Click Modification of Diazido Acridine Intercalators: A Versatile Route towards Decorated DNA Nanostructures

Abstract

Diazido derivatives of 3,6-diamino acridine (proflavine) intercalate into DNA and undergo functionalization through click chemistry to form 1D nanostructures with redox active, conductive nanowire, and fluorescent properties. This two-step approach, intercalation followed by click modification allows for the controlled decoration of DNA nanostructures.

Thermoresponsive DNA by Intercalation of dsDNA with Oligoethylene‐Glycol‐Functionalized Small‐Molecule Intercalators

“…The synthesized intercalators display a strong absorption in the UV–vis region (around 381 nm), as generally observed for Pf based intercalators . The intercalation of the four synthesized OEG‐functionalized intercalators with dsDNA was studied by UV–vis spectroscopy.…”

“…In this work, we aimed to develop intrinsically thermoresponsive dsDNA constructs by intercalating a small molecule modified with oligoethylene glycol chains. As an easy modification route and successful intercalation with dsDNA have been previously reported, proflavine (Pf) (3,6‐diaminoacridine)‐based intercalators were selected . The introduction of oligoethylene glycol side chains is a general strategy to equip polymers with LCST behavior, albeit these are commonly based on covalent constructs.…”

“…In contrast, all solutions of the intercalator‐dsDNA complexes were stable in pure 5 m m sodium phosphate buffer, even with the most hydrophobic intercalator MeMEG‐Pf (Figure S19B, Supporting Information) (detailed procedure for the preparation of dsDNA‐intercalator complex is described in the Supporting Information. In each case the intercalator versus DNA base pair ratio was kept constant, 1:2, as previously described for proflavine based intercalators). The high water solubility of the dsDNA helps to improve the solution stability of all the OEG‐intercalator conjugates, which indirectly confirms the successful intercalation of all the intercalators into the dsDNA.…”

Combination of photodynamic therapy and gene silencing achieved through the hierarchical self-assembly of porphyrin-siRNA complexes

“…Porphyrin can self-associate into supramolecular polymers, [20] but cationic porphyrins are also known to be excellent DNA ligands. [27] Generally speaking, DNA binding can occur according to three different modes (intercalation, [28,29] groove binding, [30,31] external binding [23,24] ) and all of them have been reported with cationic porphyrins of different structures varying the position and size of their substituents, and the nature, number and position of positive charges. [27,[32][33][34] Wishing to explore the specific mode of binding of H2-PG, we studied its interaction with different types of DNA, single-and double-stranded, by UV-Vis, fluorescence, and circular dichroism spectroscopies.…”