Radical scavenging activity of ascorbic acid analogs: kinetics and mechanisms

被引:16
作者
Ardjani, Taki Eddine Ahmed [1 ]
Raul Alvarez-Idaboy, Juan [2 ]
机构
[1] Univ Setif, Fac Sci, Dept Chem, Setif 19000, Algeria
[2] Univ Nacl Autonoma Mexico, Fac Quim, Dept Fis & Quim Teor, Mexico City 04510, DF, Mexico
关键词
Ascorbic acid analogs; Antioxidant activity; DFT calculations; Rate constants; PRINCIPLES-BASED METHOD; MILD COGNITIVE IMPAIRMENT; DENSITY-FUNCTIONAL THEORY; COMPLETE BASIS-SET; OXIDATIVE STRESS; AQUEOUS-SOLUTION; ALZHEIMERS-DISEASE; PK(A) VALUES; MYOCARDIAL-INFARCTION; ANTIOXIDANT MECHANISM;
D O I
10.1007/s00214-018-2252-x
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In the present work, the antioxidant activity of four ascorbic acid analogs has been studied at the M05-2X/6-31G+(d) computational level using the conventional transition state theory in different solvents, with different polarity and taking into account all possible mechanisms. The obtained results indicate that the antioxidant activity of the ascorbic acid analogs increases with the polarity of the environment. Additionally, their antioxidant activity is higher than ascorbic acid. This result is in line with experimental finding which supports the hypothesis that the analogs that had an endocyclic nitrogen atom instead of a ring oxygen may have a higher antioxidant activity than ascorbic acid. On the other hand, the results also indicate that compound 4 (designed by us) is predicted to be more antioxidant than ascorbic acid and the other analogs 1-3, in both lipid and aqueous solution. Finally, for the first time, pKa values, branching ratios and the rate constants for the reactions of ascorbic acid analogs with methylperoxyl radical CH3OO center dot are reported.
引用
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页数:8
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