Development of fast-response turn-on phosphorescent probes for biothiols based on ruthenium() complexes

A novel ruthenium( ii ) complex of [Ru(bpy) 2 (BIPP-DNBS)](ClO 4 ) 2 ( Ru-BIPP-DNBS ) {bpy = 2,2′-bipyridine, BIPP-DNBS = 4-bromo-2-(1 H -imidazo[4,5- f ][1,10]phenanthrolin-2-yl)phenyl 2,4-dinitrobenzenesulfonate} has been designed and synthesized as a fast-response turn-on phosphorescent probe for...

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Bibliographic Details
Published in:Analytical methods 2019-05, Vol.11 (17), p.2341-235
Main Authors: Zheng, Ze-Bao, Cui, Ji-Chun, Han, Yin-Feng, Ge, Yan-Qing, Zuo, Jian, Hao, Wen-Xin
Format: Article
Language:English
Subjects:
Detection limits
Electron transfer
Electrons
Glioma cells
Glutathione
Linearity
Phosphorescence
Ruthenium
Ruthenium compounds
Substitution reactions
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Summary:A novel ruthenium( ii ) complex of [Ru(bpy) 2 (BIPP-DNBS)](ClO 4 ) 2 ( Ru-BIPP-DNBS ) {bpy = 2,2′-bipyridine, BIPP-DNBS = 4-bromo-2-(1 H -imidazo[4,5- f ][1,10]phenanthrolin-2-yl)phenyl 2,4-dinitrobenzenesulfonate} has been designed and synthesized as a fast-response turn-on phosphorescent probe for the detection of biothiols. The ruthenium( ii ) polypyridine complex was used as a phosphorescence reporter and 2,4-dinitrobenzenesulfonate (DNBS) was used as both a recognition unit and phosphorescence quencher. Ru-BIPP-DNBS was weakly phosphorescent owing to the effectual photoinduced electron transfer (PET) from the ruthenium( ii ) luminophore to the sensing group DNBS. Upon treatment with biothiols, the 2,4-dinitrobenzenesulfonyl group of Ru-BIPP-DNBS was cleaved, and the phosphorescence was "turned on", as a result of the formation of Ru-BIPP . The favorable steric interactions between the 1 H -imidazo[4,5- f ][1,10]phenanthroline group and ortho -2,4-dinitrobenzenesulfonate highly ameliorated the response rate of Ru-BIPP-DNBS toward biothiols, resulting in a rapid thiol-induced S N Ar substitution reaction. This probe also exhibited good linearity ranges with detection limits of 0.47 μM for cysteine and 0.27 μM for glutathione. Furthermore, application of Ru-BIPP-DNBS for the imaging of endogenous biothiols in glioma cell samples was successfully demonstrated. A novel 2,4-dinitrobenzenesulfonyl appended ruthenium( ii ) complex acting as a fast-response "turn on" phosphorescent sensor for biothiols was successfully demonstrated.
ISSN:1759-9660
1759-9679
DOI:10.1039/c9ay00356h