Adrenaline and noradrenaline: Protectors against oxidative stress or molecular targets?

Journal of Physical Chemistry B

Volumn 119, Issue 8, 2015, Pages 3479-3491

  Álvarez Diduk, Ruslán ^a   Galano, Annia ^a  

^a DEPARTAMENTO DE QUÍMICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; DENSITY FUNCTIONAL THEORY; FREE RADICAL REACTIONS; FREE RADICALS; HORMONES; METAL IONS; MOLECULAR PHYSICS; OXIDATIVE STRESS;

BENEFICIAL EFFECTS; FREE RADICAL SCAVENGERS; HYDROGEN TRANSFER; MOLECULAR TARGETS; PEROXYL RADICAL; REACTION MECHANISM; REFERENCE COMPOUNDS; STRUCTURAL MODIFICATIONS;

NOREPINEPHRINE;

6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID; CHELATING AGENT; CHROMAN DERIVATIVE; COPPER; EPINEPHRINE; HYDROGEN; ION; NORADRENALIN; PERHYDROXYL RADICAL; PEROXIDE; PROTON; SCAVENGER; SOLUTION AND SOLUBILITY; WATER;

CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; DRUG EFFECTS; ELECTRON; OXIDATIVE STRESS; SOLUTION AND SOLUBILITY;

CHELATING AGENTS; CHROMANS; COMPUTER SIMULATION; COPPER; ELECTRONS; EPINEPHRINE; FREE RADICAL SCAVENGERS; HYDROGEN; IONS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NOREPINEPHRINE; OXIDATIVE STRESS; PEROXIDES; PROTONS; SOLUTIONS; WATER;

EID: 84923878637     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.5b00052     Document Type: Article

References (141)

1. Sayre, L. M.; Perry, G.; Smith, M. A. Oxidative stress and neurotoxicity Chem. Res. Toxicol. 2008, 21, 172-188
2. Shadab, M.; Agrawal, D. K.; Aslam, M.; Islam, N.; Ahmad, Z. Occupational health hazards among sewage workers: Oxidative stress and deranged lung functions J. Clin. Diagn. Res. 2014, 8, BC11-BC13
3. Zhao, W.; Gan, X.; Su, G.; Wanling, G.; Li, S.; Hei, Z.; Yang, C.; Wang, H. The interaction between oxidative stress and mast cell activation plays a role in acute lung injuries induced by intestinal ischemia-reperfusion J. Surg. Res. 2014, 187, 542-552
4. Ghasemzadeh, N.; Patel, R. S.; Eapen, D. J.; Veledar, E.; Kassem, H. A.; Manocha, P.; Khayata, M.; Zafari, A. M.; Sperling, L.; Jones, D. P. Oxidative stress is associated with increased pulmonary artery systolic pressure in humans Hypertension 2014, 63, 1270-1275
5. Yang, S. K.; Xiao, L.; Li, J.; Liu, F.; Sun, L. Oxidative stress, a common molecular pathway for kidney disease: Role of the redox enzyme p66shc Renal Failure 2014, 36, 313-320
6. Aruna, G.; Ambika Devi, K. Oxidative stress in chronic renal failure Int. J. Pharma Bio Sci. 2014, 5, B127-B133
7. Araujo, A. M.; Reis, E. A.; Athanazio, D. A.; Ribeiro, G. S.; Hagan, J. E.; Araujo, G. C.; Damiao, A. O.; Couto, N. S.; Ko, A. I.; Noronha-Dutra, A. Oxidative stress markers correlate with renal dysfunction and thrombocytopenia in severe leptospirosis Am. J. Trop. Med. Hyg. 2014, 90, 719-723
8. Rosenstein, R. E.; Pandi-Perumal, S. R.; Srinivasan, V.; Spence, D. W.; Brown, G. M.; Cardinali, D. P. Melatonin as a therapeutic tool in ophthalmology: Implications for glaucoma and uveitis J. Pineal Res. 2010, 49, 1-13
9. Uchino, Y.; Kawakita, T.; Ishii, T.; Ishii, N.; Tsubota, K. A new mouse model of dry eye disease: Oxidative stress affects functional decline in the lacrimal gland Cornea 2012, 31, S63-S67
10. Kaur, J.; Kukreja, S.; Kaur, A.; Malhotra, N.; Kaur, R. The oxidative stress in cataract patients J. Clin. Diagn. Res. 2012, 6, 1629-1632
11. Veselinovic, M.; Barudzic, N.; Vuletic, M.; Zivkovic, V.; Tomic-Lucic, A.; Djuric, D.; Jakovljevic, V. Oxidative stress in rheumatoid arthritis patients: Relationship to diseases activity Mol. Cell. Biochem. 2014, 391, 225-232
