title: Synthesis, characterization and biological evaluation of novel α, β unsaturated amides.
abstract: Three derivatives of α,β unsaturated amides have been successfully synthesized via Ugi-four component (U-4CR) reaction. The interactions of the amides with calf thymus deoxyribonucleic acid (ct-DNA) have been investigated in the Tris-HCl buffer (pH=7.4) using viscometric, spectroscopic, thermal denaturation studies, and also molecular docking. By UV-Vis absorption spectroscopy studies, adding CT-DNA to the compound solution caused the hypochromism indicates that there are interactions between the compounds and DNA base pairs. In competitive fluorescence with methylene blue as an intercalator probe, adding compounds to DNA-MB solution caused an increase in emission spectra of the complex. This could be because of compound replacing, with similar binding mode of MB, between the DNA base pairs due to release of bonded MB molecules from DNA-MB complex. Thermal denaturation studies and viscometric experiments also indicated that all three investigated compounds bind to CT-DNA by non-classical intercalation mode. Additionally, molecular docking technique predicted partial intercalation binding mode for the compounds. Also, the highest binding energy was obtained for compound 5a. These results are in agreement with results obtained by empirical methods.
authors.affiliation: Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran.
authors.forename: K
authors.initials: K
authors.lastname: Esmailzadeh
authors.affiliation: Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran; Research and Technology Center of Biomolecules, Ferdowsi University of Mashhad, Mashhad, Iran. Electronic address: housain@um.ac.ir.
authors.forename: M R
authors.initials: MR
authors.lastname: Housaindokht
authors.affiliation: Department of Chemistry, Faculty of Science, University of Birjand, Birjand, Iran.
authors.forename: A
authors.initials: A
authors.lastname: Moradi
authors.affiliation: Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran; Research and Technology Center of Biomolecules, Ferdowsi University of Mashhad, Mashhad, Iran.
authors.forename: A A
authors.initials: AA
authors.lastname: Esmaeili
authors.affiliation: Research and Technology Center of Biomolecules, Ferdowsi University of Mashhad, Mashhad, Iran.
authors.forename: Z
authors.initials: Z
authors.lastname: Sharifi
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D002417:Cattle; D002942:Circular Dichroism; D004247:DNA / Q000378:metabolism*; D007364:Intercalating Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D062105:Molecular Docking Simulation; D013816:Thermodynamics
chemical_list: D000577:Amides; D007364:Intercalating Agents; D004247:DNA; C427203:calf thymus DNA
keywords: Calf thymus DNA; Intercalator; Molecular docking; Spectroscopy; Synthesis