Selective G-quadruplex stabilizers: Schiff-base metal complexes with anticancer activity

Terenzi, Alessio; Bonsignore, Riccardo; Spinello, Angelo; Gentile, Carla; Martorana, Annamaria; Ducani, Cosimo; Högberg, Björn; Almerico, Anna Maria; Lauria, Antonino; Barone, Giampaolo

doi:10.1039/c4ra05355a

Cited by 91 publications

(82 citation statements)

References 80 publications

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“…[14,15] An example of this, are metal salphen ands alen complexes, which have been extensively studied over the past 10 years (see Figure 1). [16,17] Aw ide range of derivatives with different metals (and hence geometries), [18][19][20] salphen/salen core structure [21,22] and nature/number/position of substituents [19,[23][24][25][26][27] have been reporteda se xcellent G4 DNA binders. In spite of this, there is still little information regardingt he selectivity of metal-salphens against several different G4 DNA structures.…”

Section: Introductionmentioning

confidence: 99%

Binding Studies of Metal–Salphen and Metal–Bipyridine Complexes towards G‐Quadruplex DNA

Łęczkowska

González‐García

Pérez‐Arnaiz

et al. 2018

Chemistry A European J

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The proposed in vivo formation of G-quadruplex DNA (G4 DNA) in promoter regions of oncogenes and in telomeres has prompted the development of small molecules with high affinity and selectivity for these structures. Herein we report the synthesis of a new di-substituted bipyridine ligand and the corresponding complexes with Ni and VO . Both these new complexes have been characterized spectroscopically and by X-ray crystallography. Detailed DNA binding studies of these two complexes, together with three previously reported metal salphen complexes, are presented. Using FRET melting assays, the binding affinity and selectivity of the five metal complexes against six different G4 DNA structures as well as a duplex DNA have been determined. In addition, we present detailed ITC and UV/Vis studies to characterize the interaction of the complexes with human telomeric G4 DNA. Finally, we show via a polymerase stop assay that these complexes are able to stabilize a G4 DNA structure (from the c-Myc oncogene promoter) and halt the activity of Taq polymerase.

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Section: Introductionmentioning

confidence: 99%

Binding Studies of Metal–Salphen and Metal–Bipyridine Complexes towards G‐Quadruplex DNA

Łęczkowska

González‐García

Pérez‐Arnaiz

et al. 2018

Chemistry A European J

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“…The interaction with the G‐quadruplex grooves and loops is also taken into account for improving the selectivity for G‐quadruplex versus duplex DNA. Among the compounds able to target G‐quadruplexes, a number of metal complexes bearing aromatic ligands have been reported, including those of porphyrin, salphens, and salophens . In this context, we have designed a new extended planar ligand, based on a pyrazine core, namely dipyrazino[2,3‐ a :2′,3′‐ h ]phenazine (dph; Figure a).…”

Section: Introductionmentioning

confidence: 99%

New Ruthenium‐Based Probes for Selective G‐Quadruplex Targeting

Piraux

Bar

Abraham

et al. 2017

Chemistry A European J

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Telomeric regions containing G-quadruplex (G4) structures play a pivotal role in the development of cancers. The development of specific binders for G4s is thus of great interest in order to gain a deeper understanding of the role of these structures, and to ultimately develop new anticancer drug candidates. For several years, Ru complexes have been studied as efficient probes for DNA. Interest in these complexes stems mainly from the tunability of their structures and properties, and the possibility of using light excitation as a tool to probe their environment or to selectively trigger their reaction with a biological target. Herein, we report on the synthesis and thorough study of new Ru complexes based on a novel dipyrazino[2,3-a:2',3'-h]phenazine ligand (dph), obtained through a Chichibabin-like reaction. Luminescence experiments, surface plasmon resonance (SPR), and computational studies have demonstrated that these complexes behave as selective probes for G-quadruplex structures.

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“…They show potential applications and properties such as anticancer, anticonvulsant, antitumor, antifungal, antibacterial, antitubercular, antioxidant, antimalarial, anti-inflammatory and anti-HIV activities [5,[18][19][20][21][22][23][24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, X-ray crystal structures and antibacterial activities of Schiff base ligands derived from allylamine and their vanadium(IV), cobalt(III), nickel(II), copper(II), zinc(II) and palladium(II) complexes

Rudbari

Iravani

Moazam

et al. 2016

Journal of Molecular Structure

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Selective G-quadruplex stabilizers: Schiff-base metal complexes with anticancer activity

Abstract: Molecular dynamics simulations and quantum mechanics/molecular mechanics calculations provided a mechanism for G-quadruplex binding of three transition metal complexes.

Cited by 91 publications

References 80 publications

Binding Studies of Metal–Salphen and Metal–Bipyridine Complexes towards G‐Quadruplex DNA

Binding Studies of Metal–Salphen and Metal–Bipyridine Complexes towards G‐Quadruplex DNA

New Ruthenium‐Based Probes for Selective G‐Quadruplex Targeting

Synthesis, characterization, X-ray crystal structures and antibacterial activities of Schiff base ligands derived from allylamine and their vanadium(IV), cobalt(III), nickel(II), copper(II), zinc(II) and palladium(II) complexes

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