title: Structural modeling for DNA binding to antioxidants resveratrol, genistein and curcumin.
abstract: Several models are presented here for the bindings of the antioxidant polyphenols resveratrol, genistein and curcumin with DNA in aqueous solution at physiological conditions. Multiple spectroscopic methods and molecular modeling were used to locate the binding sites of these polyphenols with DNA duplex. Structural models showed that intercalation is more stable for resveratrol and genistein than groove bindings, while curcumin interaction is via DNA grooves. Docking showed more stable complexes formed with resveratrol and genistein than curcumin with the free binding energies of -4.62 for resveratrol-DNA (intercalation), -4.28 for resveratrol-DNA (groove binding), -4.54 for genistein-DNA (intercalation), -4.38 for genistein-DNA (groove binding) and -3.84 kcal/mol for curcumin-DNA (groove binding). The free binding energies show polyphenol-DNA complexation is spontaneous at room temperature. At high polyphenol concentration a major DNA aggregation occurred, while biopolymer remained in B-family structure.
authors.affiliation: Department of Chemistry-Physics, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, Québec G9A 5H7, Canada.
authors.forename: C N
authors.initials: CN
authors.lastname: N'soukpoé-Kossi
authors.affiliation: Department of Chemistry-Physics, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, Québec G9A 5H7, Canada.
authors.forename: P
authors.initials: P
authors.lastname: Bourassa
authors.affiliation: Department of Chemistry-Physics, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, Québec G9A 5H7, Canada.
authors.forename: J S
authors.initials: JS
authors.lastname: Mandeville
authors.affiliation: Department of Chemistry-Physics, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, Québec G9A 5H7, Canada.
authors.forename: L
authors.initials: L
authors.lastname: Bekale
authors.affiliation: Department of Chemistry-Physics, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, Québec G9A 5H7, Canada. Electronic address: tajmirri@uqtr.ca.
authors.forename: H A
authors.initials: HA
authors.lastname: Tajmir-Riahi
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism*; D001665:Binding Sites; D002942:Circular Dichroism; D003474:Curcumin / Q000737:chemistry / Q000378:metabolism*; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D018736:DNA Adducts / Q000737:chemistry / Q000378:metabolism; D019833:Genistein / Q000737:chemistry / Q000378:metabolism*; D007364:Intercalating Agents / Q000737:chemistry / Q000378:metabolism; D008958:Models, Molecular; D062105:Molecular Docking Simulation; D009690:Nucleic Acid Conformation; D000077185:Resveratrol; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013267:Stilbenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000975:Antioxidants; D018736:DNA Adducts; D007364:Intercalating Agents; D013267:Stilbenes; D004247:DNA; D019833:Genistein; D003474:Curcumin; D000077185:Resveratrol
keywords: Conformation; DNA; Intercalation; Modeling; Polyphenols; Stability