title: Spectroscopic, molecular modeling, and NMR-spectroscopic investigation of the binding mode of the natural alkaloids berberine and sanguinarine to human telomeric G-quadruplex DNA.
abstract: G-quadruplex structures can be formed at the single-stranded overhang of telomeric DNA, and ligands able to stabilize this structure have recently been identified as potential anticancer drugs. Among the potential G-quadruplex binders, we have studied the binding ability of berberine and sanguinarine, two members of the alkaloid family, an important class of natural products long known for medicinal purpose. Our spectroscopic (CD, NMR, and fluorescence) studies and molecular modeling approaches revealed binding modes at ligand-complex stoichiometries >1:1 and ligand self-association induced by DNA for the interactions of the natural alkaloids berberine and sanguinarine with the human telomeric G-quadruplex DNA.
authors.affiliation: Department of Pharmaceutical Sciences, University of Firenze, Via Ugo Schiff 6, I-50019 Sesto Fiorentino, Firenze, Italy.
authors.forename: Irene
authors.initials: I
authors.lastname: Bessi
authors.forename: Carla
authors.initials: C
authors.lastname: Bazzicalupi
authors.forename: Christian
authors.initials: C
authors.lastname: Richter
authors.forename: Hendrik R A
authors.initials: HR
authors.lastname: Jonker
authors.forename: Krishna
authors.initials: K
authors.lastname: Saxena
authors.forename: Claudia
authors.initials: C
authors.lastname: Sissi
authors.forename: Matteo
authors.initials: M
authors.lastname: Chioccioli
authors.forename: Sara
authors.initials: S
authors.lastname: Bianco
authors.forename: Anna Rita
authors.initials: AR
authors.lastname: Bilia
authors.forename: Harald
authors.initials: H
authors.lastname: Schwalbe
authors.forename: Paola
authors.initials: P
authors.lastname: Gratteri
mesh_terms: D053119:Benzophenanthridines / Q000494:pharmacology*; D001599:Berberine / Q000494:pharmacology*; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry*; D054856:G-Quadruplexes / Q000187:drug effects*; D006801:Humans; D007546:Isoquinolines / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013050:Spectrometry, Fluorescence
chemical_list: D053119:Benzophenanthridines; D007546:Isoquinolines; D001599:Berberine; D004247:DNA; C005705:sanguinarine