title: Interaction of glycyrrhizin and glycyrrhetinic acid with DNA.
abstract: Glycyrrhizin (GL), a molecule of glycyrrhetinic acid (GA), is an aqueous extract from licorice root. These compounds are well known for their anti-inflammatory, hepatocarcinogenesis, antiviral, and interferon-inducing activities. This study is the first attempt to investigate the binding of GL and GA with DNA. The effect of ligand complexation on DNA aggregation and condensation was investigated in aqueous solution at physiological conditions, using constant DNA concentration (6.25 mM) and various ligands/polynucleotide (phosphate) ratios of 1/240, 1/120, 1/80, 1/40, 1/20, 1/10, 1/5, 1/2, and 1/1. Fourier transform infrared and ultraviolet (UV)-visible spectroscopic methods were used to determine the ligand binding modes, the binding constants, and the stability of ligand-DNA complexes in aqueous solution. Spectroscopic evidence showed that GL and GA bind DNA via major and minor grooves as well as the backbone phosphate group with overall binding constants of K(GL-DNA)=5.7×10(3) M(-1), K(GA-DNA)=5.1×10(3) M(-1). The affinity of ligand-DNA binding is in the order of GL>GA. DNA remained in the B-family structure, whereas biopolymer aggregation occurred at high triterpenoid concentrations.
authors.affiliation: Department of Chemistry, Islamic Azad University-Central Tehran Branch, Tehran, Iran. drsnafisi@yahoo.com
authors.forename: Shohreh
authors.initials: S
authors.lastname: Nafisi
authors.forename: Mahyar
authors.initials: M
authors.lastname: Bonsaii
authors.forename: Firouzeh
authors.initials: F
authors.lastname: Manouchehri
authors.forename: Khosrou
authors.initials: K
authors.lastname: Abdi
mesh_terms: D000465:Algorithms; D000818:Animals; D001665:Binding Sites; D002417:Cattle; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D018736:DNA Adducts / Q000737:chemistry*; D006034:Glycyrrhetinic Acid / Q000737:chemistry* / Q000378:metabolism; D006035:Glycyrrhiza / Q000737:chemistry; D019695:Glycyrrhizic Acid / Q000737:chemistry* / Q000378:metabolism; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D013053:Spectrophotometry; D017550:Spectroscopy, Fourier Transform Infrared; D013816:Thermodynamics
chemical_list: D018736:DNA Adducts; D019695:Glycyrrhizic Acid; D004247:DNA; C427203:calf thymus DNA; D006034:Glycyrrhetinic Acid