Photophysical properties and photodynamic activity of octacationic oxotitanium(IV) phthalocyanines.
The photophysical and photosensitizing properties of two octacationic oxotitanium phthalocyanines (TiOPcs), bearing pyridiniomethyl or cholinyl substituents, have been studied in aqueous and alcohol solutions. In water, both compounds were monomeric with the high quantum yields of fluorescence (Phi(F) = 0.17-0.19) and singlet oxygen formation (Phi(Delta) = 0.4-0.5). The Phi(F) and Phi(Delta) of both phthalocyanines decreased with the increase of solvent hydrophobicity from water to ethanol. This effect was much stronger in alcohol solutions of the pyridiniomethyl-substituted phthalocyanine and probably results from aggregation of TiOPc molecules caused by association of chloride anions with phthalocyanine cationic groups. Evidence is presented that under illumination aqueous TiOPc solutions also produce hydroxyl radicals, which probably appear owing to photocleavage of water molecules. The quantum yield of OH formation was (3-5) x 10(-5) after argon purging and twice as much in the presence of air. It is shown that irradiation of TiOPc solutions causes photobleaching of TiOPcs. The photobleaching quantum yield in water was found to be about 1 x 10(-4). The data suggest that photobleaching occurs owing to the reactivity of hydroxyl radicals, though singlet oxygen is generated by TiOPcs much more efficiently. The phototoxicity of the tested TiOPcs toward bacteria has been revealed. It is proposed that both OH and (1)O(2) might be responsible for the observed bactericidal effects.
Kuznetsova
Nina
N
Organic Intermediates and Dyes Institute, B. Sadovaya 1/4, Moscow, 123995, Russian Federation. jerrik@rol.ru
Makarov
Dmitry
D
Yuzhakova
Olga
O
Strizhakov
Anton
A
Roumbal
Yana
Y
Ulanova
Ludmila
L
Krasnovsky
Alexander
A
Kaliya
Oleg
O
D001419:Bacteria / Q000187:drug effects; D004578:Electron Spin Resonance Spectroscopy; D005453:Fluorescence; D057927:Hydrophobic and Hydrophilic Interactions; D017665:Hydroxyl Radical / Q000737:chemistry / Q000378:metabolism; D007211:Indoles / Q000737:chemistry*; D054833:Isoindoles; D008027:Light; D009942:Organometallic Compounds / Q000737:chemistry*; D017319:Photosensitizing Agents / Q000737:chemistry*; D026082:Singlet Oxygen / Q000737:chemistry / Q000378:metabolism; D013056:Spectrophotometry, Ultraviolet; D014025:Titanium / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D007211:Indoles; D054833:Isoindoles; D009942:Organometallic Compounds; D017319:Photosensitizing Agents; D014867:Water; D026082:Singlet Oxygen; D017665:Hydroxyl Radical; D014025:Titanium; C013647:phthalocyanine