Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 13, Pages 6000-6005Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5005263
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Funding
- Ulsan National Institute of Science and Technology [1.120017.01, 1.120046.01, 1.130073.01]
- National Research Foundation (NRF) - Government of Korea (MSIP) [2013R1A1A2010877, 2009-0080734]
- National Research Foundation of Korea [2009-0080734, 2013R1A1A2010877] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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A bis[(4,6-difluorophenyl)pyridinato-N,C-2']iridium(III) picolinate (FIrpic) derivative coupled with bis(Zn2+-dipicolylamine) (ZnDPA) was developed as a sensor (1) for phosphorylated peptides, which are related to many cellular mechanisms. As a control, a fluorescent sensor (2) based on anthracene coupled to ZnDPA was also prepared. When the total negative charge on the phosphorylated peptides was changed to -2, -4, and -6, the emission intensity of sensor 1 gradually increased by factors of up to 7, 11, and 16, respectively. In contrast, there was little change in the emission intensity of sensor 1 upon the addition of a neutral phosphorylated peptide, non-phosphorylated peptides, or various anions such as CO32-, NO3-, SO42-, phosphate, azide, and pyrophosphate. Furthermore, sensor 1 could be used to visually discriminate between phosphorylated peptides and adenosine triphosphate in aqueous solution under a UV-vis lamp, unlike fluorescent sensor 2. This enhanced luminance of phosphorescent sensor 1 upon binding to a phosphorylated peptide is attributed to a reduction in the repulsion between the Zn2+ ions due to the phenoxy anion, its strong metal-to-ligand charge transfer character, and a reduction in self-quenching.
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