title: Control of singlet oxygen generation photosensitized by meso-anthrylporphyrin through interaction with DNA.
abstract: To control the activity of photosensitized singlet oxygen ((1)O(2)) 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 (1)O(2). Selective (1)O(2) generation by forming a complex with DNA should be the initial step to realize the target selective photodynamic therapy.
authors.affiliation: Department of Basic Engineering (Chemistry), Faculty of Engineering, Shizuoka University, Shizuoka, Japan. tkhirak@ipc.shizuoka.ac.jp
authors.forename: Kazutaka
authors.initials: K
authors.lastname: Hirakawa
authors.forename: Toru
authors.initials: T
authors.lastname: Hirano
authors.forename: Yoshinobu
authors.initials: Y
authors.lastname: Nishimura
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Arai
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Nosaka
mesh_terms: D000873:Anthracenes / Q000737:chemistry* / Q000378:metabolism; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004247:DNA / Q000737:chemistry / Q000378:metabolism; D004579:Electron Transport / Q000187:drug effects / Q000528:radiation effects; D005453:Fluorescence; D006801:Humans; D008027:Light; D008958:Models, Molecular; D009369:Neoplasms / Q000188:drug therapy / Q000473:pathology; D009841:Oligonucleotides / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction / Q000187:drug effects / Q000528:radiation effects; D010777:Photochemistry / Q000379:methods*; D010778:Photochemotherapy / Q000379:methods*; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D011166:Porphyrins / Q000138:chemical synthesis* / Q000378:metabolism / Q000627:therapeutic use; D026082:Singlet Oxygen / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D014269:Trifluoroacetic Acid / Q000737:chemistry
chemical_list: D000873:Anthracenes; D000970:Antineoplastic Agents; D009841:Oligonucleotides; D017319:Photosensitizing Agents; D011166:Porphyrins; D026082:Singlet Oxygen; D004247:DNA; D014269:Trifluoroacetic Acid