Issue 2, 2011
From the journal:

New Journal of Chemistry

3-Substituted xanthines as promising candidates for quadruplex formation: computational, synthetic and analytical studies†

János Szolomájer,a   Gábor Paragi,b   Gyula Batta,c   Célia Fonseca Guerra,d   F. Matthias Bickelhaupt,d   Zoltán Kele,a   Petra Pádár,a   Zoltán Kupihára  and  Lajos Kovács*a  

* Corresponding authors

a Department of Medicinal Chemistry, University of Szeged, Szeged, Hungary
E-mail: kovacs@ovrisc.mdche.u-szeged.hu
Fax: +36 62 545141
Tel: +36 62 545145

b Supramolecular and Nanostructured Materials Research Group of the Hungarian Academy of Sciences, University of Szeged, Szeged, Hungary

c Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary

d Department of Theoretical Chemistry and Amsterdam Center for Multiscale Modeling (ACMM), Scheikundig Laboratorium der Vrije Universteit, Amsterdam, The Netherlands

Abstract

Our computational studies suggest that 3-substituted xanthines are good candidates for tetrad and quadruplex structures. 3-Methylxanthine (3MX) has been synthesized from 7-benzylxanthine, and the existence of tetrameric and octameric aggregates of 3MX with NH4+, Na+ and K+ ions in the gas phase (MS) and in DMSO-d6 solution (NMR) has been observed. The “internal” H-bonds (N1H⋯O6) are stronger than the “external” ones (N7H⋯O2) in these clusters (NMR).

Graphical abstract: 3-Substituted xanthines as promising candidates for quadruplex formation: computational, synthetic and analytical studies

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Article information

DOI
https://doi.org/10.1039/C0NJ00612B
Article type
Paper
Submitted
06 Aug 2010
Accepted
18 Nov 2010
First published
10 Dec 2010

New J. Chem., 2011,35, 476-482

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3-Substituted xanthines as promising candidates for quadruplex formation: computational, synthetic and analytical studies

J. Szolomájer, G. Paragi, G. Batta, C. F. Guerra, F. M. Bickelhaupt, Z. Kele, P. Pádár, Z. Kupihár and L. Kovács, New J. Chem., 2011, 35, 476 DOI: 10.1039/C0NJ00612B

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