937
Views
5
CrossRef citations to date
0
Altmetric
Articles

Thermodynamics-antioxidant activity relationships of some 4-benzylidenamino-4, 5-dihydro-1h-1,2,4-triazol-5-one derivatives: Theoretical evaluation

, , , , , & show all
Pages 1935-1948 | Received 23 May 2016, Accepted 13 Aug 2016, Published online: 19 Jan 2017

References

  • Krystona, T.B.; Georgieva, A.B.; Pissis, P.; Georgakilasa, A.G. Role of Oxidative Stress and DNA Damage in Human Carcinogenesis. Mutation Research/Fundamental and Molecular Mechanism of Mutagenesis 2011, 711, 193–201.
  • Jiranusornkul, S.; Laughton, C.A. Destabilization of DNA Duplexes by Oxidative Damage at Guanine: Implications for Lesion Recognition and Repair. Journal of the Royal Society Interface 2008, 5, 191–198.
  • Konsta, A.A.; Visvardis, E.E.; Haveles, K.S.; Georgakilas, A.G.; Sideris. E.G. Detecting Radiation-Induced DNA Damage: From Changes in Dielectric Properties to Programmed Cell Death. Journal of Non-Crystalline Solids 2003, 305, 295–302.
  • Spassky, A.; Angelov, D. Influence of the Local Helical Conformation on the Guanine Modifications Generated from One-Electron DNA Oxidation. Biochemistry 1997, 36, 6571–6576.
  • Gillard, N.; Begusova, M.; Castaing, B.; Potheim-Maurizot, M. Radiation Effects Binding of Fgp Repair Protein to An Abasic Site Containing DNA. Radiation Research 2004, 162, 566–571.
  • Boveris, A. Superoxide Radical and Hydrogen Peroxide in Mitochondria. Free Radicals in Biology; Pryor, W.A.; Ed.; Academic Press: New York, NY, 1982; 65–89.
  • Misra, H.P.; Fridovich, I. The Role of Superoxide Anion in the Autooxidation of Epinephrine and a Simple Assay for Superoxide Dismutase. Journal of Biological Chemistry 1972, 247, 3170–3175.
  • Levine, S.A.; Kidd, P.M. Antioxidant Adaptation: A Unified Disease Theory. Journal of Orthomolecular Psychiatry 1983, 14, 19–38.
  • Cuzzocrea, S.; Riley, D.P.; Caputi, A.P.; Salvemini, D. Antioxidant Therapy: A New Pharmacological Approach in Shock, Inflammation, and Ischemia/Reperfusion Injury. The American Society for Pharmacology and Experimental 2001, 53, 135–159.
  • Gilgun-Sherki, Y.; Rosenbaum, Z.; Melamed, E.; Offen, D. Antioxidant Therapy in Acute Central Nervous System Injury: Current State. Pharmacological Reviews 2002, 54, 271–284.
  • Kirkham, P.; Rahman, I. Oxidative Stress in Asthma and COPD: Antioxidants As a Therapeutic Strategy. Pharmacology and Therapeutics 2006, 111, 476–494.
  • Winkler, C.; Frick, B.; Schroecksnadelm, K.; Schennach, H.; Fuchs, D. Food Preservatives Sodium Sulfite and Sorbic Acid Suppress Mitogen-Stimulated Peripheral Blood Mononuclear Cells. Journal of Food and Chemical Toxicology 2006, 44, 2003–2007.
  • Lupo, M.P. Antioxidants and Vitamins in Cosmetics. Journal of Clinical Dermatatology 2001, 19, 467–473.
  • Merken, H.M.; Beecher, G.R. Measurement of Food Flavonoids by High-Performance Liquid Chromatography. Journal of Agricultural and Food Chemistry 2000, 48, 578–599.
  • Kawaii, S.; Tomono, Y.; Katase, E.; Ogawa, K.; Yano, M. Antiproliferative Effects of Readily Extractable Fraction Prepared from Citrius Juices on Several Cancer Cell Lines. Journal of Agricultural and Food Chemistry 1999, 47, 2509–2512.
