Phthalocyanines: a new class of G-quadruplex-ligands with many potential applications

Abstract

A G-quadruplex is a four-stranded DNA structure featuring stacked guanine tetrads, G-quartets. Formation of a G-quadruplex in telomere DNA can inhibit telomerase activity; therefore, development of G-quadruplex-ligands, which induce and/or stabilize G-quadruplexes, has become an area of great interest. Phthalocyanine derivatives have substantial potential as high-affinity G-quadruplex-ligands because these planar chromophores are similar in size and shape to the G-quartets. Here, we focus on the latest findings on phthalocyanine derivatives as G-quadruplex-ligands, and discuss the mechanisms by which phthalocyanines bind to G-quadruplexes with high affinity and selectivity. We also discuss potential biomedical and organic electronic applications of phthalocyanines that are dependent on their photophysical properties.

Porphyrins in complex with DNA: Modes of interaction and oxidation reactions

“…It is striking to note that negatively charged compounds such as Nmethylmesoporphyrin IX (NMM) [44,45,132,133], protoporphyrin IX [134], hemin (Fe IIIprotoporphyrin IX) [135][136][137] with two carboxylic groups or tetraphtalocyanines with four sulfonate groups [138][139][140] are endowed with G-quadruplex binding capability. Since negatively charged molecules are devoid of any affinity for double-stranded DNA due to strong electrostatic repulsion, negatively charged aromatic molecules that are able to undergo external stacking with a G-quartet have a chance to be G-quadruplex selective [138,140].…”

Binding Modes and Selectivity of Ruthenium Complexes to Human Telomeric DNA G‐Quadruplexes

“…The search for new molecules able to stabilize G4s has become an active field of research in anti‐cancer drug design . This includes notably planar π‐conjugated molecules, porphyrins and phthalocyanine derivatives, and coordination complexes . It has been demonstrated that coordination complexes (e.g., with Ru II , Ni II , Zn II , Mn III metal centers) can strongly and selectively interact with DNA G4 .…”

Mutual influence between contiguous TMPyP4 ligands when bound to a synthetic double-stranded Poly(A)-Poly(U)

“…To understand how these ligands actually influence on dsDNA, RNA and other forms of DNA functions, in particular highly ordered structures that may be formed by the folded DNA chain has also essential application in chemical biology and medicinal chemistry [3,4]. The nonspecific binding makes difficult for drugs applications related to folded DNA because dsDNA coexist and could prevent the interaction between ligand and target structure [5,6]. The specificity of a ligand may be evaluated from the comparison of affinity to a site and cooperativity during binding of a ligand to the DNA oligomer vs. the DNA polymer [7].…”