12. Kundu, S.; Ghosh, P.; Datta, S.; Ghosh, A.; Chattopadhyay, S.; Chatterjee, M. Oxidative stress as a potential biomarker for determining disease activity in patients with rheumatoid arthritis Free Radical Res. 2012, 46, 1482-1489
13. Wruck, C. J.; Fragoulis, A.; Gurzynski, A.; Brandenburg, L. O.; Kan, Y. W.; Chan, K.; Hassenpflug, J.; Freitag-Wolf, S.; Varoga, D.; Lippross, S. Role of oxidative stress in rheumatoid arthritis: Insights from the nrf2-knockout mice Ann. Rheum. Dis. 2011, 70, 844-850
14. Braekke, K.; Harsem, N. K.; Staff, A. C. Oxidative stress and antioxidant status in fetal circulation in preeclampsia Pediatr. Res. 2006, 60, 560-564
15. Hracsko, Z.; Orvos, H.; Novak, Z.; Pal, A.; Varga, I. S. Evaluation of oxidative stress markers in neonates with intra-uterine growth retardation Redox Rep. 2008, 13, 11-16
16. Mert, I.; Oruc, A. S.; Yuksel, S.; Cakar, E. S.; Buyukkagnici, U.; Karaer, A.; Danisman, N. Role of oxidative stress in preeclampsia and intrauterine growth restriction J. Obstet. Gynaecol. Res. 2012, 38, 658-664
17. Wang, J.; Li, J. Z.; Lu, A. X.; Zhang, K. F.; Li, B. J. Anticancer effect of salidroside on a549 lung cancer cells through inhibition of oxidative stress and phospho-p38 expression Oncol. Lett. 2014, 7, 1159-1164
18. Granados-Principal, S.; El-Azem, N.; Pamplona, R.; Ramirez-Tortosa, C.; Pulido-Moran, M.; Vera-Ramirez, L.; Quiles, J. L.; Sanchez-Rovira, P.; Naudí, A.; Portero-Otin, M. Hydroxytyrosol ameliorates oxidative stress and mitochondrial dysfunction in doxorubicin-induced cardiotoxicity in rats with breast cancer Biochem. Pharmacol. 2014, 90, 25-33
19. Tekiner-Gulbas, B.; Westwell, A. D.; Suzen, S. Oxidative stress in carcinogenesis: New synthetic compounds with dual effects upon free radicals and cancer Curr. Med. Chem. 2013, 20, 4451-4459
20. Halliwell, B. Role of free radicals in the neurodegenerative diseases: Therapeutic implications for antioxidant treatment Drugs Aging 2001, 18, 685-716
21. López, N.; Tormo, C.; De Blas, I.; Llinares, I.; Alom, J. Oxidative stress in alzheimers disease and mild cognitive impairment with high sensitivity and specificity J. Alzheimers Dis. 2013, 33, 823-829
22. Pohanka, M. Alzheimers disease and oxidative stress: A review Curr. Med. Chem. 2014, 21, 356-364
23. Yana, M. H.; Wang, X.; Zhu, X. Mitochondrial defects and oxidative stress in Alzheimer disease and Parkinson disease Free Radical Biol. Med. 2013, 62, 90-101
24. Eskici, G.; Axelsen, P. H. Copper and oxidative stress in the pathogenesis of Alzheimers disease Biochemistry 2012, 51, 6289-6311
25. Pimentel, C.; Batista-Nascimento, L.; Rodrigues-Pousada, C.; Menezes, R. A. Oxidative stress in Alzheimers and Parkinsons diseases: Insights from the yeast saccharomyces cerevisiae Oxid. Med. Cell. Longevity 2012, 2012 132146
26. Schrag, M.; Mueller, C.; Zabel, M.; Crofton, A.; Kirsch, W. M.; Ghribi, O.; Squitti, R.; Perry, G. Oxidative stress in blood in Alzheimers disease and mild cognitive impairment: A meta-analysis Neurobiol. Dis. 2013, 59, 100-110
27. Matsuda, M.; Shimomura, I. Roles of adiponectin and oxidative stress in obesity-associated metabolic and cardiovascular diseases Rev. Endocr. Metab. Disord. 2014, 15, 1-10
28. Eren, E.; Ellidag, H. Y.; Cekin, Y.; Ayoglu, R. U.; Sekercioglu, A. O.; Yilmaz, N. Heart valve disease: The role of calcidiol deficiency, elevated parathyroid hormone levels and oxidative stress in mitral and aortic valve insufficiency Redox Rep. 2014, 19, 34-39