  • Manthey, J.A.; Guthrie, N. Antiproliferative Activities of Citrius Flavonoids Against Six Cancer Cell Lines. Journal of Agricultural and Food Chemistry 2002, 50, 5837–5843.
  • Kuhnau, J. The Flavonoids. A Class of Semi-Essential Food Components: Their Role in Human Nutrition. World Review of Nutrition and Dietetics 1976, 24, 117–191.
  • Manach, C.; Scalbert, A.; Morand, C.; Remesy, C.; Jimenez, L. Polyphenols: Food Sources and Bioavailability. The American Journal of Clinical Nutrition 2004, 79, 727–747.
  • Manach, C.; Williamson, G.; Morand, C.; Scalbert, A.; Remesy, C. Bioavailability and Bioefficacy of Polyphenols in Humans. American Journal of Clinical Nutrition 2005, 81, S230–S242.
  • Wright, J.S.; Johnson, E.R.; DiLabio, G.A. Predicting the Antioxidant Activity of Phenolic Antioxidant: Theoretical Method, Analysis of Substituent Effects, and Application to Major Families of Antioxidants. Journal of the American Chemical Society 2001, 123, 1173–1183.
  • Yunsheng, X.; Youguang, Z.; Lin, A.; Yunyan, D.;Yi, L. Density Functional Theory of the Structure-Antioxidant Activity of Polyphenolic Deoxybenzoins. Journal of Food Chemistry 2014, 151, 198–206.
  • Javan, A.J.; Javan, M.J.; Tehrani, A.A. Theoretical Investigation on Antioxidant Activity of Bromophenol from the Marine Red Alga Rhodomela Confervoides: H-Atom Versus Electron Tranfer Mechanism. Journal of Agricultural and Food Chemistry 2013, 61, 1534–1541.
  • Fifen, J.J.; Nsangou, M.; Dhaouadi, N.; Motapon, O.; Jaidane, N. Solvent Effects on the Antioxidant Activity of 3,4-Dihydroxyphenylpyruvic Acid: DFT and TD-DFT Studies. Journal of Computional Chemistry 2011, 966, 232–243.
  • Leopoldini, M.; Russo, N.; Toscano, M. Iron Chelation by the Powerful Antioxidant Flavonoid Quercetin. Journal of Agricultural and Food Chemistry 2006, 54, 3078–3085.
  • Leopoldini, M.; Russo, N.; Toscano, M. The Molecular Basis of Working Mechanism of Natural Polyphenolic Antioxidants. Food Chemistry 2011, 125, 288–306.
  • Mezsam, N. On the Antioxidant Activity of the Ortho and Meta Substituted Daidzein Derivatives in the Gas Phase and Solvent Environment. Journal of the Mexican Chemical Society 2014, 58, 36–45.
  • Holtomo, O.; Nsangou, M.; Fifen, J.J.; Motapon, O. Antioxidative Potency and UV-Vis Spectra of the Compounds Resulting from the Chelation Fe2+ by Caffeic Phenethyl Ester and Two of Its Derivatives. Computional and Theoretical Chemistry 2015, 1067, 135–147.
  • Yuzhen, C.; Huizhu, X.; Jie, Z.; Guizhao, L. Structure-Thermodynamics-Antioxidant Activity Relationship of Selected Natural Phenolic Acids and Derivatives: An Experimental and Theoretical Evaluation. Plos One 2015, 10, 012276–012295.
  • Demirbaş, N.; Uğurluoğlu, R. Synthesis and Antitumor Activities of Some 4-(1-Naphthylidenamino)-and 4-(1-Naphthylmethylamino)-1,2,4-Triazol-5-One Derivatives. Turkish Journal of Chemistry 2004, 28, 679–690.
  • Ikizler, A.A.; Uçar, F.; Yüksek, H.; Aytin, A.; Yasa, I.; Gezer, T. Synthesis and Antifungal Activity of Some New Arylidenamino Compounds. Acta Poloniae Pharmaceutica Drug Research 1997, 54, 135–140.
