title: Zwitterionic pyrimidinium adducts as antioxidants with therapeutic potential as nitric oxide scavenger.
abstract: A variety of zwitterionic adducts were synthesized by using means green chemistry method. The products contain the biologically active barbituric acid moiety embedded in zwitterion products. Both features are pharmaceutically relevant. The chemical structures were deduced by (1)H-, (13)C-, NMR and HRMS spectral analysis, and X-ray diffraction techniques. In vitro evaluation for the antioxidant activities were carried out towards the inhibition of nitric oxide (NO) radical, known to regulate a mechanism of signals for various cellular functions. NO also play an important role as a mediator of various pathological conditions responsible for cellular damages such as strokes, cancers, diabetes, chronic heart failure and inflammatory disease and various neurodegenerative disorders. All tested compounds were found to be more potent nitric oxide scavengers as compared to standard drug ascorbic acid (IC50 = 618 ± 2.0 μM). Compounds 4c and e exhibiting several hundred fold more activity against nitric oxide radical with IC50 values of 69 ± 1.66 and 70.1 ± 0.89 μM respectively, as compared to standard drug ascorbic acid (IC50 = 618 ± 2.0 μM).
authors.affiliation: Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia; Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt. Electronic address: ambarakat@ksu.edu.sa.
authors.forename: Assem
authors.initials: A
authors.lastname: Barakat
authors.affiliation: Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia.
authors.forename: Abdullah Mohammed
authors.initials: AM
authors.lastname: Al-Majid
authors.affiliation: Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia.
authors.forename: Hany J
authors.initials: HJ
authors.lastname: Al-Najjar
authors.affiliation: Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia.
authors.forename: Yahia Nasser
authors.initials: YN
authors.lastname: Mabkhot
authors.affiliation: H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, Pakistan.
authors.forename: Sumaira
authors.initials: S
authors.lastname: Javaid
authors.affiliation: H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, Pakistan.
authors.forename: Sammer
authors.initials: S
authors.lastname: Yousuf
authors.affiliation: Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia; H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, Pakistan.
authors.forename: M Iqbal
authors.initials: MI
authors.lastname: Choudhary
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005609:Free Radicals / Q000037:antagonists & inhibitors / Q000378:metabolism; D008958:Models, Molecular; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000378:metabolism; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000975:Antioxidants; D016166:Free Radical Scavengers; D005609:Free Radicals; D011743:Pyrimidines; D009569:Nitric Oxide
keywords: Barbituric acids; Cancer; Chronic inflammatory disease and heart failure; Diabetes; Nitric oxide (NO); Reactive oxygen species (ROS); Zwitterion