title: Photoisomerizable arylstilbazolium ligands recognize parallel and antiparallel structures of G-quadruplexes.
abstract: The photoisomerization and DNA interaction studies of three arylstilbazolium derivatives with various samples of nucleic acids (duplexes, triplexes and tetraplexes) are reported. The equilibrium dialysis study revealed high binding affinities of ligands to tetraplex structures. The quadruplex-binding affinity could be switched by light, e.g., the E,E and E,Z isomers of 1,4-bis(vinylquinolinium)benzene (1) interacted with parallel and antiparallel tetraplexes exhibiting different binding selectivity. The E,Z-1 showed higher binding preference for c-myc DNA (a propeller-type quadruplex), whereas the E,E-1 favorably interacted with telomeric DNA (a basket-type quadruplex). The presence of quadruplex DNA hampered photoisomerization of quadruplex-bound ligand.
authors: Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland.
authors: Izabella
authors: I
authors: Czerwinska
authors: Bernard
authors: B
authors: Juskowiak
mesh_terms: D001483:Base Sequence; D001597:Benzylidene Compounds / Q000737:chemistry* / Q000378:metabolism*; D004247:DNA / Q000737:chemistry* / Q000235:genetics / Q000378:metabolism*; D054856:G-Quadruplexes; D007536:Isomerism; D008024:Ligands; D008958:Models, Molecular; D055668:Photochemical Processes; D016271:Proto-Oncogene Proteins c-myc / Q000235:genetics; D013379:Substrate Specificity
chemical_list: D001597:Benzylidene Compounds; D008024:Ligands; D016271:Proto-Oncogene Proteins c-myc; D004247:DNA