Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 28, Pages 8329-8339Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000474
Keywords
DNA; iridium; luminescence; PEGylation probes
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Funding
- Hong Kong Research Grants Council [CityU 101908, 102109]
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We report the synthesis, characterization, and photophysical properties of a new class of luminescent cyclometalated iridium(III) polypyridine poly(ethylene glycol) (PEG) complexes [Ir(N boolean AND C)(2)(N boolean AND N)](PF6) (HN boolean AND C = Hppy (2-phenylpyridine), N boolean AND N = bpy- CONH PEG1 (bpy=2,2'-bipyridine; 1a), bpy-CONH-PEG3 (1b); HN boolean AND C = Hpq (2-phenylquinoline), N boolean AND N = bpy-CONH-PEG1 (2a), bpy- CONH-PEG3 (2b); HN boolean AND C=Hpba (4-(2-pyridyl)benzaldehyde), N boolean AND N =bpy- CONH PEG1 (3)) and their PEG-free counterparts (N boolean AND N=bpy-CONH-Et, HN boolean AND C=Hppy (1c); HN boolean AND C=Hpq (2c)). The cytotoxicity and cellular uptake of these complexes have been investigated by the MTT assay, ICPMS, laser-scanning confocal microscopy, and flow cytometry. The results showed that the complexes supported by the water-soluble PEG can act as biological probes and labels with considerably reduced cytotoxicity. Because the aldehyde groups of complex 3 are reactive toward primary amines, the complex has been utilized as the first luminescent PEGylation reagent. Bovine serum albumin (BSA) and poly(ethyleneimine) (PEI) have been PEGylated with this complex, and the resulting conjugates have been isolated, purified, and their photophysical properties studied. The DNA-binding and gene-delivery properties of the luminescent PEI conjugate 3-PEI have also been investigated.
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