29. Şerban, C.; Drəgan, S. The relationship between inflammatory and oxidative stress biomarkers, atherosclerosis and rheumatic diseases Curr. Pharm. Des. 2014, 20, 585-600
30. Zampetaki, A.; Dudek, K.; Mayr, M. Oxidative stress in atherosclerosis: The role of micrornas in arterial remodeling Free Radical Biol. Med. 2013, 64, 69-77
31. Gulçin, I. Antioxidant activity of l -adrenaline: A structure-activity insight Chem.-Biol. Interact. 2009, 179, 71-80
32. Cahova, M.; Palenickova, E.; Papackova, Z.; Dankova, H.; Skop, V.; Kazdova, L. Epinephrine-dependent control of glucose metabolism in white adipose tissue: The role of α- and β-adrenergic signalling Exp. Biol. Med. 2012, 237, 211-218
33. Wu, J.; Ji, M. H.; Wang, Z. Y.; Zhu, W.; Yang, J. J.; Peng, Y. G. Blood pressure reduction induced by low dose of epinephrine via different routes in rats J. Cardiovasc. Pharmacol. 2013, 62, 325-328
34. Errasti, A. E.; Werneck De Avellar, M. C.; Daray, F. M.; Tramontano, J.; Luciani, L. I.; Lina Bard, M. J.; Maróstica, E.; Rothlin, R. P. Human umbilical vein vasoconstriction induced by epinephrine acting on α1b-adrenoceptor subtype Am. J. Obstet. Gynecol. 2003, 189, 1472-1480
35. Rawas-Qalaji, M. M.; Simons, F. E. R.; Simons, K. J. Sublingual epinephrine tablets versus intramuscular injection of epinephrine: Dose equivalence for potential treatment of anaphylaxis J. Allergy Clin. Immunol. 2006, 117, 398-403
36. Dennerlein, J. T. Anaphylaxis treatment: Ergonomics of epinephrine autoinjector design Am. J. Med. 2014, 127, S12-S16
37. Odek, Ç.; Kendirli, T.; Çipe, F.; Katlan, B.; Doʇu, F. Pressure-induced angioedema associated with endotracheal tube: Successful treatment with epinephrine in two cases Eur. J. Pediatr. 2012, 171, 1573-1575
38. Rodrigo, G. J.; Nannini, L. J. Comparison between nebulized adrenaline and β2 agonists for the treatment of acute asthma. A meta-analysis of randomized trials Am. J. Emerg. Med. 2006, 24, 217-222
39. Arntz, H. R.; Breckwoldt, J. Cardiac resuscitation: Epinephrine to treat cardiac arrest-A double-edged sword Nat. Rev. Cardiol. 2012, 9, 380-382
40. Foote, S. L.; Bloom, F. E.; Aston Jones, G. Nucleus locus ceruleus: New evidence of anatomical and physiological specificity Physiol. Rev. 1983, 63, 844-914
41. Meier, E.; Hertz, L.; Schousboe, A. Neurotransmitters as developmental signals Neurochem. Int. 1991, 19, 1-15
42. Lauder, J. M. Neurotransmitters as growth regulatory signals: Role of receptors and second messengers Trends Neurosci. 1993, 16, 233-240
43. Siciliano, R.; Fornai, F.; Bonaccorsi, I.; Domenici, L.; Bagnoli, P. Cholinergic and noradrenergic afferents influence the functional properties of the postnatal visual cortex in rats Visual Neurosci. 1999, 16, 1015-1028
44. Katsuki, H.; Izumi, Y.; Zorumski, C. F. Noradrenergic regulation of synaptic plasticity in the hippocampal ca1 region J. Neurophysiol. 1997, 77, 3013-3020
45. Briley, M. Noradrenergic mechanisms in Parkinsons disease Trends Pharmacol. Sci. 1993, 14, 33-34
46. Jhang, K. A.; Lee, E. O.; Kim, H. S.; Chong, Y. H. Norepinephrine provides short-term neuroprotection against aβ1-42 by reducing oxidative stress independent of Nrf2 activation Neurobiol. Aging 2014, 35, 2465-2473
47. Troadec, J. D.; Marien, M.; Darios, F.; Hartmann, A.; Ruberg, M.; Colpaert, F.; Michel, P. P. Noradrenaline provides long-term protection to dopaminergic neurons by reducing oxidative stress J. Neurochem. 2001, 79, 200-210
