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J Biol Inorg Chem ; 14(7): 1037-52, 2009 Sep.
Article in English | MEDLINE | ID: mdl-19471974

ABSTRACT

The novel gold porphyrin complex (5,10,15-tris(N-methylpyridinium-4-yl)-20-(1-pyrenyl)-porphyrinato)gold(III) chloride, [Au(III)(TMPy3Pyr1P)]Cl4, was prepared and characterized by optical spectroscopy, high-resolution nuclear magnetic resonance (NMR), and electrospray mass spectrometry. This cationic multichromophore compound exhibits excellent water solubility and does not form aggregates under physiological conditions. Binding interactions of this complex and related model compounds with nucleic acid substrates have been studied and characterized by NMR and circular dichroism spectroscopy. The photoreactivity of [Au(III)(TMPy3Pyr1P)]Cl4 was investigated under anaerobic and aerobic conditions in the presence of an excess of purine nucleoside, guanosine, and plasmid DNA. Photocatalytic oxidative degradation of guanosine and the change from supercoiled to circular plasmid DNA upon monochromatic irradiation and polychromatic blue-light exposure with a maximum at 420 nm was explored. The potential of the novel water-soluble cationic metallointercalator complex [Au(III)(TMPy3Pyr1P)]Cl4 to serve as a catalytic photonuclease for the cleavage of DNA has been demonstrated.


Subject(s)
Antineoplastic Agents/chemistry , DNA Breaks, Double-Stranded , DNA/chemistry , Gold/chemistry , Metalloporphyrins/chemistry , Organogold Compounds/chemistry , Photolysis , Photosensitizing Agents/chemistry , Antineoplastic Agents/chemical synthesis , Catalysis , Circular Dichroism , DNA/radiation effects , Deoxyguanine Nucleotides/chemistry , Deoxyguanine Nucleotides/radiation effects , Electrochemical Techniques , Guanosine/chemistry , Guanosine/radiation effects , Light , Magnetic Resonance Spectroscopy , Metalloporphyrins/chemical synthesis , Organogold Compounds/chemical synthesis , Photosensitizing Agents/chemical synthesis , Porphyrins/chemistry , Singlet Oxygen/chemistry , Solubility , Spectrometry, Fluorescence , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Ultraviolet , Transition Temperature
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