Selective fluorescence quenching of 2,3-diazabicyclo[2.2.2]oct-2-ene by nucleotides

Cesar Marquez; Uwe Pischel; Werner M Nau

doi:10.1021/ol035454q

Selective fluorescence quenching of 2,3-diazabicyclo[2.2.2]oct-2-ene by nucleotides

Org Lett. 2003 Oct 16;5(21):3911-4. doi: 10.1021/ol035454q.

Authors

Cesar Marquez¹, Uwe Pischel, Werner M Nau

Affiliation

¹ School of Engineering and Science, International University Bremen, Campus Ring 1, D-28759 Bremen, Germany.

PMID: 14535741
DOI: 10.1021/ol035454q

Abstract

[reaction: see text] 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Fluorescence
Fluorescent Dyes / chemistry*
Molecular Structure
Nucleotides / chemistry*

Substances

2,3-diazabicyclo(2.2.2)oct-2-ene
Bridged Bicyclo Compounds, Heterocyclic
Fluorescent Dyes
Nucleotides