A Modular Synthetic
Route to Dimeric Calixarenes: A New Family of DNA Major Groove Binders

C. J. Blecking; W. Hu; R. Zadmard; A. Dasgupta; T. Schrader

doi:10.1055/s-0030-1259980

FEATUREARTICLE

A Modular Synthetic Route to Dimeric Calixarenes: A New Family of DNA Major Groove Binders

C. J. Blecking^a, W. Hu^a, R. Zadmard^b, A. Dasgupta^a, T. Schrader*^a
^a Department of Chemistry, University of Duisburg-Essen, Universitätsstr. 5, 45117 Essen, Germany
Fax: +49(201)1834252; e-Mail: thomas.schrader@uni-due.de;
^b Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran

Abstract

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Abstract

We describe here a general strategy for the synthesis of dimeric anilinium/guanidinium calix[4]arenes with aliphatic and heteroaromatic bridges. These compounds display a remarkably high affinity towards double-stranded (ds) DNA and act by a rare mechanism, i.e., insertion into the wide major groove of the nucleic acids.

Key words

DNA - major groove - sequence selectivity - binding affinity - calixarenes - oligopyrroles

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