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Macrocyclic naphthalene diimides as G-quadruplex binders.

Abstract：

:The synthesis, biological and molecular modeling evaluation of a series of macrocyclic naphthalene diimides is reported. The present investigation expands on the study of structure-activity relationships of prototype compound 2 by constraining the molecule into a macrocyclic structure with the aim of improving its G-quadruplex binding activity and selectivity. The new derivatives, compounds 4-7 carry spermidine- and spermine-like linkers while in compound 8 the inner basic nitrogen atoms of spermine have been replaced with oxygen atoms. The design strategy has led to potent compounds stabilizing both human telomeric (F21T) and c-KIT2 quadruplex sequences, and high selectivity for quadruplex in comparison to duplex DNA. Antiproliferative effects of the new derivatives 4-8 have been evaluated in a panel of cancer cell lines and all the tested compounds showed activity in the low micromolar or sub-micromolar range of concentrations. In order to rationalize the molecular basis of the DNA G-quadruplex versus duplex recognition preference, docking and molecular dynamics studies have been performed. The computational results support the observation that the main driving force in the recognition is due to electrostatic factors.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Marchetti C,Minarini A,Tumiatti V,Moraca F,Parrotta L,Alcaro S,Rigo R,Sissi C,Gunaratnam M,Ohnmacht SA,Neidle S,Milelli A

doi

10.1016/j.bmc.2015.03.076

subject

Has Abstract

pub_date

2015-07-01 00:00:00

pages

3819-30

issue

13

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(15)00272-2

journal_volume

23

pub_type

杂志文章

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