Structural flexibilityversusrigidity of the aromatic unit of DNA ligands: binding of aza- and azoniastilbene derivatives to duplex and quadruplex DNA

Abstract

The increased flexibility of a quadruplex-DNA ligand does not necessarily lead to stronger interactions with the quadruplex DNA as compared with rigid ligands that have essentially the same size and extent of π system.

Bis(phenylethynyl)arene Linkers in Tetracationic Bis‐triarylborane Chromophores Control Fluorimetric and Raman Sensing of Various DNAs and RNAs

“…Detailed investigation of these bio‐macromolecules and understanding of the interactions that influence their communication on a molecular level is a broad and interdisciplinary research field. One well‐established way to approach the subject is to study the interactions and binding behaviours of small molecules with DNA and RNA [6–17] …”

“…One well-established way to approach the subjecti st os tudy the interactions andb inding behaviours of small molecules with DNA and RNA. [6][7][8][9][10][11][12][13][14][15][16][17] There are three main binding modes, namely intercalation, groove binding and external binding (Figure 1). [22,23] For intercalation to occur,t he helical structureo ft he bio-macromole-cule needs to unwind to allow for as mall molecule to insert in between the coplanarly arranged nucleobases.…”

Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2 + 2] cycloaddition and cycloreversion

“…As the quinolizinium ion has been established as a versatile platform for the development of DNA intercalators [60], we identified styryl-substituted quinolizinium derivatives as a promising basis for the search for photoswitchable DNA binders based on the photocycloaddition-photocycloreversion equilibrium. In fact, some selected styrylquinolizinium derivatives have already been shown to bind to DNA [61][62][63][64][65][66][67], however, their photocycloaddition reaction and the propensity of the corresponding photodimers to release the DNA-binding ligand have not been reported so far. Herein, we report on the photochemical and DNA-binding properties of the selected styrylquinolizinium derivatives 3a-d and demonstrate their ability to operate as photoswitchable DNA ligands.…”

Flexible RuII Schiff Base Complexes: G‐Quadruplex DNA Binding and Photo‐Induced Cancer Cell Death

“…[37][38][39] More recently,studies focusedo n the importance of designing more flexible ligands for recogniz-ing G4 over duplex DNA thanks to favored groove interactions. [40,41] In the presentp aper,w ew ere interested in studying new kinds of Ru II complexes that do not contain ar igidp olyazaaromatic interacting ligand but am ore flexible interacting ligand with av iew of enhancing the selectivity for G4 over duplex DNA. Ru II compounds carrying Schiff base type ligand 1-4 were chosen for their high structuralv ersatility as well as for their interacting part flexibility (Figure 1).…”

“…The high affinity of these compounds mainly arises from efficient π ‐stacking interactions with the G4 external quartet and additional interaction with the G4 grooves also appeared to play a prominent role in the interaction of some complexes [37–39] . More recently, studies focused on the importance of designing more flexible ligands for recognizing G4 over duplex DNA thanks to favored groove interactions [40, 41] …”