Issue 3, 2004

Effects of an 8-bromodeoxyguanosine incorporation on the parallel quadruplex structure [d(TGGGT)]4

Abstract

NMR, molecular dynamics and mechanics calculations, and CD spectroscopy were used to characterise three tetramolecular quadruplex complexes: [d(TGBrGGT)]4, [d(TGGBrGT)]4 and [d(TGGGBrT)]4, where GBr indicates an 8-bromoguanine residue. All three quadruplexes are characterised by a 4-fold symmetry with all strands parallel to each other and, differently to what has been observed for other parallel quadruplex structures, with a tetrad (formed by 8-Br-dGs) in a syn conformation. The whole of the data demonstrates that the replacement in turn of different dG residues with 8-Br-dG in the sequence 5′-TGGGT-3′ affects the resulting structures in different ways, leading to different CD profiles and thermal stabilities. Particularly, [d(TGBrGGT)]4 and [d(TGGBrGT)]4 are more stable than the unmodified sequence, whereas [d(TGGGBrT)]4 is much less stable than the natural counterpart. The conformational features found in the three quadruplexes might, in principle, amplify the range of applicability of synthetic oligonucleotides as aptamers or catalysts, by providing novel structural motifs with different molecular recognition capabilities from those of native DNA sequences.

Graphical abstract: Effects of an 8-bromodeoxyguanosine incorporation on the parallel quadruplex structure [d(TGGGT)]4

Article information

Article type
Paper
Submitted
14 Nov 2003
Accepted
10 Dec 2003
First published
12 Jan 2004

Org. Biomol. Chem., 2004,2, 313-318

Effects of an 8-bromodeoxyguanosine incorporation on the parallel quadruplex structure [d(TGGGT)]4

V. Esposito, A. Randazzo, G. Piccialli, L. Petraccone, C. Giancola and L. Mayol, Org. Biomol. Chem., 2004, 2, 313 DOI: 10.1039/B314672C

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