Synthesis via A3 Coupling Reaction of Anthracene‐Propargylamine as a New Scaffold for the Interaction with DNA

Abstract

A series of new anthracene‐propargylamine derivatives were obtained through an efficient synthesis based on the A3 coupling reaction. This set of planar molecules were designed to bind double stranded and G‐quadruplex DNA arrangements. Their interaction pattern of the small molecules with DNA was predicted by molecular docking and their theoretical pharmacokinetic properties were calculated, giving encouraging results in terms of drug‐likeness. The general preference for double stranded DNA suggested by docking experiments was supported by a set of electrospray ionization mass spectrometry (ESI‐MS) experiments.

Combining Electrospray Mass Spectrometry (ESI-MS) and Computational Techniques in the Assessment of G-Quadruplex Ligands: A Hybrid Approach to Optimize Hit Discovery

“…In fact, it is not uncommon to observe overlaps between signals at higher charge states. 100 More in general, high-resolution instruments facilitate the assignment of the charge of a peak from the isotopic distribution ( Figure 2 ). 28 …”

“…On the other hand, and using a similar approach, competition experiments using mixtures of several ligands can be performed. 100 , 108 …”

“…This is desirable, particularly when carrying out a competition assay between compounds generating ligand–GQ complexes with similar molecular weights. In fact, it is not uncommon to observe overlaps between signals at higher charge states . More in general, high-resolution instruments facilitate the assignment of the charge of a peak from the isotopic distribution (Figure ).…”

Synthesis, characterization and anticancer evaluation of nitrogen-substituted 1-(3-aminoprop-1-ynyl)-4-hydroxyanthraquinone derivatives

“…Small molecules with a anthraquinone core [47] and hetaryl fused anthracene-9,10-diones [48] were able to interact with G-quadruplexes and capable of forming four-strand structures. Recently, the anthracene-9-propargylamine scaffold was characterized as a new G-quadruplex ligand [49].…”

Amino‐Acid‐Anthraquinone Click Chemistry Conjugates Selectively Target Human Telomeric G‐Quadruplexes

“…Different G4 stabilizing molecules such as anthraquinones (AQs), [6–8] porphyrins, perylenes, [9] acridines, anthracenes, [10,11] xanthones, [12,13] and also natural compounds [14–17] have been shown to inhibit the telomere elongation operated by telomerase, and several other derivatives are under investigation as potential anticancer drugs. AQs are well‐known nucleic acids ligands [6,8] .…”