48. Medina, M. E.; Galano, A.; Alvarez-Idaboy, J. R. Theoretical study on the peroxyl radicals scavenging activity of esculetin and its regeneration in aqueous solution Phys. Chem. Chem. Phys. 2014, 16, 1197-1207
49. Galano, A.; Alvarez-Idaboy, J. R.; Francisco-Márquez, M.; Medina, M. E. A quantum chemical study on the free radical scavenging activity of tyrosol and hydroxytyrosol Theor. Chem. Acc. 2012, 131, 1-12
50. León-Carmona, J. R.; Alvarez-Idaboy, J. R.; Galano, A. On the peroxyl scavenging activity of hydroxycinnamic acid derivatives: Mechanisms, kinetics, and importance of the acid-base equilibrium Phys. Chem. Chem. Phys. 2012, 14, 12534-12543
51. Galano, A.; Pérez-González, A. On the free radical scavenging mechanism of protocatechuic acid, regeneration of the catechol group in aqueous solution Theor. Chem. Acc. 2012, 131, 1-13
52. Pérez-González, A.; Galano, A.; Alvarez-Idaboy, J. R. Dihydroxybenzoic acids as free radical scavengers: Mechanisms, kinetics, and trends in activity New J. Chem. 2014, 38, 2639-2652
53. Galano, A.; Francisco Marquez, M.; Pérez-González, A. Ellagic acid: An unusually versatile protector against oxidative stress Chem. Res. Toxicol. 2014, 27, 904-918
54. Medina, M. E.; Iuga, C.; álvarez-Idaboy, J. R. Antioxidant activity of fraxetin and its regeneration in aqueous media. A density functional theory study RSC Adv. 2014, 4, 52920-52932
55. Medina, M. E.; Iuga, C.; Alvarez-Idaboy, J. R. Antioxidant activity of propyl gallate in aqueous and lipid media: A theoretical study Phys. Chem. Chem. Phys. 2013, 15, 13137-13146
56. Cordova-Gomez, M.; Galano, A.; Alvarez-Idaboy, J. R. Piceatannol, a better peroxyl radical scavenger than resveratrol RSC Adv. 2013, 3, 20209-20218
57. Caicedo, C.; Iuga, C.; Castañeda-Arriaga, R.; Alvarez-Idaboy, J. R. Antioxidant activity of selected natural polyphenolic compounds from soybean via peroxyl radical scavenging RSC Adv. 2014, 4, 38918-38930
58. Weinshenker, D. Functional consequences of locus coeruleus degeneration in Alzheimers disease Curr. Alzheimer Res. 2008, 5, 342-345
59. Zarow, C.; Lyness, S. A.; Mortimer, J. A.; Chui, H. C. Neuronal loss is greater in the locus coeruleus than nucleus basalis and substantia nigra in Alzheimer and Parkinson diseases Arch. Neurol. 2003, 60, 337-341
60. Grudzien, A.; Shaw, P.; Weintraub, S.; Bigio, E.; Mash, D. C.; Mesulam, M. M. Locus coeruleus neurofibrillary degeneration in aging, mild cognitive impairment and early alzheimers disease Neurobiol. Aging 2007, 28, 327-335
61. Matthews, K. L.; Chen, C. P. L. H.; Esiri, M. M.; Keene, J.; Minger, S. L.; Francis, P. T. Noradrenergic changes, aggressive behavior, and cognition in patients with dementia Biol. Psychiatry 2002, 51, 407-416
62. Hammerschmidt, T.; Kummer, M. P.; Terwel, D.; Martinez, A.; Gorji, A.; Pape, H. C.; Rommelfanger, K. S.; Schroeder, J. P.; Stoll, M.; Schultze, J. Selective loss of noradrenaline exacerbates early cognitive dysfunction and synaptic deficits in app/ps1 mice Biol. Psychiatry 2013, 73, 454-463
63. Heneka, M. T.; Galea, E.; Gavriluyk, V.; Dumitrescu-Ozimek, L.; Daeschner, J.; OBanion, M. K.; Weinberg, G.; Klockgether, T.; Feinstein, D. L. Noradrenergic depletion potentiates β-amyloid-induced cortical inflammation: Implications for Alzheimers disease J. Neurosci. 2002, 22, 2434-2442
64. Jardanhazi-Kurutz, D.; Kummer, M. P.; Terwel, D.; Vogel, K.; Thiele, A.; Heneka, M. T. Distinct adrenergic system changes and neuroinflammation in response to induced locus ceruleus degeneration in app/ps1 transgenic mice Neuroscience 2011, 176, 396-407