  • Bhat, A.R.; Bhat, G.V.; Shenoy, G.G. Synthesis and in-Vitro Antimicrobial Activity of New 1,2,4-Triazoles. Journal of Pharmacy and Pharmacology 2001, 53, 267–272.
  • Yüksek, H.; Küçük, M.; Alkan, M.; Bahçeci, Ş.; Kolaylı, S.; Ocak, Z.; Ocak, U.; Şahinbaş, E.; Ocak, M. Synthesis and Antioxidant Activities of Some New 4-(4-Hydroxybenzylidenamino)-4,5- Dihydro-1H-1,2,4-Triazol-5-One Derivatives with Their Acidic Properties. Asian Journal of Chemistry 2006, 18, 539–550.
  • Yüksek, H.; Kolaylı, S.; Küçük, M.; Yüksek, M.O.; Ocak, U.; Şahinbaş, E.; Sivrikaya, E.; Ocak, M. Synthesis and Antioxidant Activities of Some 4-Benzylidenamino-4,5-Dihydro-1H-1,2,4-Triazol-5-One Derivatives. Indian Journal of Chemistry 2006, 45B, 715–718.
  • Yüksek, H.; Demibaş, A.; Ikizler, A.; Johansson, C.B.; Çelik, C.; Ikizler, A.A. Synthesis and Antibacterial Activities of Some 4,5-Dihydro-1H-1,2,4-Triazol-5-Ones. Arzneimittel Forschung–Drug Research 1997, 47, 405–409.
  • Ünver, Y.; Meydanal, S.; Sancak, K.; Ünlüer, D.; Ustabas, R.; Dügdü, E. Synthesis, Cristal Structure and Antioxidant Properties of Novel 1,2,4-Triazol-5-Ones Containing 3,4-Dimethoxyphenyl and 3,4 Dihydroxyphenyl Moiety. Turkish Journal of Chemistry 2011, 35, 265–277.
  • Bikélé, M.D.; Zobo, J.M.; Lissouck, D.; Younang, E.; Nono, J.H.; Mbaze, L.M. DFT Investigation of Chelation of Divalent Cations by Some 4-Benzylidenamino-4,5-Dihydro-1h-1,2,4-Triazol-5-One Derivatives. Journal of Chemistry and Chemical Engineering 2015, 9, 1–14.
  • Stepanć, V.; Trošelj, K.G.; Lučić, B.; Markoviç, Z.; Amić, D. Bond Dissociation Energy As General for Flavonoid Radical Scavenging Activity. Food Chemistry 2013, 141, 1562–1570.
  • Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; et al. Gaussian 09 2009: Revision A.2. Gaussian, Inc.: Walllingford, CT.
  • Becke, A.D. Density-Functional Thermochemistry. III. The Role of Exact Exchange. Journal of Chemical Physics 1993, 98, 5648–5652.
  • Binley, J.S.; Pople, J.A.; Hehre, W.J. Self Consistent Molecular Orbital Method. 21. Small Split-Valence Basis Sets for First-Row Elements. Journal of the American Chemical Society 1980, 102, 939–947.
  • Cances, E.; Mennucci, B.; Tomasi, J. A New Integral Equation for Polarizable Model: Theoretical Background and Applications to Isotropic and Anisotropic Dielectrics. Journal of Chemical Physic 1997, 107, 3032–3041.
  • Bartmess, J.E. Thermodynamic of the Electron and the Proton. Journal of Physical Chemistry 1994, 98, 6420–6424.
  • Rimarčik, J.; Lukeš, V.; Klein, E.; Ilçin, M. Study of the Solvent Effect on the Enthalpies of Hemolytic and Heterolytic N-H Bond Cleavage in P-Phenyllenediamine and Tetracyano-P-Phenylenediamine. Journal of Molecular Structure (Theochem) 2010, 952, 25–30.
