A europium(III) complex as an efficient singlet oxygen luminescence probe.

Abstract

A new europium(III) complex, [4'-(10-methyl-9-anthryl)-2,2':6',2"-terpyridine-6,6"-diyl]bis(methylenenitrilo) tetrakis(acetate)-Eu(3+), was designed and synthesized as a highly sensitive and selective time-gated luminescence probe for singlet oxygen ((1)O2). The new probe is highly water soluble with a large stability constant of approximately 10(21) and a wide pH available range (pH 3-10), and can specifically react with (1)O2 to form its endoperoxide (EP-MTTA-Eu(3+)) with a high reaction rate constant at 10(10) M(-1) s(-1), accompanied by the remarkable increases of luminescence quantum yield from 0.90% to 13.8% and lifetime from 0.80 to 1.29 ms, respectively. The wide applicability of the probe was demonstrated by detection of (1)O2 generated from a MoO(4)(2-)/H(2)O2 system, a photosensitization system of 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin tetra(p-toluenesulfonate) (TMPyP), and a horseradish peroxidase catalyzed aerobic oxidation system of indole-3-acetic acid (IAA). In addition, it was found that the new probe could be easily transferred into living HeLa cells by incubation with TMPyP. A time-gated luminescence imaging technique that can fully eliminate the short-lived background fluorescence from TMPyP and cell components has been successfully developed for monitoring the time-dependent generation of (1)O2 in living cells.

• Authors: Bo Song, Guilan Wang, Mingqian Tan, Jingli Yuan
• Journal: Journal of the American Chemical Society (J Am Chem Soc) Vol. 128 Issue 41 Pg. 13442-50 (Oct 18 2006) ISSN: 0002-7863 [Print] United States
• PMID: 17031957 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• (4'-(10-methyl-9-anthryl)-2,2'-6',2''-terpyridine-6,6''-diyl)bis(methylenenitrilo) tetrakis(acetate)-Eu(3+)
• Cations
• Luminescent Agents
• Molecular Probes
• Organometallic Compounds
• Water
• Singlet Oxygen
• Europium
• Horseradish Peroxidase
• Oxygen

Topics

• Catalysis
• Cations
• Europium (chemistry)
• HeLa Cells
• Horseradish Peroxidase (metabolism)
• Humans
• Hydrogen-Ion Concentration
• Luminescent Agents (chemical synthesis)
• Luminescent Measurements
• Molecular Probes (chemical synthesis)
• Organometallic Compounds (chemical synthesis)
• Oxidation-Reduction
• Oxygen (chemistry, metabolism)
• Sensitivity and Specificity
• Singlet Oxygen (chemistry)
• Solubility
• Time Factors
• Water (chemistry)