65. Kalinin, S.; Gavrilyuk, V.; Polak, P. E.; Vasser, R.; Zhao, J.; Heneka, M. T.; Feinstein, D. L. Noradrenaline deficiency in brain increases β-amyloid plaque burden in an animal model of Alzheimers disease Neurobiol. Aging 2007, 28, 1206-1214
66. Chiari, A.; Li, X. H.; Xu, Z.; Pan, H. L.; Eisenach, J. C. Formation of 6-nitro-norepinephrine from nitric oxide and norepinephrine in the spinal cord and its role in spinal analgesia Neuroscience 2000, 101, 189-196
67. Tsunoda, M.; Uchino, E.; Imai, K.; Funatsu, T. Oxidative stress increases 6-nitronorepinephrine and 6-nitroepinephrine concentrations in rat brain Biomed. Chromatogr. 2008, 22, 572-574
68. Manini, P.; Panzella, L.; Napolitano, A.; DIschia, M. Oxidation chemistry of norepinephrine: Partitioning of the o-quinone between competing cyclization and chain breakdown pathways and their roles in melanin formation Chem. Res. Toxicol. 2007, 20, 1549-1555
69. Manini, P.; Pezzella, A.; Panzella, L.; Napolitano, A.; DIschia, M. New insight into the oxidative chemistry of noradrenaline: Competitive o-quinone cyclisation and chain fission routes leading to an unusual 4-[bis-(1H-5,6-dihydroxyindol-2-yl)methyl]-1,2-dihydroxybenzene derivative Tetrahedron 2005, 61, 4075-4080
70. Napolitano, A.; Manini, P.; DIschia, M. Oxidation chemistry of catecholamines and neuronal degeneration: An update Curr. Med. Chem. 2011, 18, 1832-1845
71. Terpinc, P.; Abramovič, H. A kinetic approach for evaluation of the antioxidant activity of selected phenolic acids Food Chem. 2010, 121, 366-371
72. Sies, H. Oxidative stress: Oxidants and antioxidants Exp. Physiol. 1997, 82, 291-295
73. Masuda, T.; Yamada, K.; Maekawa, T.; Takeda, Y.; Yamaguchi, H. Antioxidant mechanism studies on ferulic acid: Isolation and structure identification of the main antioxidation product from methyl ferulate Food Sci. Technol. Res. 2006, 12, 173-177
74. Masuda, T.; Yamada, K.; Maekawa, T.; Takeda, Y.; Yamaguchi, H. Antioxidant mechanism studies on ferulic acid: Identification of oxidative coupling products from methyl ferulate and linoleate J. Agric. Food Chem. 2006, 54, 6069-6074
75. Rose, R. C.; Bode, A. M. Biology of free radical scavengers: An evaluation of ascorbate FASEB J. 1993, 7, 1135-1142
76. Galano, A.; Tan, D. X.; Reiter, R. J. Melatonin as a natural ally against oxidative stress: A physicochemical examination J. Pineal Res. 2011, 51, 1-16
77. •: The forgotten radical DNA Cell Biol. 2002, 21, 251-257
78. Andrews, N. C. Mining copper transport genes Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 6543-6545
79. Brewer, G. J. Iron and copper toxicity in diseases of aging, particularly atherosclerosis and Alzheimers disease Exp. Biol. Med. 2007, 232, 323-335
80. Gaetke, L. M.; Chow, C. K. Copper toxicity, oxidative stress, and antioxidant nutrients Toxicology 2003, 189, 147-163
81. Aruoma, O. I.; Halliwell, B.; Gajewski, E.; Dizdaroglu, M. Copper-ion-dependent damage to the bases in DNA in the presence of hydrogen peroxide Biochem. J. 1991, 273, 601-604
82. Letelier, M. E.; Sánchez-Jofré, S.; Peredo-Silva, L.; Cortés-Troncoso, J.; Aracena-Parks, P. Mechanisms underlying iron and copper ions toxicity in biological systems: Pro-oxidant activity and protein-binding effects Chem.-Biol. Interact. 2010, 188, 220-227
83. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Gaussian 09; Gaussian: Wallingford, CT, USA, 2009.
