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Photosensitized Oxidation of Hypoxanthine and Xanthine by Aluminum Phthalocyanine Tetrasulfonate. Role of the Alkylating Quinone 2,5‐Dichloro‐diaziridinyl‐1,4‐benzoquinone
Author(s) -
Alegria Antonio E.,
Inostroza Yaritza,
Kumar Ajay
Publication year - 2008
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.2008.00389.x
Subject(s) - chemistry , hypoxanthine , xanthine , quinone , photochemistry , singlet oxygen , semiquinone , benzoquinone , adduct , phthalocyanine , aqueous solution , dna , photodissociation , quenching (fluorescence) , rose bengal , oxygen , stereochemistry , organic chemistry , fluorescence , biochemistry , enzyme , physics , quantum mechanics
Photoirradiation of nitrogen‐saturated aqueous solutions containing aluminum phthalocyanine tetrasulfonate (AlPcS 4 ) at 675 nm in the presence of 2,5‐dichloro‐diaziridinyl‐1,4‐benzoquinone (AZDClQ) and hypoxanthine (HX) produces the oxidized HX derivatives, xanthine (X) and uric acid (UA). Concentrations of the AZDClQ semiquinone, X and UA increase at the expense of HX with an increase in irradiation time. Almost negligible decomposition of HX, as well as very low amounts of X, are detected if photolysis occurs under identical conditions but in the absence of AZDClQ. Addition of calf‐thymus DNA produces quinone‐DNA covalent adducts after photolysis of anaerobic samples containing quinone, DNA and AlPcS 4 , in the presence or absence of HX and at pH 5.5. However, larger amounts of quinone‐DNA adducts are detected if HX is present. The results presented here could have applications in the photodynamic treatment of hypoxic tissues such as solid tumors, under conditions of high HX concentration, where Type‐I pathways could be more important than singlet oxygen generation.