The antioxidant activity of cynodontin was studied in the absence and the presence of free radical species. This in silico study was performed in water and benzene, with the aim to simulate polar and non-polar environment. To determine the most probable mechanism of antioxidant action, density functional theory (DFT) was employed. The change in reaction enthalpy of cynodontin with three different free radicals (hydroxyl, hydroperoxyl, and methyl peroxyl radical) were examined and presented. SET-PT (Single Electron Transfer – Proton Transfer) mechanism is not an operative mechanism of antioxidant action. The obtained results imply that the possible mechanism of antioxidant action in water is SPLET (Sequential Proton Loss Electron Transfer), while in benzene HAT (Hydrogen atom transfer) and SPLET are competitive mechanisms. The molecular docking study was performed in order to estimate the inhibition potency of the investigated compound toward human leukocyte elastase (HLE). The obtained results indicate that numerous interactions determine the inhibition activity towards the investigated protein.
Alberto M, Russo N, Grand A, Galano A. A physicochemical examination of the free radical scavenging activity of Trolox: mechanism, kinetics and influence of the environment. Physical chemistry chemical physics. 2013;(13):4642–50.
2.
Álvarez-Diduk R, Galano A. Adrenaline and noradrenaline: protectors against oxidative stress or molecular targets? The Journal of Physical Chemistry B. 2015;(8):3479–91.
3.
Journal of the Serbian Society for Computational Mechanics. 2020;69.
4.
Annen O, Egli R, Hasler R, Henzi B, Jakob H, Matzinger P. Replacement of disperse anthraquinone dyes. Review of Progress in Coloration and Related Topics. 1987;(1):72–85.
5.
Booth G. The Manufacture of Organic Colorants and Intermediates. Society of Dyers and Colourists. 1988;
6.
Frisch M, Trucks G, Schlegel H, Scuseria G, Robb M, Cheeseman J, et al.
7.
Galano A. Free radicals induced oxidative stress at a molecular level: the current status, challenges and perspectives of computational chemistry based protocols. Journal of the Mexican Chemical Society. 2015;(4):231–62.
8.
Galano A, Mazzone G, Alvarez-Diduk R, Marino T, Alvarez-Idaboy J, Russo N. Food antioxidants: chemical insights at the molecular level. Annual review of food science and technology. 2016;335–52.
9.
Gordon P, Gregory P. Organic chemistry in colour. 2012;
10.
Halliwell B, Gutteridge JMC. Free Radicals in Biology and Medicine. 1999.
11.
Halliwell B. Free radicals and other reactive species in disease. Els. 2001;1–9.
12.
Halliwell B. 2001;1–9.
13.
Hiemstra P, Van Wetering S, Stolk J. Neutrophil serine proteinases and defensins in chronic obstructive pulmonary disease: effects on pulmonary epithelium. European Respiratory Journal. 1998;(5):1200–8.
14.
Hochscherf J, Pietsch M, Tieu W, Kuan K, Abell A, Gütschow M, et al. Crystal structure of highly glycosylated human leukocyte elastase in complex with an S2′ site binding inhibitor. Acta Crystallographica Section F: Structural Biology Communications. 2018;(8):480–9.
15.
Morris G, Huey R, Lindstrom W, Sanner M, Belew R, Goodsell D, et al. Automated docking with selective receptor flexibility. Journal of computational chemistry. 2009;(16):2785–91.
16.
Petrović Z, Đorović J, Simijonović D, Petrović V, Marković Z. Experimental and theoretical study of antioxidative properties of some salicylaldehyde and vanillic Schiff bases. 2015;(31):24094–100.
17.
Renfrew A. Reactive dyes for cellulose: replacement of anthraquinone blues by triphenodioxazines. Rev Prog Coloration. 1985;15.
18.
Rimarčík J, Lukeš V, Klein E, Ilčin M. Study of the solvent effect on the enthalpies of homolytic and heterolytic N-H bond cleavage in p-phenylenediamine and tetracyano-pphenylenediamine. Journal of Molecular Structure: THEOCHEM. 2010;(1–3):25–30.
19.
Rose R, Bode A. Biology of free radical scavengers: an evaluation of ascorbate. The FASEB journal. 1993;(12):1135–42.
20.
Shore J. Colorants and auxiliaries. 1990;
21.
Sinha S, Watorek W, Karr S, Giles J, Bode W, Travis J. Primary structure of human neutrophil elastase. Proceedings of the National Academy of Sciences. 1987;(8):2228–32.
22.
Đorović J. Antioxidative and Inhibition Potency of Cynodontin, 70. 2020;
23.
Takahashi H, Nukiwa T, Yoshimura K, Quick C, Holmes M, Whang-Peng J, et al. Structure of the human neutrophil elastase gene. Journal of Biological Chemistry. 1988;(29):14739–47.
24.
Takano Y, Houk K. Benchmarking the conductor-like polarizable continuum model (CPCM) for aqueous solvation free energies of neutral and ionic organic molecules. Journal of Chemical Theory and Computation. 2005;(1):70–7.
25.
Taylor G. Natural dyes in textile applications. Review of Progress in Coloration and related topics. 1986;(1):53–61.
26.
Thomson RH. Naturally Occurring Quinones. 1971.
27.
Tošović J, Marković S, Milenković D, Marković Z. Solvation enthalpies and Gibbs energies of the proton and electron: influence of solvation models. Journal of the Serbian Society for Computational Mechanics. 2016;10(2):66–76.
28.
Walton P, Taylor G. The characterisation of dyes in textiles from archaeological excavations. Chromatogr And Analysis. 1991;
29.
Zhang H, Ji H. How vitamin E scavenges DPPH radicals in polar protic media. New journal of chemistry. 2006;(4):503–4.
30.
Zhao Y, Truhlar D. 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. Theoretical Chemistry Accounts. 2008;(1–3):215–41.
31.
Zollinger H. Synthesis, Properties and Applications of Organic Dyes and Pigments. Colour Chemistry. 1987;
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