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Interaction between double helix DNA fragments and a new topopyrone acting as human topoisomerase I poison.

Abstract：

:A water soluble derivative (2) of topopyrones was selected for NMR studies directed to elucidate the mode of binding with specific oligonucleotides. Topopyrone 2 can intercalate into the CG base pairs, but the residence time into the double helix is very short and a fast chemical exchange averaging occurs at room temperature between the free and bound species. The equilibria involved become slow below room temperature, thus allowing to measure a mean lifetime of the complex of ca. 7 ms at 15 degrees C. Structural models of the complex with d(CGTACG)(2) were developed on the basis of DOSY, 2D NOESY and (31)P NMR experiments. Topopyrone 2 presents a strong tendency to self-associate. In the presence of oligonucleotide a certain number of ligand molecules are found to externally stack to the double-helix, in addition to a small fraction of the same ligand intercalated. The external binding to the ionic surface of the phosphoribose chains may thus represents the first step of the intercalation process.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Scaglioni L,Mazzini S,Mondelli R,Dallavalle S,Gattinoni S,Tinelli S,Beretta GL,Zunino F,Ragg E

doi

10.1016/j.bmc.2008.12.005

subject

Has Abstract

pub_date

2009-01-15 00:00:00

pages

484-91

issue

2

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)01171-1

journal_volume

17

pub_type

杂志文章

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