title: Two-photon induced luminescence, singlet oxygen generation, cellular uptake and photocytotoxic properties of amphiphilic Ru(II) polypyridyl-porphyrin conjugates as potential bifunctional photodynamic therapeutic agents.
abstract: Two Ru(II) polypyridyl-porphyrin and Zn(II) porphyrin conjugates (Ru-L and Ru-Zn-L) have been synthesized and their photophysical properties studied. The two conjugates, which contained a hydrophobic tetraphenylporphyrin L conjugated via an acetylide linker at its β-position with a hydrophilic Ru(II) polypyridyl complex, showed high singlet oxygen quantum yields (>70%) and substantial two-photon absorption cross-sections (~500 GM). Ru-L gave strong emissions at ~660 and ~733 nm through linear or two-photon excitation. Solvatochromism was observed in the fluorescence spectra of Ru-L and Ru-Zn-L, where in less polar solvents (i.e., toluene and dichloromethane) their fluorescence emissions became slightly blue-shifted with a 3-fold reduction in intensity relative to those observed in polar solvents (i.e., acetonitrile and methanol). Cell-based studies of these complex conjugates were conducted using human nasopharyngeal carcinoma HK-1 and cervical carcinoma HeLa cells on which Ru-L showed rapid cellular uptake, low dark-cytotoxicity, and high photo-cytotoxicity. Furthermore, Ru-L can be excited and emits in the "biological window"in vitro, making it a potential potent new generation photodynamic therapeutic agent capable of singlet oxygen generation and in vitro near-infrared emission.
authors: Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR, P. R. China.
authors: JingXiang
authors: J
authors: Zhang
authors: Ka-Leung
authors: KL
authors: Wong
authors: Wai-Kwok
authors: WK
authors: Wong
authors: Nai-Ki
authors: NK
authors: Mak
authors: Daniel W J
authors: DW
authors: Kwong
authors: Hoi-Lam
authors: HL
authors: Tam
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D045744:Cell Line, Tumor; D003603:Cytotoxins / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D006801:Humans; D049449:Luminescence; D008665:Metalloporphyrins / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology*; D009369:Neoplasms / Q000188:drug therapy; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology*; D026082:Singlet Oxygen / Q000378:metabolism*
chemical_list: D000970:Antineoplastic Agents; D003603:Cytotoxins; D008665:Metalloporphyrins; D017319:Photosensitizing Agents; C568421:Ru(II) polypyridyl-porphyrin; C568420:Ru-Zn-polypyridyl-porphyrin; D026082:Singlet Oxygen