Cell Line, Tumor; D002942:Circular Dichroism / Q000379:methods; D003102:Colloids / Q000737:chemistry / Q000378:metabolism; D003505:Cyclodextrins / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D017136:Ion Transport; D008856:Microscopy, Fluorescence / Q000379:methods; D011166:Porphyrins / Q000737:chemistry* / Q000378:metabolism; D012995:Solubility; D013050:Spectrometry, Fluorescence / Q000379:methods; D013054:Spectrophotometry, Atomic / Q000379:methods; D013057:Spectrum Analysis / Q000379:methods; D014867:Water / Q000737:chemistry
D000838:Anions; D002412:Cations; D003102:Colloids; D003505:Cyclodextrins; D011166:Porphyrins; D014867:Water; C016136:tetraphenylporphine sulfonate