Introduction of a nitroxide group on position 2 of 9-phenoxyacridine: Easy access to spin labelled DNA-binding conjugates

In the search for spin labelled intercalators of general use to construct DNA-binding conjugates, 6-chloro-2-[(1-oxyl-2,2,5,5-tetramethyl-pyrrolin-3-yl)methyloxy]-9-phenoxy-acridine 5, has been prepared. This key-intermediate reacts with amines to give the corresponding labelled 9-amino substituted...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1998-03, Vol.8 (6), p.669-674
Main Authors: Belmont, Philippe, Chapelle, Christian, Demeunynck, Martine, Michon, Josette, Michon, Pierre, Lhomme, Jean
Format: Article
Language:English
Subjects:
Acridines - metabolism
Antioxidants - metabolism
Biological and medical sciences
Chemistry
DNA - metabolism
DNA-Binding Proteins - metabolism
Electron Spin Resonance Spectroscopy
Exact sciences and technology
Free Radicals
Fundamental and applied biological sciences. Psychology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Interactions. Associations
Intermolecular phenomena
Models, Chemical
Molecular biophysics
Nitrogen Oxides - metabolism
Organic chemistry
Preparations and properties
Spectrometry, Fluorescence
Spin Labels
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Summary:In the search for spin labelled intercalators of general use to construct DNA-binding conjugates, 6-chloro-2-[(1-oxyl-2,2,5,5-tetramethyl-pyrrolin-3-yl)methyloxy]-9-phenoxy-acridine 5, has been prepared. This key-intermediate reacts with amines to give the corresponding labelled 9-amino substituted acridines. Comparative EPR and fluorescence measurements show that the label causes only little modification of the binding properties of acridine. The label causes little modification of the binding properties as shown by comparative fluorescence and EPR studies.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(98)00089-4