title: Spectroscopic, electrochemical DNA binding and in vivo anti-inflammatory studies on newly synthesized Schiff bases of 4-aminophenazone.
abstract: 4-Aminophenazone (Ap-1) Schiff bases i.e., 4-{(3,4,5-trimethoxybenzylidine) amino}phenazone (Ap-2), 4-{(2-chlorobenzylidine) amino}phenazone (Ap-3) and 4-{(4-chlorobenzylidine)amino} phenazone (Ap-4) were synthesized and characterized by different spectroscopic techniques. Interaction of these compounds with ds.DNA was investigated through UV-Visible spectroscopy, fluorescence spectroscopy and cyclic voltammetry at stomach (4.7) and blood (7.4) pH under 37 °C (human body temperature). Instrumental findings were further quantified both kinetically and thermodynamically. Results obtained through these techniques inferred intercalative mode of binding of all the compounds with DNA. The binding constant data, "Kb", and free energy change, ΔG, indicated comparatively greater binding affinity and more spontaneity of binding of compounds with DNA at stomach pH (4.7), respectively. However, among these compounds, Ap-4 showed comparatively greater binding at both the pH. Formation of compound-DNA complex was further confirmed through the decrease in diffusion rates after the addition of DNA. The in vivo anti-inflammatory activity of the compounds was evaluated using the carrageenan-induced hind paw edema method. The results revealed that among all the compounds, Ap-4 showed greater percentage of edema inhibition compared to standard drug.
authors.affiliation: Department of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan. Electronic address: nasimaa2006@yahoo.com.
authors.forename: Nasima
authors.initials: N
authors.lastname: Arshad
authors.affiliation: Department of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan.
authors.forename: Mukhtar
authors.initials: M
authors.lastname: Ahmad
authors.affiliation: Department of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan.
authors.forename: Muhammad Zaman
authors.initials: MZ
authors.lastname: Ashraf
authors.affiliation: Riphah Institutes of Pharmaceutical Sciences, Riphah International University, Islamabad, Pakistan.
authors.forename: Humaira
authors.initials: H
authors.lastname: Nadeem
mesh_terms: D000675:Ampyrone / Q000097:blood / Q000737:chemistry* / Q000627:therapeutic use; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy / Q000473:pathology; D055664:Electrochemical Techniques; D005753:Gastric Mucosa / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D051381:Rats; D017207:Rats, Sprague-Dawley; D012545:Schiff Bases / Q000097:blood / Q000138:chemical synthesis* / Q000627:therapeutic use; D013050:Spectrometry, Fluorescence; D013270:Stomach / Q000187:drug effects; D013696:Temperature; D013816:Thermodynamics
chemical_list: D000893:Anti-Inflammatory Agents; D012545:Schiff Bases; D000675:Ampyrone; D004247:DNA
keywords: 4-Aminophenazone; Anti-inflammatory activity; Cyclic voltammetry; DNA binding interaction; Kinetic and thermodynamic findings; UV–visible/fluorescence spectroscopy