Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 17, Pages 6004-6010Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob05415e
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Funding
- Research Grants Council of the Hong Kong SAR, P.R. China [HKBU 202308, HKBU 202509]
- Hong Kong Baptist University [FRG2/08-09/067]
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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 beta-position with a hydrophilic Ru(II) polypyridyl complex, showed high singlet oxygen quantum yields (> 70%) and substantial two-photon absorption cross-sections (similar to 500 GM). Ru-L gave strong emissions at similar to 660 and similar to 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.
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