84. Zhao, Y.; Truhlar, D. G. The m06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four m06-class functionals and 12 other functionals Theor. Chem. Acc. 2008, 120, 215-241
85. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions J. Phys. Chem. B 2009, 113, 6378-6396
86. Kumar, M.; Busch, D. H.; Subramaniam, B.; Thompson, W. H. Role of tunable acid catalysis in decomposition of α-hydroxyalkyl hydroperoxides and mechanistic implications for tropospheric chemistry J. Phys. Chem. A 2014, 118, 9701-9711
87. Alarcón, P.; Bohn, B.; Zetzsch, C.; Rayez, M. T.; Rayez, J. C. Reversible addition of the oh radical to p-cymene in the gas phase: Multiple adduct formation. Part 2 Phys. Chem. Chem. Phys. 2014, 16, 17315-17326
88. Denegri, B.; Matić, M.; Kronja, O. A DFT-based model for calculating solvolytic reactivity. The nucleofugality of aliphatic carboxylates in terms of nf parameters Org. Biomol. Chem. 2014, 12, 5698-5709
89. Parkhomenko, D. A.; Edeleva, M. V.; Kiselev, V. G.; Bagryanskaya, E. G. pH-sensitive C-ON bond homolysis of alkoxyamines of imidazoline series: A theoretical study J. Phys. Chem. B 2014, 118, 5542-5550
90. Xie, H. B.; Li, C.; He, N.; Wang, C.; Zhang, S.; Chen, J. Atmospheric chemical reactions of monoethanolamine initiated by OH radical: Mechanistic and kinetic study Environ. Sci. Technol. 2014, 48, 1700-1706
91. 2CHOCHFO: Thermal decomposition vs. Oxidation New J. Chem. 2014, 38, 2813-2822
92. 2: A computational study of the reaction mechanism and kinetics. Theor. Chem. Acc. 2013, 132 1375.
93. Mandal, D.; Sahu, C.; Bagchi, S.; Das, A. K. Kinetics and mechanism of the tropospheric oxidation of vinyl acetate initiated by OH radical: A theoretical study J. Phys. Chem. A 2013, 117, 3739-3750
94. 2 addition into the MACR + OH master equation J. Phys. Chem. A 2012, 116, 5317-5324
95. Zhao, Y.; Truhlar, D. G. How well can new-generation density functionals describe the energetics of bond-dissociation reactions producing radicals? J. Phys. Chem. A 2008, 112, 1095-1099
96. Galano, A.; Alvarez-Idaboy, J. R. Kinetics of radical-molecule reactions in aqueous solution: A benchmark study of the performance of density functional methods J. Comput. Chem. 2014, 35, 2019-2026
97. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions J. Chem. Theory Comput. 2006, 2, 364-382
98. Okuno, Y. Theoretical investigation of the mechanism of the Baeyer-Villiger reaction in nonpolar solvents Chem.-Eur. J. 1997, 3, 212-218
