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- Title
Rhenium(I) Polypyridine Diamine Complexes as Intracellular Phosphorogenic Sensors: Synthesis, Characterization, Emissive Behavior, Biological Properties, and Nitric Oxide Sensing.
- Authors
Choi, Alex Wing‐Tat; Yim, Vicki Man‐Wai; Liu, Hua‐Wei; Lo, Kenneth Kam‐Wing
- Abstract
We report the development of a series of rhenium(I) polypyridine complexes appended with an electron-rich diaminoaromatic moiety as phosphorogenic sensors for nitric oxide (NO). The diamine complexes [Re(N^N)(CO)3(py-DA)][PF6] (py-DA=3-( N-(2-amino-5-methoxyphenyl)aminomethyl)pyridine; N^N=1,10-phenanthroline (phen) ( 1 a), 3,4,7,8-tetramethyl-1,10-phenanthroline (Me4-phen) ( 2 a), 4,7-diphenyl-1,10-phenanthroline (Ph2-phen) ( 3 a)) have been synthesized and characterized. In contrast to common rhenium(I) diimines, these diamine complexes were very weakly emissive due to quenching of the triplet metal-to-ligand charge-transfer (3MLCT) emission by the diaminoaromatic moiety through photoinduced electron transfer (PET). Upon treatment with NO, the complexes were converted into the triazole derivatives [Re(N^N)(CO)3(py-triazole)][PF6] (py-triazole=3-((6-methoxybenzotriazol-1-yl)methyl)pyridine; N^N=phen ( 1 b), Me4-phen ( 2 b), Ph2-phen ( 3 b)), resulting in significant emission enhancement ( I/ I0≈60). The diamine complexes exhibited high reaction selectivity to NO, and their emission intensity was found to be independent on pH. Also, these complexes were effectively internalized by HeLa cells and RAW264.7 macrophages with negligible cytotoxicity. Additionally, the use of complex 3 a as an intracellular phosphorogenic sensor for NO has been demonstrated.
- Subjects
POLYPYRIDINES; RHENIUM; TRIAZOLES synthesis; CELL-mediated cytotoxicity; PHOTOINDUCED electron transfer
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 31, p9633
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201402502