期刊
DALTON TRANSACTIONS
卷 44, 期 11, 页码 4945-4956出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4dt02890b
关键词
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资金
- Hong Kong Research Grants Council [CityU 7008174, 9667090]
We report the synthesis, characterisation and photophysical properties of new phosphorescent biscyclo-metallated iridium(III) ethylenediamine (en) complexes functionalised with polar ester or carboxylate groups [Ir(N boolean AND C)(2)(en)](n)(X) (n = +1, X = Cl-, HN boolean AND C = methyl 4-(2-pyridyl)benzoate Hppy-COOMe (1a), methyl 2-phenyl-4-quinolinecarboxylate Hpq-COOMe (2a); n = -1, X = Li+, HN boolean AND C = 4-(2-pyridyl) benzoate Hppy-COO- (1b), 2-phenyl-4-quinolinecarboxylate Hpq-COO- (2b)). In aqueous solutions, the carboxylate complexes 1b and 2b displayed emission quenching (ca. 7 and 74 fold, respectively) and lifetime shortening upon protonation, and their pK(a) values were determined to be 5.13 and 3.46, respectively. The pq complexes 2a and 2b exhibited hypsochromic shifts in their emission maxima and a significant increase in emission intensity (ca. 84 and 15 fold, respectively) upon nonspecific binding to the protein bovine serum albumin (BSA). Inductively coupled plasma-mass spectroscopy (ICP-MS) and laser-scanning confocal microscopy (LSCM) results revealed that the ester complexes 1a and 2a were efficiently internalised by the human cervix epithelioid carcinoma (HeLa) cells through energy-requiring pathways and subsequently localised in endosomes and mitochondria, respectively. They showed good biocompatibility in the dark, but became significantly cytotoxic upon photoirradiation due to the generation of singlet oxygen. In contrast, in aqueous solutions of physiological pH, the carboxylate complexes 1b and 2b existed as the anionic form and hardly entered cells due to limited membrane permeability, as evidenced by the intense emission surrounding the plasma membrane of the cells. They showed negligible cytotoxicity and the cell viability remained over 95% for an incubation period of 24 hours. In view of the low cytotoxicity and strongly emissive nature of the hydrophilic ppy-COO- complex 1b in an aqueous medium, the potential application of the complex as a visualisation reagent has been demonstrated using zebrafish (Danio rerio) as an animal model.
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