99. Benson, S. W. The foundations of chemical kinetics; McGraw-Hill: New York, 1960.
100. Eyring, H. The activated complex in chemical reactions J. Chem. Phys. 1935, 3, 63-71
101. Evans, M. G.; Polanyi, M. Some applications of the transition state method to the calculation of reaction velocities, especially in solution Trans. Faraday Soc. 1935, 31, 875-894
102. Truhlar, D. G.; Garrett, B. C.; Klippenstein, S. J. Current status of transition-state theory J. Phys. Chem. 1996, 100, 12771-12800
103. Kuppermann, A.; Truhlar, D. G. Exact tunneling calculations J. Am. Chem. Soc. 1971, 93, 1840-1851
104. Galano, A.; Alvarez-Idaboy, J. R. A computational methodology for accurate predictions of rate constants in solution: Application to the assessment of primary antioxidant activity J. Comput. Chem. 2013, 34, 2430-2445
105. Jameson, R. F.; Neillie, W. F. S. 439. Complexes formed by adrenaline and related compounds with transition-metal ions. Part I. Acid dissociation constants of the ligands J. Chem. Soc. 1965, 2391-2395
106. Kappe, T.; Armstrong, M. D. Ultraviolet absorption spectra and apparent acidic dissociation constants of some phenolic amines J. Med. Chem. 1965, 8, 368-374
107. 2+ J. Inorg. Nucl. Chem. 1974, 36, 2151-2154
108. 1H nuclear magnetic resonance study of the deprotonation of l -dopa and adrenaline J. Chem. Soc., Perkin Trans. 2 1980, 1105-1110
109. Gergely, A.; Kiss, T.; Deák, G.; Sóvágó, I. Complexes of 3,4-dihydroxyphenyl derivatives IV. Equilibrium studies on some transition metal complexes formed with adrenaline and noradrenaline Inorg. Chim. Acta 1981, 56, 35-40
110. Jameson, R. F.; Kiss, T. The oxovanadyl(IV) catalysed oxidation of adrenaline by molecular oxygen J. Chem. Soc., Dalton Trans. 1986, 1833-1838
111. Gerard, C.; Chehhal, H. Stability of metal complexes with ligands of biological interest: Dopamine and adrenaline Bull. Soc. Chim. Fr. 1997, 134, 1069-1074
112. Corona-Avendaño, S.; Alarcón-Angeles, G.; Rojas-Hernández, A.; Romero-Romo, M. A.; Ramírez-Silva, M. T. Study on the stability of adrenaline and on the determination of its acidity constants Spectrochim. Acta, Part A 2005, 61, 305-311
113. 2+-ATP with biogenic amines J. Neurochem. 1972, 19, 1099-1116
114. Corona-Avendaño, S.; Rojas-Hernández, A.; Romero-Romo, M. A.; Pardavé, M. P.; Ramírez-Silva, M. T. Study on the stability of noradrenaline and on the determination of its acidity constants Spectrochim. Acta, Part A 2005, 61, 3139-3144
115. Belcastro, M.; Marino, T.; Russo, N.; Toscano, M. Structural and electronic characterization of antioxidants from marine organisms Theor. Chem. Acc. 2006, 115, 361-369
116. Leopoldini, M.; Russo, N.; Chiodo, S.; Toscano, M. Iron chelation by the powerful antioxidant flavonoid quercetin J. Agric. Food Chem. 2006, 54, 6343-6351
117. Leopoldini, M.; Rondinelli, F.; Russo, N.; Toscano, M. Pyranoanthocyanins: A theoretical investigation on their antioxidant activity J. Agric. Food Chem. 2010, 58, 8862-8871
118. Leopoldini, M.; Russo, N.; Toscano, M. The molecular basis of working mechanism of natural polyphenolic antioxidants Food Chem. 2011, 125, 288-306
119. Chiodo, S. G.; Leopoldini, M.; Russo, N.; Toscano, M. The inactivation of lipid peroxide radical by quercetin. A theoretical insight Phys. Chem. Chem. Phys. 2010, 12, 7662-7670
120. •) in alcohols J. Org. Chem. 2003, 68, 3433-3438
121. Litwinienko, G.; Ingold, K. U. Abnormal solvent effects on hydrogen atom abstraction. 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer J. Org. Chem. 2004, 69, 5888-5896
122. Litwinienko, G.; Ingold, K. U. Abnormal solvent effects on hydrogen atom abstraction. 3. Novel kinetics in sequential proton loss electron transfer chemistry J. Org. Chem. 2005, 70, 8982-8990
