title: Synthesis, characterization, biological screenings and interaction with calf thymus DNA of a novel azomethine 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol.
abstract: The novel azomethine, 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol (HL) was synthesized and characterized by elemental analysis, FT-IR, (1)H, (13)C NMR spectroscopy and single crystal analysis. The title compound has been screened for its biological activities including enzymatic study, antibacterial, antifungal, cytotoxicity, antioxidant and interaction with CTDNA, and showed remarkable activities in each area of research. The titled compound interacts with DNA via two binding modes: intercalation and groove binding. In intercalation the compound inserts itself into the base pairs of DNA and the compound-DNA complex is stabilized by π-π stacking. Interaction via groove binding may be due to hydrogen bonding to bases, typically to N3 of adenine and O2 of thymine. The synthesized compound was also found to be an effective antioxidant of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and gives percent inhibition (%I) of 90.7 at a concentration level of 31.3μg/mL.
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Sirajuddin
authors.forename: Saqib
authors.initials: S
authors.lastname: Ali
authors.forename: Naseer Ali
authors.initials: NA
authors.lastname: Shah
authors.forename: Muhammad Rashid
authors.initials: MR
authors.lastname: Khan
authors.forename: Muhammad Nawaz
authors.initials: MN
authors.lastname: Tahir
mesh_terms: D000042:Absorption / Q000187:drug effects; D000818:Animals; D000900:Anti-Bacterial Agents / Q000494:pharmacology; D000935:Antifungal Agents / Q000494:pharmacology; D001156:Artemia / Q000166:cytology / Q000187:drug effects; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000378:metabolism; D016923:Cell Death / Q000187:drug effects; D003217:Conductometry; D018360:Crystallography, X-Ray; D004247:DNA / Q000378:metabolism*; D055664:Electrochemical Techniques; D016166:Free Radical Scavengers / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D010851:Picrates / Q000378:metabolism; D013055:Spectrophotometry, Infrared; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D014783:Viscosity / Q000187:drug effects
chemical_list: C575200:3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001391:Azo Compounds; D001555:Benzene Derivatives; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D007097:Imines; D008024:Ligands; D010851:Picrates; D013882:Thiosemicarbazones; C512188:azomethine; D004247:DNA; C427203:calf thymus DNA; C004931:1,1-diphenyl-2-picrylhydrazyl