  • Hwang, S.; Chung, D.S. Calculation of the Solvation Free Energy of the Proton in Methanol. Bulletin of Korean Chemistry Society 2005, 26, 589–593.
  • Tissandier, M.D.; Cowen, K.A.; Feng, W.Y.; Gundlach, E.; Cohen, M.H.; Earhart, A.D.; Coe, J.V.; Tuttle, T.R.Jr. The Proton’s Absolute Aqueous Enthalpy and Gibbs Free Energy of Solvation from Cluster-Ion Solvation Data. The Journal of the Physical Chemistry. A 1998, 102(40), 7787–7794.
  • Jortener, J.; Noyes, R.M. Some Thermodynamic Properties of the Hydrated Electron. Journal of Physical Chemistry 1966, 70(3), 770–774.
  • Fifen, J.J.; Dhaouadi, Z.; Nsangou, M.; Holtomo, O.; Jaidane, N. Proton-Coupled Electron Transfer in the Reaction of 3,4-Dihydroxyphenylpyruvic Acid with Reactive Species in Various Media. International Journal of Chemical Physics 2015 2015, 1–3.
  • Çoruh, U.; Kahveci, B.; Şaşmaz, S.; Ağar, E.; Kim, Y. 1-Acettyl-4-(P-Chlorobenzylideneamino)-3-Methyl-4,5-Dihydro-1H-1,2,4 Triazol-5-One. Acta Crystallography Sect E 2003, 59, 0530–0532.
  • Wright, J.S.; Shadnia, H.; Chepelev, L.L. Stability of Carbon-Centered Radicals: Effect of Functional Group on the Energetic of Addition of Molecular Oxygen. Journal of Computational Chemistry 2008, 30, 1016–1026.
  • Holtomo, O.; Nsangou, M.; Fifen, J.J.; Motapon, O. DFT Study of the Solvent Effects ON The Structure, UV-Vis Spectra and the Antioxidant Activity of Caffeic Acid Phenethyl Ester and Some of Its Derivatives. Journal of Chemistry and Chemical Engineering 2013, 7, 910–923.
  • Clemens, O.; Basters, M.; Wild, M.; Wilbrand, S.; Reichert, C.; Bauer, M.; Springborg, M.; Jung, G. Solvent Effects on the Absorption/Emission Spectra of An Organic Chromophore. Journal of Molecular Structure (Theochem) 2008, 866, 15–20.
  • Jin, R. A DFT Study of the Radical Scavenging Activity of Juglone and Its Derivatives. Journal of Molecular Structure (Theochem) 2010, 939, 9–13.
  • Lu, Z.; Nie, G.; Belton, P.S.; Tang, H.; Zhao, B. Structure-Activity Relationship Analysis of Antioxidant Ability and Neuroprotective Effect of Gallic Acid Derivatives. Neurochemistry International 2006, 48, 263–274.
  • Kagan, V.E.; Elena, A.; Serbinova, L.P.; Recycling and Antioxidant Activity of Tocopherol Homologs of Differing Hydrocarbon Chain Lengths in Liver Microsomes. Archives of Biochemistry and Biophysic Biochemistry 1990, 282, 221–225.
  • Zang, H.-Y.; Structure-Activity Relationships and Rational Design Strategies for Radical-Scavenging Antioxidants. Current Computer-Aided Drug Design 2005, 1, 257–273.
  • Lengyel, J.; Rimarčik, J.; Vagánek, A.; Klein, E. On the Radical Scavenging Activity of Isoflavones: Thermodynamics of O-H Bond Cleavage. Physical Chemistry. Chemical Physic 2013, 15, 10895–10903.
  • Xue, Y.S.; Zheng, Y.G.; Zhang, L.; Wu, W.Y.; Yu, D.; Liu, Y. Theoretical Study on the Antioxidant Properties of 2-Hydroxychalcone: H-Atom Vs. Electron Transfer Mechanism. Journal of Molecular Modeling 2013, 19, 3851–3862.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.