123. Litwinienko, G.; Ingold, K. U. Solvent effects on the rates and mechanisms of reaction of phenols with free radicals Acc. Chem. Res. 2007, 40, 222-230
124. Alberto, M. E.; Russo, N.; Grand, A.; Galano, A. A physicochemical examination of the free radical scavenging activity of trolox: Mechanism, kinetics and influence of the environment Phys. Chem. Chem. Phys. 2013, 15, 4642-4650
125. Iuga, C.; Alvarez-Idaboy, J. R.; Russo, N. Antioxidant activity of trans-resveratrol toward hydroxyl and hydroperoxyl radicals: A quantum chemical and computational kinetics study J. Org. Chem. 2012, 77, 3868-3877
126. Galano, A. On the direct scavenging activity of melatonin towards hydroxyl and a series of peroxyl radicals Phys. Chem. Chem. Phys. 2011, 13, 7178-7188
127. Marino, T.; Galano, A.; Russo, N. Radical scavenging ability of gallic acid toward OH and OOH radicals. Reaction mechanism and rate constants from the density functional theory J. Phys. Chem. B 2014, 118, 10380-10389
128. Iuga, C.; Alvarez-Idaboy, J. R.; Vivier-Bunge, A. Ros initiated oxidation of dopamine under oxidative stress conditions in aqueous and lipidic environments J. Phys. Chem. B 2011, 115, 12234-12246
129. Martínez, A.; Galano, A.; Vargas, R. Free radical scavenger properties of α-mangostin: Thermodynamics and kinetics of hat and raf mechanisms J. Phys. Chem. B 2011, 115, 12591-12598
130. Lloyd, R. V.; Hanna, P. M.; Mason, R. P. The origin of the hydroxyl radical oxygen in the fenton reaction Free Radical Biol. Med. 1997, 22, 885-888
131. Bentes, A. L. A.; Borges, R. S.; Monteiro, W. R.; De Macedo, L. G. M.; Alves, C. N. Structure of dihydrochalcones and related derivatives and their scavenging and antioxidant activity against oxygen and nitrogen radical species Molecules 2011, 16, 1749-1760
132. Kabanda, M. M. Antioxidant activity of rooperol investigated through Cu (I and II) chelation ability and the hydrogen transfer mechanism: A DFT study Chem. Res. Toxicol. 2012, 25, 2153-2166
133. Galano, A.; Medina, M. E.; Tan, D. X.; Reiter, R. J. Melatonin and its metabolites as copper chelating agents and their role in inhibiting oxidative stress: A physicochemical analysis J. Pineal Res. 2014, 10.1111/jpi.12196
134. Bryantsev, V. S.; Diallo, M. S.; Goddard, W. A., III. Computational study of copper(ii) complexation and hydrolysis in aqueous solutions using mixed cluster/continuum models J. Phys. Chem. A 2009, 113, 9559-9567
135. Fujii T.,Moynier F.,Abe M.,Nemoto K.,Albarede F. Copper isotope fractionation between aqueous compounds relevant to low temperature geochemistry and biology Geochim. Cosmochim. Acta 2013 110 29-44
136. Fulton, J. L.; Hoffmann, M. M.; Darab, J. G. An X-ray absorption fine structure study of copper(I) chloride coordination structure in water up to 325°C Chem. Phys. Lett. 2000, 330, 300-308
137. Fulton, J. L.; Hoffmann, M. M.; Darab, J. G.; Palmer, B. J.; Stern, E. A. Copper(I) and copper(II) coordination structure under hydrothermal conditions at 325 °C: An X-ray absorption fine structure and molecular dynamics study J. Phys. Chem. A 2000, 104, 11651-11653
138. Rojas, A.; González, I. Relationship of two-dimensional predominance-zone diagrams with conditional constants for complexation equilibria Anal. Chim. Acta 1986, 187, 279-285
139. Rojas-Hernández, A.; Ramírez, M. T.; Ibáñez, J. G.; González, I. Relationship of multidimensional predominance-zone diagrams with multiconditional constants for complexation equilibria Anal. Chim. Acta 1991, 246, 435-442
140. + J. Phys. Chem. A 2005, 109, 10795-10797
141. Galano, A.; Medina, M. E.; Tan, D. X.; Reiter, R. J. Melatonin and its metabolites as copper chelating agents and their role in inhibiting oxidative stress: A physicochemical analysis J. Pineal Res. 2015, 58, 107-116