期刊
RSC ADVANCES
卷 11, 期 35, 页码 21433-21446出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ra04146k
关键词
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资金
- Vietnam National Foundation for Science and Technology Development (NAFOSTED) [103.01-2019.380]
- USA National Science Foundation [ACI-10535]
- LABEX CaPPA (Chemical and Physical Properties of the Atmosphere) - French National Research Agency (ANR) through the PIA (Programme d'Investissement d'Avenir) [ANR-11-LABX-000501]
- Regional Council Hauts de France
- European Funds for Regional Economic Development
The antioxidant and UV absorption activities of three aaptamine derivatives were theoretically studied, showing their potential applications in pharmaceuticals and cosmetics as sunscreen and antioxidant ingredients.
Antioxidant and UV absorption activities of three aaptamine derivatives including piperidine[3,2-b]demethyl(oxy)aaptamine (C1), 9-amino-2-ethoxy-8-methoxy-3H-benzo[de][1,6]naphthyridine-3-one (C2), and 2-(sec-butyl)-7,8-dimethoxybenzo[de]imidazo[4,5,1-ij][1,6]-naphthyridin-10(9H)-one (C3) were theoretically studied by density functional theory (DFT). Direct antioxidant activities of C1-C3 were firstly evaluated via their intrinsic thermochemical properties and the radical scavenging activity of the potential antioxidants with the HOO/HO radicals via four mechanisms, including: hydrogen atom transfer (HAT), single electron transfer (SET), proton loss (PL) and radical adduct formation (RAF). Kinetic calculation reveals that HOO scavenging in water occurs via HAT mechanism with C1 (k(app), 7.13 x 10(6) M-1 s(-1)) while RAF is more dominant with C2 (k(app), 1.40 x 10(5) M-1 s(-1)) and C3 (k(app), 2.90 x 10(5) M-1 s(-1)). Antioxidant activity of aaptamine derivatives can be classified as C1 > C3 > C2. Indirect antioxidant properties based on Cu(i) and Cu(ii) ions chelating activity were also investigated in aqueous phase. All three studied compounds show spontaneous and favorable Cu(i) ion chelating activity with Delta G(0) being -15.4, -13.7, and -15.7 kcal mol(-1), whereas Delta G(0) for Cu(ii) chelation are -10.4, -10.8, and -2.2 kcal mol(-1) for C1, C2 and C3, respectively. In addition, all compounds show UVA and UVB absorption; in which the excitations are determined mostly as pi-pi* transition. Overall, the results suggest the potential applications of the aaptamines in pharmaceutics and cosmetics, i.e. as a sunscreen and antioxidant ingredient.
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