To control the activity of photosensitized singlet oxygen (1O2) generation, the electron donor-connecting porphyrin, 5-(9′-anthryl)-10,15,20-tris(p-pyridyl)porphyrin (AnTPyP), was designed and synthesized. AnTPyP became water-soluble by the protonation of the pyridyl moieties in the presence of 5 mm trifluoroacetic acid (pH 2.3). The photoexcited state of the porphyrin ring in an AnTPyP molecule was effectively deactivated by intramolecular electron transfer from the anthracene moiety within 0.04 ns in an aqueous solution. The deactivation was suppressed by the interaction with a DNA strand, resulting in the elongation of the lifetime of the porphyrin excited state and the enhancement of the fluorescence intensity. Furthermore, it was confirmed that the interaction enabled the photoexcited AnTPyP to generate 1O2. Selective 1O2 generation by forming a complex with DNA should be the initial step to realize the target selective photodynamic therapy.
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