Selective Fluorescence Quenching of 2,3-Diazabicyclo[2.2.2]oct-2-ene by Nucleotides

The fluorescence quenching of 2,3-diazabicyclo[2.2.2]oct-2-ene (DBO) by nucleotides has been studied. The quenching mechanism was analyzed on the basis of deuterium isotope effects, tendencies for exciplex formation, and the quenching efficiency in the presence of a molecular container (cucurbit[7]u...

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Published inOrganic letters Vol. 5; no. 21; pp. 3911 - 3914
Main Authors Marquez, Cesar, Pischel, Uwe, Nau, Werner M
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 16.10.2003
Subjects
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Fluorescence
Fluorescent Dyes - chemistry
Molecular Structure
Nucleotides - chemistry
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Summary:The fluorescence quenching of 2,3-diazabicyclo[2.2.2]oct-2-ene (DBO) by nucleotides has been studied. The quenching mechanism was analyzed on the basis of deuterium isotope effects, tendencies for exciplex formation, and the quenching efficiency in the presence of a molecular container (cucurbit[7]uril). Exciplex-induced quenching appears to prevail for adenosine, cytidine, and uridine, while hydrogen abstraction becomes competitive for thymidine and guanosine. Compared to other fluorescent probes, DBO responds very selectively to the type of nucleotide.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol035454q